Day: June 17, 2021

Reference of 7598-35-8 ,Some common heterocyclic compound, 7598-35-8, molecular formula is C5H5BrN2, 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.

To a solution of 2-bromopyridin-4-amine (LVIII) (584 g, 3.38 mol, 1 eq) and sodium acetate (554 g, 6.75 mol, 2 eq) in HOAc (2000 mL) was added a solution of iodine monochloride (559 g, 3.44 mol, 176 mL, 1.02 eq) in HOAc (1000 mL) drop-wise at 70 C., the resulting mixture was stirred at 70 C. for 3 h. The mixture was concentrated to remove HOAc and poured into water (20 L). The aqueous solution was extracted with EtOAc (10 L*3). The combined organic layers were washed with saturated aq. Na2CO3 (20 L), saturated aq. Na2S2O3 (10 L), brine (10 L), dried over Na2SO4, filtered and concentrated to give a yellow residue, which was purified by column chromatography (1:1?1:0 petroleum ether:DCM) to obtain 2-bromo-5-iodopyridin-4-amine (II) as a yellow solid (340 g, 1.14 mol, 33.7% yield). H NMR (400 MHz, DMSO-d6) delta ppm 6.56-6.53 (3H, m), 7.73-7.72 (1H, d, J=5.2 Hz); ESIMS found for C5H4BrIN2 m/z 299.9 (M+1).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 7598-35-8, 2-Bromopyridin-4-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Mak, Chi Ching; Cao, Jianguo; Bollu, Venkataiah; Chiruta, Chandramouli; Mittapalli, Gopi Kumar; Eastman, Brian Walter; Hofilena, Brian Joseph; (960 pag.)US2019/127370; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 53014-84-9 , The common heterocyclic compound, 53014-84-9, name is 2-Methyl-5-formylpyridine, molecular formula is C7H7NO, 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 15 Preparation of 2-methyl-5-(oxiran-2-yl)py?dme [0380] The title compound was prepared by following general procedure 3 DMSO (4mL) was added to NaH 60% dispersion in oil (0 314 g, 7 8 mmol, 1 3 equiv ) and heated to 65 0C for 1 h THF (1OmL) was added at the same temperature and heated for another 10 mm After 10 mm , the reaction mixture was cooled to 00C T?methylsulfomum iodide (1 2 g, 5 9 mmol, 1 equiv ) was added and stirred for 10 mm and then a solution of 6-methylmcotmaldehyde (0 720 g, 5 9 mmol, 1 equiv ) in THF was added dropwise After complete addition, the reaction mixture was stirred at RT for 2 h, the product was detected by LCMS The reaction mixture was poured into ice water and the product was extracted in diethyl ether (4 x 5OmL), dried over Na2SO4 and concentrated at 25 0C to get the crude product 2-methyl-5-(oxiran-2-yl)py?dme (1 1 g crude)

The synthetic route of 53014-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; HUNG, David, T.; PROTTER, Andrew, Asher; JAIN, Rajendra, Parasmal; CHAKRAVARTY, Sarvajit; GIORGETTI, Marco; WO2010/51503; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 31181-53-0, 5-Fluoro-2-methylpyridine, 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, 31181-53-0, blongs to pyridine-derivatives compound. Computed Properties of C6H6FN

1 5-Fluoro-2-pyridinecarboxylic acid To water (100 ml) were added 5-fluoro-2-methylpyridine (J. Med. Chem., 32, 1970(1989): 2.2 g, 20 mmol) and potassium permanganate (19.1 g, 120 mmol), and heated under reflux for 4 hours. The reaction mixture was filtrated and the filtrate was concentrated, acidified with KHSO4, extracted with ethyl acetate and the extract was dried over Na2SO4. The sol vent was evaporated to give the title compound (0.80 g; 28%). 1H-NMR(270 MHz, DMSO-d6) 8.70 (d, J=2.8 Hz, 1H), 8.14 (dd, J=8.7, 4.6 Hz, 1H), 7.89 (td, J=8.7, 2.8 Hz, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,31181-53-0, its application will become more common.

Reference:
Patent; Sumitomo Pharmaceuticals Company, Limited; US6384033; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 1008-91-9, 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. 1008-91-9, name is 1-(Pyridin-4-yl)piperazine, molecular formula is C9H13N3, 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.

The crude material (1.15 g, 7.06 mmol) from Step B was dissolved in dichloromethane (50 mL). After addition of diisopropylethylamine (4.7 mL, 42.4 mmol), 3-nitrosalicylic acid (1.94 g, 10.6 mmol), and PyBrOP (5.78 g, 12.3 mmol), the resulting mixture was stirred over night at room temperature before being put into 1 N sodium hydroxide (300 mL). Extraction with dichloromethane (2?100 mL) removed all PyBrOP products. The aqueous phase was carefully acidified to pH 5-6 with 3N HCl and extracted with dichloromethane (3?100 mL). The combined organic layers of the neutral extraction were dried over sodium sulfate, concentrated, and finally purified by column chromatography (dichloromethane/methanol/NH4OH=10/1/0.1) to yield the desired product (850 mg, 37% for 2 steps).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1008-91-9, 1-(Pyridin-4-yl)piperazine.

Reference:
Patent; Schering Corporation; US2004/106794; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 13472-85-0, 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.13472-85-0, name is 5-Bromo-2-methoxypyridine, molecular formula is C6H6BrNO, molecular weight is 188.02, as common compound, the synthetic route is as follows.

To a solution of diisopropylamine (22.7 g, 0.22 mol) in THF (0.5L) was cooled to -30C, and then added n-BuLi (140 mL, 0.22 mol). After addition, the resulting solution was stirred for 0.5 h. The mixture was cooled to -60 C, Example 60a (35.1 g,0.19 mol) dissolved in THF (200 mL) was added dropwise,maintained the temperature below -60 C, the resulting solution was stirred for 1 h. DMF (20.4 g 0.28 mol) was added dropwise at -60 C, the resulting solution was stirred for 1 h .The reaction mixture was quenched by saturated NH4C1 (200 mL) aqueous, and allowed warmed to room temperature .the residue was extracted with EtOAc (200 mL * 2). The combined organic phase was washed with brine, dried over Na2S04, filtrated and concentrated under reduced pressure to give the crude product which was further purified by silica gel chromatography to give the pure product (Example 60b, 26.4 g, yield 64.3%) as a white solid. i NMR ^OO MHz, CDC13) delta 10.28 (s, 1H), 8.40 (s, 1H), 7.16 (s, 1H), 3.95 (s, 3H)

Statistics shows that 13472-85-0 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-methoxypyridine.

Reference:
Patent; FRONTHERA U.S. PHARMACEUTICALS LLC; JIN, Bohan; DONG, Qing; HUNG, Gene; (212 pag.)WO2017/218960; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 54923-31-8, 5-Bromo-6-methylpyridin-2-ol, 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, Product Details of 54923-31-8, blongs to pyridine-derivatives compound. Product Details of 54923-31-8

Step A: 5-Bromo-6-methyl-1-(2,2,2-trifluoroethyl)pyridin-2(1H)-one (0263) To a stirred mixture of 3-bromo-6-hydroxy-2-methylpyridine (25.0 g, 133 mmol) and cesium carbonate (52.0 g, 160 mmol) in 1,4-dioxane (600 mL) was added 2,2,2-trifluoroethyl triflate (40.1 g, 173 mmol) and the resulting mixture was heated at 50 C. for 4 h and then allowed to cool to ambient temperature. The resulting mixture was filtered and the filtrate was concentrated to dryness in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc-100:0 to 60:40, to give the title compound. MS: m/z=269.9 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,54923-31-8, 5-Bromo-6-methylpyridin-2-ol, and friends who are interested can also refer to it.

Reference:
Patent; Merck Sharp & Dohme Corp.; Bell, Ian M.; Fraley, Mark; Gallicchio, Steven N.; Ginnetti, Anthony; Mitchell, Helen J.; Paone, Daniel V.; Staas, Donnette D.; Wang, Cheng; Zartman, C. Blair; Stevenson, Heather E.; (30 pag.)US9499541; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 14248-50-1, 4-Bromopyridine 1-oxide, 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, 14248-50-1, blongs to pyridine-derivatives compound. COA of Formula: C5H4BrNO

Synthesis of Compound 26.5 [0251] To a mixture of 26.4 (2.6 g, 7.5 mmol, 1.0 eq) and 4-bromopyridine 1-oxide (1.3 g, 7.5 mmol, 1.0 eq) in DCM (150 mL), PyBrop (4.6 g, 9.5 mmol, 1.3 eq) and DIPEA (3.9 g, 30.1 mmol, 4.0 eq) were added. The mixture was stirred at room temperature for 12 h. The mixture was washed with water (50 mL x 2). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column (PE / EA = 2 / 1) to give 26.5 (1.6 g, yield: 42%) as a yellow oil. 1H NMR (400 MHz, CDC13) delta: 7.89-7.86 (m, 2H), 7.56-7.54 (m, 1H), 6.98 (d, J = 8.8 Hz, 1H), 6.69 (dd, J = 1.6, 5.6 Hz, 1H), 6.56 (d, J = 1.6 Hz, 1H), 4.75-4.72 (m, 1H), 4.11 (t, J = 6.0 Hz, 2H), 3.46 (s, 2H), 3.30- 3.25 (m, 2H), 2.60-2.53 (m, 4H), 1.19-1.84 (m, 2H), 1.70-1.60 (m, 8H), 1.51-1.41 (m, 2H); ESI-MS (M+H)+: 503.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14248-50-1, its application will become more common.

Reference:
Patent; BIOGEN IDEC MA INC.; JENKINS, Tracy; VESSELS, Jeffery; WO2014/143672; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 5654-95-5, 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.5654-95-5, name is 1H-Pyrrolo[2,3-b]pyridine-2,3-dione, molecular formula is C7H4N2O2, molecular weight is 148.1189, as common compound, the synthetic route is as follows.

To a THF solution of E1 and RI-Br (R1 = alpha-methyl-p-fluorobenzyl) will be added NaH (1.1 eq) and the solution will be heated until the starting material disappears. After removal of volatiles, the residue will be chromatographed to give compound E2.

Statistics shows that 5654-95-5 is playing an increasingly important role. we look forward to future research findings about 1H-Pyrrolo[2,3-b]pyridine-2,3-dione.

Reference:
Patent; SCHERING CORPORATION; WO2009/20580; (2009); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 1211530-54-9, 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.1211530-54-9, name is 5-(Bromomethyl)nicotinonitrile, molecular formula is C7H5BrN2, molecular weight is 197.03, as common compound, the synthetic route is as follows.

To a solution of 5-chloro-2-hydroxy-4-(4-phenylindan-1-yl)oxy-benzaldehyde (100 mg, 0.274 mmol) in DMF (5 mL) was added 5-(bromomethyl)pyridine-3-carbonitrile (108 mg, 0.549 mmol) followed by Cs2CO3 (178 mg, 0.549 mmol). The resulting suspension was then stirred at 65 C. for 2 h. The reaction mixture was diluted with EtOAc (20 mL),washed with water (20 mL), dried (MgSO4), concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 80% EtOAc in hexanes) to obtain 5-[[4-chloro-2-formyl-5-(4-phenylindan-1-yl)oxy-phenoxy]methyl]pyridine-3-carbonitrile. MS: (ES) m/z calculated for C29H22ClN2O3[M+H]+ 481.1. found 481.3.

Statistics shows that 1211530-54-9 is playing an increasingly important role. we look forward to future research findings about 5-(Bromomethyl)nicotinonitrile.

Reference:
Patent; CHEMOCENTRYX, INC.; LANGE, Christopher; MALATHONG, Viengkham; McMURTRIE, Darren J.; PUNNA, Sreenivas; SINGH, Rajinder; YANG, Ju; ZHANG, Penglie; (210 pag.)US2018/8554; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 73290-22-9, 2-Bromo-5-iodopyridine, 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, Computed Properties of C5H3BrIN, blongs to pyridine-derivatives compound. Computed Properties of C5H3BrIN

To a solution of 2-bromo-5-iodopyridine (1.00 g, 3.52 mmol), tert-butyl (R)-(3H- spiro[benzofuran-2,4′-piperidin]-3-yl)carbamate (1.09 g, 3.52 mmol, Intermediate EB) and Cs2C03 (3.44 g, 10.6 mmol) in toluene (10.0 mL) was added XantPhos-Pd-G4 (339 mg, 352 umol). The mixture was stirred at 80 C for 12 h. The mixture was then filtered and the filtrate was concentrated under reduced pressure to give a residue. The residue was purified by Pre-HPLC (column: Phenomenex Synergi C18 250*50*l0um; mobile phase: [water (0.05%ammonia hydroxide v/v)-ACN]; B%: 46%-7l%, 36min, 80%min) to give (R)-N- ((R)-r-(6-bromopyridin-3-yl)-3H-spiro[benzofuran-2,4′-piperidin]-3-yl)-2-methylpropane-2- sulfmamide (570 mg, 1.23 mmol, 35% yield) as a white solid. LC-MS (ESI+) m/z 466.1 (M+H)+; 1HNMR (400 MHz, CDCl3): d 8.04 (d, J = 3.20 Hz, 1H), 7.31-7.29 (m, 3H), 7.14-7.11 (m, 1H ), 7.56-7.53 (m, 2H), 6.96-6.95 (m, 1H), 6.85 (d, J = 8.00 Hz, 1H), 4.73 (d, J = 10.8 Hz, 1H), 3.72 (d, J = 10.8 Hz, 1H), 3.66-3.53 (m, 2H), 3.26-3.22 (m, 2H), 2.28-2.16 (m, 1H), 2.16-2.13 (m, 1H), 1.96-1.83 (m, 2H), 1.28 (s, 9H).

The synthetic route of 73290-22-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RELAY THERAPEUTICS, INC.; D.E. SHAW RESEARCH, LLC; TAYLOR, Alexander, M.; LESCARBEAU, Andre; KELLEY, Elizabeth, H.; SHORTSLEEVES, Kelley, C.; WALTERS, W., Patrick; MURCKO, Mark, Andrew; MCLEAN, Thomas, H.; GUNAYDIN, Hakan; GIORDANETTO, Fabrizio; THERRIEN, Eric; (607 pag.)WO2019/183367; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem