Day: March 18, 2022

Reference of 138891-51-7 ,Some common heterocyclic compound, 138891-51-7, molecular formula is C8H6N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

EXAMPLE 11[2-(6-chloropyridin-3-yl)-4-(2-methoxyethoxy)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)- yl] (imidazo [1,5 -ajpyridin- 1 -yl)methanone (Q-2) O-l (2 g, 6.23 mmol), imidazo[l,5-a]pyridine-l-carboxylic acid (Q-I, 1.112 g,6.86 mmol), EDC (1.315 g, 6.86 mmol), HOBt (0.907 g, 5.92 mmol), and TEA (2.61 mL, 18.70 mmol) were combined in DMF (31 mL) and heated to 60 ºC for 1 hr. Imidazo[l,5-a]pyridine-l- carboxylic acid was prepared according to the literature procedure: Kolar, P.; Petric, A.; Tisler, M.; Felluga, F. J. Heterocycl. Chem. 1991, 7, 1715-1720. The mixture was diluted with EtOAc (100 mL) and washed with sat. aq. NaHCO3 (100 mL), water (100 mL), and brine (100 mL). The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by gradient elution on silica gel (0 to 45% [10% MeOH in DCM] in DCM over 50 min to afford the title compound as a white solid (2.43 g, 84%). Data for Q-2: 1H NMR (500 MHz, CDCl3) delta 9.35 (s, IH), 8.61 (d, J= 8.3 Hz, IH), 8.26 (d, J= 9.3 Hz, IH), 8.07 (s, IH), 8.01 (d, J= 6.8 Hz, IH), 7.39 (d, J= 8.3 Hz, IH), 7.03 (t, J= 7.8 Hz, IH), 6.76 (t, J= 6.8 Hz, IH), 4.41-5.60 (vbm, 4H), 4.65 (bs, 2H), 3.81 (bs, 2H), 3.46 (s, 3H), 3.13 (bs, 2H); HRMS m/z (M+H) 465.1426 found, 465.1436 required.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,138891-51-7, its application will become more common.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; BRESLIN, Michael, J.; COLEMAN, Paul, J.; COX, Christopher, D.; RAHEEM, Izzat, T.; SCHREIER, John, D.; WO2010/138430; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 100202-78-6, name is 2-(Bromomethyl)-6-fluoropyridine, molecular formula is C6H5BrFN, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Quality Control of 2-(Bromomethyl)-6-fluoropyridine

General procedure: Hexamethylenetetramine (159 mg, 1.13 mmol, 1.0 eq.) was added under stirring to a solution of 10-6a or 10-6b (1.0 eq.) in chloroform (15 mL). The resulting mixture was stirred at 50C for 1 hour. After cooling to rt, the solvent was removed under reduced pressure. The residue was dissolved with ethanol (10 mL) and concentrated hydrochloric acid (0.5 mL) was added. This mixture was stirred at 50C for 2 hours and at room temperature overnight. The solvent was then evaporated under reduced pressure to give the desired crude products 10a (white solid) or 10b (yellow solid) which were used in the next step without further purification.

With the rapid development of chemical substances, we look forward to future research findings about 100202-78-6.

Reference:
Article; Wenzel, Barbara; Liu, Jianrong; Dukic-Stefanovic, Sladjana; Deuther-Conrad, Winnie; Teodoro, Rodrigo; Ludwig, Friedrich-Alexander; Chezal, Jean-Michel; Moreau, Emmanuel; Brust, Peter; Maisonial-Besset, Aurelie; Bioorganic Chemistry; vol. 86; (2019); p. 346 – 362;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56673-34-8, 3-Bromo-6-mercaptopyridine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, name: 3-Bromo-6-mercaptopyridine, blongs to pyridine-derivatives compound. name: 3-Bromo-6-mercaptopyridine

Powdered sodium methoxide (1.08 g, 19.95 mmol) and 1-bromo-3-chloropropane (2.87 mL, 28.7 mmol) were added to a stirred suspension of 5-bromopyridine-2-thiol (3.16 g, 16.63 mmol) in anhydrous methanol (80 mL). The mixture was heated at 60C and stirred under N2 for 1.5 h. After cooling to room temperature, the mixture wasquenched with water-brine (1:1, 100 mL) and extracted with EtOAc (2 x 100 mL). The combined organic fraction was washed with brine (50 mL), then dried (MgSO4) and reduced in vacuo, to give the title compound (3.92 g, 88%) as a yellow solid. H (500 MHz, CDC13) 8.50-8.44 (m, 1H), 7.58 (dd,J8.5, 2.4 Hz, 1H), 7.07 (dd,J8.5, 0.6 Hz, 1H), 3.67 (t,J6.4 Hz, 2H), 3.29 (t,J6.9 Hz, 2H), 2.17 (p,J6.6 Hz, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,56673-34-8, 3-Bromo-6-mercaptopyridine, and friends who are interested can also refer to it.

Reference:
Patent; UCB BIOPHARMA SPRL; ALEXANDER, Rikki Peter; BENTLEY, Jonathan Mark; BRACE, Gareth Neil; BROOKINGS, Daniel Christopher; CHOVATIA, Praful Tulshi; DEBOVES, Herve Jean Claude; JOHNSTONE, Craig; JONES, Elizabeth Pearl; KROEPLIEN, Boris; LECOMTE, Fabien Claude; MADDEN, James; MILLER, Craig Adrian; PORTER, John Robert; SELBY, Matthew Duncan; SHAW, Michael Alan; VAIDYA, Darshan Gunvant; YULE, Ian Andrew; WO2015/86506; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 22280-60-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 22280-60-0, name is 6-Chloro-2-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

Step 1: 6-Chloro-2-methylpyridin-3-amine (44). To a stirred solution of 43 (5 g, 29 mmol) in EtOH (20 mL) and cone. HCI (20 mL) was added Fe powder (16.2 g, 289 mmole) in small portions at RT over 30 min. Stirring was continued at RT for another 30 min. The solvent was distilled off under reduced pressure. Water was added and the resulting mixture was neutralized with NaHC03. EtOAc was added and the biphasic mixture was filtered through Celite and washed with EtOAc. The phases of the filtrate were separated and the organic layer was washed with water, brine, dried over Na2S04, and concentrated to afford 44 (4.1 g, 99 %) as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,22280-60-0, 6-Chloro-2-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; EXELIXIS, INC.; XU, Wei; (106 pag.)WO2017/4608; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 14121-36-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 14121-36-9, name is 2,3,4,6-Tetrachloropyridine, molecular formula is C5HCl4N, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Step 1: 100g of tetrachloropyridine, 0.5g of catalyst, 15g of acid binding agent,3g of auxiliary agent and 500g of organic solvent are placed in a 1L autoclave, and the autoclave is evacuated three times until the autoclave is in a vacuum state;The tetrachloropyridine is 2,3,4,6-tetrachloropyridine;The catalyst includes a supported activated carbon, a metal M1, a metal M2, and a metal M3 supported on the supported activated carbon,The metal M1 is Pd, the metal M2 is Ag, and the metal M3 is V,The mass percentage content of metal M1 in the catalyst is 2%, and the mass percentage content of metal M2 is 0.4%.The mass percentage of metal M3 is 0.15%; The acid binding agent is triethylamine and urea, and the mass ratio of the triethylamine and urea is 1: 1;The auxiliary is citric acid;The organic solvent is ethyl acetate; Step 2: Replace the high-pressure reactor after vacuuming in Step 1 with nitrogen for three times, and then replace with hydrogen for three times;Step three, continue to introduce hydrogen into the autoclave after the hydrogen replacement in step two, control the hydrogen pressure to 1.0 MPa, the temperature to 50 C., and react for 7 hours under the stirring condition, and reduce to room temperature;Step 4: Drain the hydrogen in the autoclave after the temperature drops to room temperature in Step 3, replace it with nitrogen for three times, filter the system in the autoclave to obtain the filtrate and the recovered catalyst, and reuse the recovered catalyst; Step 5. Distillate the filtrate in step 4 under reduced pressure to obtain 2,3-dichloropyridine as a white solid.The solvent obtained by vacuum distillation is recovered and reused; the vacuum of the vacuum distillation is -0.092 MPaThe temperature of the vacuum distillation was 40 C. The yield of 2,3-dichloropyridine was 98.1%, and the purity was 99.3%.

According to the analysis of related databases, 14121-36-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Xi’an Kaili New Materials Co., Ltd.; Li Xiaoan; Xiao Dawei; Han Bin; Zhang Yu; Zhang Zhixiang; Zeng Yongkang; Wan Kerou; Gao Wu; (13 pag.)CN110759859; (2020); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13269-19-7, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 13269-19-7, name is 2-Nitropyridin-3-amine. A new synthetic method of this compound is introduced below.

General procedure: choloro acetylcholoride (24mmol) and Et3N (24mmol) was added to a solution of 2-chloro-3-aminopyridine 7e (20mmol) in CH2Cl2 (20mL) at room temperature. The mixture was stirred for 5 hrs, and the solvent was evaporated under vacuum. The residue was purified by column chromatography (CH2Cl2:CH3OH: 30:1) on silica gel to obtain pure compound 8e as a white powder in 72% yield. To a solution of amide derivative 8e (5mmol) and potassium carbonate (7.5mmol) in acetonitrile (20ml) was added isothiocyanate (6mmol) during about 5min. The reaction mixture was stirred at room temperature overnight, and the solvent was evaporated under vacuum. The residue was extracted with ethyl acetate (20mL×3). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The obtained residue was purified by silica gel flash chromatography column (CH2Cl2:CH3OH: 30:1) to afford 5l as a white solid in 82% yield. To a solution of 5l (1mmol) in glacial acetic acid (5mL) were added aldehyde 6b (1mmol) and beta-alanine (1mmol). The resulting mixture was stirred under reflux for 2h. Upon completion of the reaction, the mixture was cooled, the reaction was quenched with water, and the precipitate was filtered off, then the residue was purified by column chromatography (CH2Cl2:CH3OH: 15:1) on silica gel to obtain pure compound 2r as a faint yellow powder in 80% yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,13269-19-7, its application will become more common.

Reference:
Article; Cai, Ming-Guang; Wu, Yang; Chang, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 10; (2016); p. 2517 – 2520;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 886365-06-6, name is Methyl 5-bromo-4-methylpicolinate, molecular formula is C8H8BrNO2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. Computed Properties of C8H8BrNO2

Step 1 To a solution of 5-bromo-4-methylpyridine-2-carboxylic acid methyl ester (2.207 g, 9.59 mmol), 4-methoxylphenylboronic acid (1.604 g, 10.55 mmol) and 1,1′-bis(di-tert-butylphosphino)ferrocene palladium dichloride (0.313 g, 0.480 mmol) in THF (30 mL) was added potassium carbonate (2.0 M in water, 10.1 mL, 20.15 mmol). The mixture was purged with nitrogen and heated at 50 C. for 1 hour and at 60 C. for 5 hours. The reaction was poured into ethyl acetate and was washed with brine, dried over sodium sulfate, filtered and concentrated. It was purified by column chromatography to yield methyl 5-(4-methoxyphenyl)-4-methylpyridine-2-carboxylate (2.47 g, 9.59 mmol) as a pink solid. MS ESI calc’d. for C15H16NO3 [M+H]+ 258.1. found 258.1.

With the rapid development of chemical substances, we look forward to future research findings about 886365-06-6.

Reference:
Patent; Shao, Pengcheng Patrick; Sun, Wanying; Katipally, Revathi Reddy; Vachal, Petr; Ye, Feng; Liu, Jian; Sha, Deyou; US2013/109649; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 182181-42-6, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.182181-42-6, name is 2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine, molecular formula is C9H9ClN2, molecular weight is 180.63, as common compound, the synthetic route is as follows.

EXAMPLE 55 2-[[4-(2,4-Dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine monomaleic acid salt. Refer to Chart E A mixture of 2-(chloromethyl)-8-methylimidazo[1,2-a]pyridine (Example 54, Step 1; 0.294 g), 1-(2,4-dichlorophenyl)piperazine (Example 31, Step 1; 0.396 g) diisopropylethylamine (0.35 mL), and THF (2 mL) is heated at 75 C. for 5 hours. The mixture is then concentrated under reduced pressure, partitioned between saturated aq. sodium bicarbonate and dichloromethane, and the combined organic layers are dried with MgSO4 and concentrated under reduced pressure. The residue is chromatographed on silica gel using methanol/dichloromethane (4/96) and the appropriate fractions are combined and concentrated to give 2-[[4-(2,4-dichlorophenyl)-1-piperazinyl]methyl]-8-methylimidazo[1,2-a]pyridine.

Statistics shows that 182181-42-6 is playing an increasingly important role. we look forward to future research findings about 2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine.

Reference:
Patent; Pharmacia & Upjohn Company; US5912246; (1999); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 790692-90-9, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 790692-90-9, name is 6-Chloro-5-iodo-3-nitropyridin-2-amine. A new synthetic method of this compound is introduced below.

The compound 268-100 was prepared as follows. To a solution of 6-chloro-3-nitropyridin-2-amine (630 mg, 3.63 mmol) in ethanol (11 mL) was add I2 (920 mg, 3.62 mmol) and Ag2SO4 (1132 mg, 3.63 mmol).). The resulting solution was stirred overnight at room temperature and dissolved in water (100 mL), then extracted with ethyl acetate (3×80 ml). The combined organic layers were washed with brine (50 ml), dried over anhydrous sodium sulfate and concentrated under vacuum to produce 6-chloro-5-iodo-3-nitropyridin-2-amine as a yellow solid (640 mg, 59%). Next, to a solution of 6-chloro-5-iodo-3-nitropyridin-2-amine (640 mg, 2.14 mmol) in ethanol (40 ml) and water (10 ml) was added Fe powder (1.93 g, 34.46 mmol) and NH4Cl (887 mg, 16.58 mmol). The resulting solution was heated to reflux for 4 h and then concentrated. The residue was dissolved in water (100 mL) and extracted with ethyl acetate (3×80 ml). The combined organic layers was washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 33% ethyl acetate in petroleum ether to produce 6-chloro-5-iodopyridine-2,3-diamine as a brown solid (560 mg, 97%). The mixture of 6-chloro-5-iodopyridine-2,3-diamine (100 mg, 0.37 mmol), (2,3-dichlorophenyl)boronic acid (147.3 mg, 0.77 mmol), Pd(Ph3P)4 (42.9 mg, 0.04 mmol) and sodium carbonate (118.2 mg, 1.12 mmol) in water (5 mL) and dioxane (15 mL) was heated to reflux overnight. Then the resulting solution was quenched with water (100 mL) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column with 50% ethyl acetate in petroleum ether to produce 6-chloro-5-(2,3-dichlorophenyl)pyridine-2,3-diamine as a brown solid (80 mg, 75%). Finally, the solution of 6-chloro-5-(2,3-dichlorophenyl)pyridine-2,3-diamine (80 mg, 0.28 mmol) in trifluoroacetic acid (10 mL) and hydrochloric acid (conc., 2 mL) was heated to reflux overnight. Then the resulting mixture was quenched with water (100 mL), adjusted pH to 8 with sodium carbonate and extracted with ethyl acetate (3×80 mL). The combined organic layers was dried over anhydrous magnesium sulfate and concentrated to give a residue, which was purified by a silica gel column with 50% ethyl acetate in petroleum ether to produce 5-chloro-6-(2,3-dichlorophenyl)-2-(trifluoromethyl)-1H-imidazo[4,5-b]pyridine. Trifluoroacetic acid as a off-white solid (2 mg, 2%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,790692-90-9, its application will become more common.

Reference:
Patent; MERIAL LIMITED; Meng, Charles Q.; US2013/281392; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 914942-88-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 914942-88-4, name is tert-Butyl (6-amino-7-iodo-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl)(methyl)carbamate, molecular formula is C13H18IN5O2, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Al.12 (0.3g, 0.74 mm ol), pyruvic acid (98mg, 1.12mmol), triethylamine and palladium dibenzylidene acetone (68mg, 0.074mmol) in dry DMF (3mL) were heated to 120C for 15 min in a microwave. The reaction mixture was diluted with water (3 mL) and extracted with ethyl acetate (10 niL). The organic extract was discarded and the aqueous layer acidified to pH 3-4 using IN HCL The acidified aqueous layer was then extracted with ethyl acetate (3 x 20 mL), the combined organics dried (MgSO4) and evaporated in vacuo to give A168.1 (lbetalmg, 62%). HPLC YMC S-5 4.6x33mm EPO W(2min grad): retention time 1.32min, M+H+ = 346.31, NMR (400MHz, DMSO) delta 12.49 (s, IH), 8.16 (s, IH), 7.47 (s, IH), 4.04 (s, 3H), 3.29 (s, 3H), 1.30 (s, 9H).

According to the analysis of related databases, 914942-88-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2006/122137; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem