Tag: M.W:100-200

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.54258-41-2,1,10-Phenanthrolin-5-amine,as a common compound, the synthetic route is as follows.

General procedure: 4.2.1.4. Method D. A stirred solution of the 5-amino-1,10-phenanthroline (195 mg, 1 mmol), the monosaccharide (3 mmol) and ca. 4 mg of (NH4)2SO4 in 16 mL of MeOH was heated at 65 C for 24 or 48 h. During this time a pale yellow precipitate was accumulated. The reaction mixture was cooled and the solid obtained was separated by filtration and washed with MeOH (2 x 10 mL) and H2O (2 x 10 mL) to eliminate excess of sugar and possible traces of the starting amine and/or other by-products as well to remove the (NH4)2SO4 salt, followed by Et2O. This protocol provided pure N-(1,10-phenanthrolin-5-yl)-beta-glycopyranosyl amines 2a, 2c and 2d. For derivatives 2b and 2e the starting sugar could not be completely removed and a subsequent purification was required. The product was preadsorbed on silica gel and purified by flash chromatography. After drying in vacuum the purity of the products was checked by TLC, 1H NMR and analytical data. Derivatives 2a-e were obtained as monohydrates and exhibited poor solubility in water and organic solvents., 54258-41-2

54258-41-2 1,10-Phenanthrolin-5-amine 606970, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Article; Duskova, Katerina; Gude, Lourdes; Arias-Perez, Maria-Selma; Tetrahedron; vol. 70; 5; (2014); p. 1071 – 1076;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13040-77-2,6-Chloro-2,2′-bipyridine,as a common compound, the synthetic route is as follows.

Example 1 Synthesis of Bipyridine-Pyrazole Ligand tBuOK (2g) was added to a suspension of pyrazole (1 g) in dmso (80 mL) and stirred until a clear solution has formed. 6-chloro-2,2′-bipyridine (1g, from HetCat) was added slowly by portion and the mixture heated at 140 C for 14 hours. After cooling down to room temperature, water was added and the precipitate filtered and wash with water. The compound was further purified by silica gel chromatography column using Ethyl acetate/diethyl ether as eluent, leading to an off-white crystalline solid (450 mg, yield 39 %). Spectroscopic analysis are as reported in the literature ()., 13040-77-2

As the paragraph descriping shows that 13040-77-2 is playing an increasingly important role.

Reference£º
Patent; Ecole Polytechnique Federale de Lausanne (EPFL); EP2492277; (2012); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.294-90-6,1,4,7,10-Tetraazacyclododecane,as a common compound, the synthetic route is as follows.

To a solution of cyclen (S4, 1.73 g, 10.0 mmol) and triethylamine (4.20 mL, 30.1 mmol)in CHCI3 (120 mL, freshly passed through A1203 (activated, neutral, Brockmann I)) at 0C was added dropwise a solution of di-tert-butyl dicarbonate (6.55 g, 30.0 mmol) inCHCl (100 mL, freshly passed through A1203 (activated, neutral, Brockmann I)) under N2. After the addition was complete, the resulting solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by flash column chromatography (silica gel, EtOAc:hexane = 3:2 ramping to EtOAc) to give S6 as a white foam (3.41 g, 72%).RF (EtOAc:hexane = 4:1) 0.63. IR vmax/cm1 3313, 2974, 2931, 2818, 1679, 1463, 1412,365, 1313, 1247, 1156, 1 046, 771, 736. 1H NMR (400 MHz, CDCI3) 5 1.45 (5, 1 8H, 2 x C(CH3)3), 1.47 (5, 9H, C(CH3)3), 2.78-2.92 (m, 4H, CH2NHCH2), 3.16-3.34 (m, 6H),3.34-3.50 (m, 2H), 3.55-3.75 (m, 4H) (total 12H, 3 x CH2N(Boc)CH2) (one secondary amine proton signal (NH) not observed). ?3C NMR (100 MHz, CDCI3) 5 28.1, 28.2, 28.3,28.4, 28.5, 44.7, 45.7, 48.8, 49.2, 50.3, 50.8, 78.9, 79.1, 155.1, 155.4 (eight carbon signals overlapping or obscured). MS (ESI) m/z 472.9 ([M+H], 27%), 495.0 ([M+Na], 99%), 967.1 ([2M+Na], 100%). The spectroscopic data were in agreement with those in the literature.3739, 294-90-6

294-90-6 1,4,7,10-Tetraazacyclododecane 64963, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; THE UNIVERSITY OF SYDNEY; RUTLEDGE, Peter; TODD, Matthew; TRICCAS, James Anthony; WO2014/153624; (2014); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4730-54-5,1,4,7-Triazacyclononane,as a common compound, the synthetic route is as follows.

(Example 7) Triazacyclononane (1.0 g, 7.74 mmol), triethylamine (5.1 g, 50 mmol) and anhydrous methylene chloride (100 mL) were added to a 200 mL three neck flask provided with a dripping funnel in an argon atmosphere. n-octanoic acid chloride (4.2 g, 25.8 mmol) was added to this mixture by the dripping funnel at room temperature, and the reaction mixture was stirred for two days at room temperature. This reaction mixture was washed with water (25 mL x 4), and next, the organic layer obtained was dried using anhydrous magnesium sulfate. After concentration, there was formation using silica gel column chromatography, and 1,4,7-tri(n-heptylcarbonyl)-1,4,7-triazacyclononane (3.14 g, 80% yield) was obtained. All of the 1,4,7-tri(n-heptylcarbonyl)-1,4,7-triazacyclononane was put into a 200 mL three neck flask provided with a reflux tube in an argon atmosphere, and a BH3¡¤THF solution (100 mmol, 100 mL) was added thereto and reflowed for one night. To break down the excess BH3¡¤THF, methanol was added slowly to the reaction mixture after allowing it to cool to room temperature, and after concentration, this was dissolved in 1-butanol (50 mL), water (50 mL) and concentrated hydrochloric acid (100 mL and reflowed for one night. The reaction mixture obtained was cooled in an ice bath, and a 48% aqueous solution of sodium hydroxide was added until the pH exceeded 12. After amine separation, this aqueous solution was extracted in methylene chloride (8 x 50 mL). After the organic layer that was obtained was dried using anhydrous sodium sulfate, it was concentrated, and pale yellow, oily 1,4,7-tri-n-octyl-1,4,7-triazacyclononane (2.45 g, 85% yield) was obtained.

4730-54-5, 4730-54-5 1,4,7-Triazacyclononane 188318, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; DIC Corporation; EP2269995; (2011); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

391604-55-0, 2-(2,4-Difluorophenyl)pyridine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

In a Schlenk’s flask equipped with a reflux condenser was placed (1,5-cyclooctadiene)iridium (I) chloride dimer (2.00 g, 2.98 mmol, 1 equivalent) and the interior of the flask was substituted with nitrogen. There were successively added 2-ethoxyethanol (20 mL, s/s=10) and 2-(2,4-difluorophenyl)pyridine (3.42 g, 17.88 mmol, 6.0 equivalents), and the mixture was stirred in a nitrogen atmosphere under refluxing (135C). Immediately after the addition of the ligand (2-(2,4-difluorophenyl)pyridine), the reddish suspension turned into gray and then into a dark reddish solution as the dissolution of the ligand by heating, which gave an lemon yellow suspension with stirring. After stirring for 3 hours, the solvent was distilled off from the reaction mixture under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol = 10/1). The column fractions were condensed, and the resulting yellow green solid material was recrystallized from hexane/dichloromethane to give 3. 53 g of the title compound (2-10) as yellow green powder in 97.4% yield. 1H NMR (500MHz CD2Cl2) : delta 5.29 (dd, J=2.5, 9.1 Hz, 4H), 6.38 (ddd, J=2.5, 9.1, 12.5Hz, 4H), 6.87 (ddd, J=1.5, 5.8, 7.2Hz, 4H), 7.87 (ddd, J=1.5, 5.8, 7.2Hz, 4H), 8.33 (ddd, J=0.7, 1.5, 8.1Hz, 4H), 9. 12 (ddd, J=0.7, 1.5, 5.8Hz, 4H).; Example 6 Production of Compound (3-10) (Bis[2-(2,4-difluorophenyl)pyridinato-N,C2′]iridium (III) acetylacetonate) (1) In a Schlenk’s flask equipped with a reflux condenser was placed (1,5-cyclooctadiene)iridium(I) chloride dimer (500 mg, 0.744 mmol, 1 equivalent) and the interior of the flask was substituted with nitrogen. There were successively added 2-ethoxyethanol (5 mL, s/s = 10) and 2-(2,4-difluorophenyl)pyridine (626 mg, 3.274 mmol, 4.4 equivalents), and the mixture was stirred in a nitrogen atmosphere under refluxing (135C) for 3 hours. The resulting lemon yellow suspension was cooled to room temperature, to which were added acetylacetone (230muL, 2.232 mmol, 3.0 equivalents) and sodium carbonate (237 mg, 2.232 mmol, 3.0 equivalents) successively, and further stirred under refluxing for 2 hours to give an yellow suspension. The solvent was distilled off from the reaction mixture under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane). The column fractions were condensed, and recrystallized from hexane/dichloromethane to give 896 mg of the title compound (3-10) as lemon yellow powder in 78.9%. 1H NMR (500MHz, CD2Cl2) : delta 1.80 (s, 6H), 5.31 (s, 1H), 5.50 (dd, J=2.4, 8.8Hz, 2H), 6.38 (ddd, J=2.4, 9.3, 12.5Hz, 2H), 7.24 (ddd, J=1.5, 5.7, 7.3Hz, 2H), 7.84 (ddt, J=0.6, 1.6, 7.3Hz, 2H), 8.22-8.28 (m, 2H), 8.44 (ddd, J=0.8, 1.6, 5.7Hz, 2H).; Example 10 Production of Compound (4-2) (Bis[2-(2,4-difluorophenyl)pyridinato-N,C6′]iridium (III) picolinate) In a Schlenk’s flask equipped with a reflux condenser was placed (1,5-cyclooctadiene)iridium (I) chloride dimer (500 mg, 0.744 mmol, 1.0 equivalent) and the interior of the flask was substituted with nitrogen. There were successively added 2-ethoxyethanol (5 ml, s/s=10) and 2-(2,4-difluorophenyl)pyridine (626 mg, 3.274 mmol, 4.4 equivalents), and the mixture was stirred in a nitrogen atmosphere under refluxing (135C) for 3 hours. The resulting lemon yellow suspension was cooled to room temperature, to which was added sodium picolinate (324 mg, 2.232 mmol, 3.0 equivalents), and further stirred under refluxing for 3 hours. The suspension slowly turn into orange with proceeding of the reaction. The solvent was distilled off from the reaction mixture under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol = 20/1). The column fractions were condensed, and the resulting yellow solid was recrystallized from hexane/dichloromethane to give 967 mg of the title compound (4-2) as lemon yellow powder in 93.6% yield. 1H NMR (500MHz CD2Cl2) delta 5.62 (dd, J=2.4, 8.7Hz, 1H), 5.85 (dd, J=2.4, 8.7Hz, 1H), 6.44 (ddd, J=2.4, 9.2, 12.6Hz, 1H), 6.50 (ddd, J=2.4, 9.2, 12.6Hz, 1H), 7.02 (ddd, J=1.5, 5.9, 7.4Hz, 1H), 7.21 (ddd, J=1.5, 5.9, 7.4Hz, 1H), 7.40 (ddd, J=1.5, 5.4, 7.6Hz, 1H), 7.46 (ddd, J=0.8, 1.6, 5.9Hz, 1H), 7.75-7.86 (m, 3H), 7.94 (dt, J=1.5, 7.6Hz, 1H), 8.20-8.28 (m, 2H), 8.28-8.37 (m, 1H), 8.69 (ddd, J=0.7, 1.6, 5.9Hz, 1H).; Example 12 Production of Compound (5-6) (tris [2-(2,4-difluorophenyl)pyridinato-N,C6′]iridium(III)) In a Schlenk’s flask equipped with a reflux condenser was placed (1,5-cyclooctadiene)iridium(I) chloride dimer (500 mg, 0.744 mmol, 1 equivalent) and the interior of the flask was substituted with nitrogen. There were successively added 2-ethoxyethanol (5 mL, s/s=10) and 2-(2,4-difluorophenyl)pyridine (626 mg, 3.274 mmol, 4.4 equivalents), and the mixture was stirred in a nitrogen atmosphere under refluxing (135C) for 3 hours. The resulting yellow green suspension was cooled to room temperature, to which w…

391604-55-0, As the paragraph descriping shows that 391604-55-0 is playing an increasingly important role.

Reference£º
Patent; TAKASAGO INTERNATIONAL CORPORATION; WO2004/43974; (2004); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33454-82-9,Lithium trifluoromethanesulfonate,as a common compound, the synthetic route is as follows.

General procedure: To the solution of 2-Cl (186 mg, 0.25 mmol) dissolvedin5.0 mL of methanol/CH2Cl2 (1/9), a 5% aqueous solution of sodiumtetrafluoroborate (1.5 g, 0.41 mmol) was added. The solution was stirredat room temperature for 1 h. Reaction was monitored by Alumina(Al2O3) TLC plate in MeOH/CH2Cl2 (5/95); an Rf ~ 0.9 of product washigher than Rf ~ 0.5 of 2-Cl. The organic layer was passed through ashort Al2O3 flash column. The crude product was collected after solventswere removed. The product isolated as fine off white powder was obtainedafter recrystallization from isopropanol/ethyl acetate. Yield 70%;, 33454-82-9

33454-82-9 Lithium trifluoromethanesulfonate 3664839, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Article; Wang, Ren-Tzong; Jane Tsai, Suh-Jen; Lee, Gene-Hsiang; Lai, Chung K.; Dyes and Pigments; vol. 173; (2020);,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

62937-45-5, D-Prolinamide is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,62937-45-5

C) (2R)-1-((1-(4-(4-methyl-1H-pyrazol-1-yl)pyridin-3-yl)piperidin-4-yl)carbonyl)pyrrolidine-2-carbonitrile (crude crystals) To a suspension of 1-(4-(4-methyl-1H-pyrazol-1-yl)pyridin-3-yl)piperidine-4-carboxylic acid (80 g) and acetonitrile (0.32 L) were added DIPEA (0.21 L), (R)-prolinamide (40 g) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (1.7M ethyl acetate solution, 0.28 L) at 0C. The mixture was stirred at room temperature for 1 hr, to the mixture was added 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (1.7M ethyl acetate solution, 0.35 L), and the mixture was stirred overnight at 70C. To the mixture was added saturated aqueous sodium hydrogen carbonate solution (1600 mL) at 0C, and the mixture was extracted with a mixed solvent of ethyl acetate and THF. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solution was purified by silica gel column chromatography (ethyl acetate). The solvent was evaporated under reduced pressure, to the residue was added diisopropyl ether, and the mixture was stirred overnight at room temperature. The solid was collected by filtration, and washed with diisopropyl ether to give the title compound (93 g). 1H NMR (300 MHz, DMSO-d6) 5 1.57-1.82 (4H, m), 1.89-2.30 (7H, m), 2.53-2.83 (3H, m), 2.86-3.06 (2H, m), 3.41-3.58 (1H, m), 3.62-3.75 (1H, m), 4.72 (1H, dd, J = 7.4, 4.0 Hz), 7.53 (1H, d, J = 5.3 Hz), 7.63 (1H, s), 8.31 (1H, d, J = 5.3 Hz), 8.41 (1H, s), 8.43 (1H, s).

62937-45-5 D-Prolinamide 447554, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; Takeda Pharmaceutical Company Limited; KOIKE, Tatsuki; KAJITA, Yuichi; YOSHIKAWA, Masato; IKEDA, Shuhei; KIMURA, Eiji; HASUI, Tomoaki; NISHI, Toshiya; FUKUDA, Hiromi; EP2933247; (2015); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

68737-65-5, (1R,2R)-N,N’-Dimethyl-1,2-cyclohexanediamine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 56 Preparation of N-(4-methylphenyl)benzamide using 4-chlorotoluene and N,N’-dimethyl-trans-1,2-cyclohexanediamine at 110 C. An oven-dried resealable Schlenk tube was charged with CuI (20 mg, 0.105 mmol, 5.1 mol %), benzamide (250 mg, 2.06 mmol), K2CO3 (600 mg, 4.34 mmol), evacuated and backfilled with argon. N,N’-Dimethyl-trans-1,2-cyclohexanediamine (35 muL, 0.222 mmol, 11 mol %) and 4-chlorotoluene (1.0 mL, 8.44 mmol) were added under argon. The Schlenk tube was sealed and the reaction mixture was stirred magnetically at 110 C. for 23 h. The resulting dark blue-green suspension was cooled to room temperature and filtered through a 0.5*1 cm pad of silica gel eluding with 10 mL of ethyl acetate. The light brown filtrate was concentrated and the residue was purified by flash chromatography on silica gel (2*20 cm; hexane-ethyl acetate 2:1; 15 mL fractions). Fractions 4-10 were concentrated, the solid residue was suspended in 10 mL of hexane and filtered to provide 392 mg (90% yield) of the product as fine white needles.

68737-65-5, 68737-65-5 (1R,2R)-N,N’-Dimethyl-1,2-cyclohexanediamine 2733821, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; Buchwald, Stephen L.; Klapars, Artis; Antilla, Jon C.; Job, Gabriel E.; Wolter, Martina; Kwong, Fuk Y.; Nordmann, Gero; Hennessy, Edward J.; US2003/65187; (2003); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

4730-54-5,With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4730-54-5,1,4,7-Triazacyclononane,as a common compound, the synthetic route is as follows.

General procedure: To a solution of 1,4,7-triazacyclononane (2 mmol) in distilled ethanol (50 mL) containing molecular sieve was added 1 equiv of aldehyde. The reaction mixture was stirred at room temperature. The solution was filtered and the filtrate was evaporated under reduced pressure to yield the aminal adduct.

The synthetic route of 4730-54-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Roger, Melissa; Patinec, Veronique; Bourgeois, Martine; Tripier, Raphael; Triki, Smail; Handel, Henri; Tetrahedron; vol. 68; 27-28; (2012); p. 5637 – 5643;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

54258-41-2, 1,10-Phenanthrolin-5-amine is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

54258-41-2, 5-Amino-1,10-phenanthroline (471 mg, 2.42 mmol) and 2,6-pyridinedicarbaldehyde (135 mg, 1 mmol) were refluxed in EtOH (20 mL) containing a catalytic amount of acetic acid for 6 h, giving a suspension. The reaction mixture was filtered hot, and the solid was washed with EtOH to afford the desired product as a yellow solid. Yield: 451 mg (92.2%). 1H NMR (300 MHz, CDCl3): delta = 7.48 (s, 2H), 7.65 (dd, J = 8.1, 4.5 Hz, 2H), 7.72 (dd, J = 8.4, 4.5 Hz, 2H), 8.14 (t, J = 7.5 Hz, 1H), 8.27 (d, J = 8.4 Hz, 2H), 8.57 (d, J = 7.5 Hz, 2H), 8.82 (d, J = 8.4 Hz, 2H), 8.96 (s, 2H), 9.17 (d, J = 3.9 Hz, 2H), 9.27 (d, J = 4.2 Hz, 2H). ESI-MS: m/z 490.4 (M+H)+, 512.4 (M+Na)+. IR numax (KBr, cm-1): 3399s (br), 1626s, 1593s, 1562m, 1501m, 1486m, 1453w, 1421s, 1385m, 1337w, 1298w, 1265w, 1209w, 1142w, 1061m, 993w, 977w, 941w, 866m, 799m, 738s, 679w, 626m, 526w, 458w, 412w.

54258-41-2 1,10-Phenanthrolin-5-amine 606970, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Article; Cheng, Feixiang; Ren, Mingli; He, Chixian; Yin, Hongju; Inorganica Chimica Acta; vol. 450; (2016); p. 170 – 175;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI