Tag: M.W:200-300

Synthetic Route of 83004-10-8 ,Some common heterocyclic compound, 83004-10-8, molecular formula is C6H5Br2N, 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.

Synthesis of N-((6-Bromopyridin-2-yI)methyl)-N-(1-isopropylpiperidin-4-yI)-4-(4-(trifluoromethyl)phenyl)pyrimidin-2-amineTo an ice-cooled solution of (1 -isopropyl-piperid in-4-yl)-[4-(4-trifluoromethyl-phenyl)-pyrimidin-2-yl]-amine (1.00 g, 2.74 mmol, 1.0 eq.) in DMF (15 mL), sodium hydride 60%dispersion in mineral oil (154 mg, 3.84 mmol, 1.4 eq.) was added. The resulting orange mixture was stirred at r.t. for 2 hours. Then a solution of 2-bromo-6-(bromomethyl)pyridine (757 mg, 3.02 mmol, 1.1 eq.) in DMF (5 mL) was added dropwise and the mixture was stirred at 60 C for 18 hours. The mixture was cooled to 0 C and sodium hydride 60%dispersion in mineral oil (77 mg, 1.92 mmol, 0.7 eq.) was added. The resulting orange mixture was stirred at r.t. for 2 hours. Then a solution of 2-bromo-6-(bromomethyl)pyridine (378 mg, 1.51 mmol, 0.55 eq.) in DMF (2 mL) was added dropwise and the mixture was stirred at 60 C 4 hours. The reaction mixture was quenched with sat. aq. Na2CO3 solution. The mixture was extracted with DCM. The comb. org. phases were washed with water, sat.aq. NaCI soln., dried over MgSO4, and concentrated in vacuo. The residue was purified by flashmaster (column: 50 g, flow: 40 mL/min, 35 fractions of 45 mL, Hept/AcOEt-NEt3 (10% NEt3) 95:5 to Hept/AcOEt-NEt3 (10% NEt3) 1:1) to afford the title compound as an orange oil.LC-MS 4: tR = 0.82 mm; [M+H] = 534.2

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. 83004-10-8, 2-Bromo-6-(bromomethyl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; AISSAOUI, Hamed; BOSS, Christoph; CIANA, Claire-Lise; KIMMERLIN, Thierry; SIEGRIST, Romain; WO2015/28989; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1256823-65-0 ,Some common heterocyclic compound, 1256823-65-0, molecular formula is C6H2BrClN2, 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 mixture of 5-bromo-6-chloropicolinonitrile (5 g, 22.99 mmol) and tributyl (1-ethoxyvinyl) stannane (8.30 g, 22.99 mmol) in toluene (10 mL) was added tetrakis (triphenyl-phosphine) palladium (0) (0.531 g, 0.460 mmol) and the mixture was stirred at 110 under N2for 16h. The mixture was cooled to rt and conc. HCl (1.888 mL, 22.99 mmol) was added to the mixture. The grey mixture was stirred at 25 for 1h. The mixture was diluted with water (10 mL) and extracted with ethyl acetate (15 mL x 3) . The combined organic layers were washed with brine (10 mL x 2) , dried over sodium sulfate, filtered and the filtrate was concentrated in vacuum. The residue was purified by column chromatography (SiO2, petroleum ether: ethyl acetate from 10: 1 to 3: 1) to give the title compound.1HNMR (CDCl3, 400 MHz) delta: 7.99 (d, J 8.0 Hz, 1H) , 7.73 (d, J 7.6 Hz, 1H) , 2.72 (s, 3H) .

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. 1256823-65-0, 5-Bromo-6-chloropicolinonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MSD R&D (CHINA) CO., LTD.; BAO, Jianming; HENDERSON, Timothy J.; LO, Michael Man-chu; MAZZOLA, JR., Robert D.; RUDD, Michael T.; TELLERS, David M.; TONG, Ling; LI, Chunsing; NA, Meng; (144 pag.)WO2019/238; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 59786-31-1 ,Some common heterocyclic compound, 59786-31-1, molecular formula is C7H6BrNO2, 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.

Compound 115a. To a solution of methyl 3-bromoisonicotinate (0.2 g, 0.93 mmol, 1.0 equiv) in Dioxane (10 mL) was added benzenethiol (0.204 g, 1.85 mmol, 2.0 equiv), KOAc (0.184 g, 1.876 mmol, 2.0 equiv) and resulting reaction mixture purged with N2 gas for 10 minute, followed by the addition of Pd2(dba)3 (0.042 g, 0.046 mmol. 0.05 equiv), Xanthphose (0.026 g, 0.046 mmol, 0.05 equiv) and resulting reaction mixture). The resulting reaction mixture was heated at 90 C. for overnight. Product formation was confirmed by LCMS. After the completion of reaction, the mixture was filtered through celite bed, washed with ethyl acetate (100 mL). Filtrate was concentrated under reduced pressure. The crude product obtained was purified by flash chromatography (20% ethyl acetate hexane as an eluent) to obtain methyl 3-(phenylthio)isonicotinate (0.100 g, 44.4% Yield) as yellow oil. (0939) LCMS 246.1 [M+H]+ (0940) 1H NMR (400 MHz, DMSO-d6) delta 8.92 (br. s., 1H), 8.76-8.56 (m, 2H), 7.50 (s, 1H), 7.48-7.40 (m, 2H), 7.40-7.29 (m, 2H), 5.14-5.04 (m, 1H), 4.21 (br. s., 1H), 4.03 (d, J=2.6 Hz, 2H), 2.87 (br. s., 1H), 2.79 (d, J=14.5 Hz, 1H), 2.67 (br. s., 1H).

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. 59786-31-1, Methyl 3-bromoisonicotinate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Praxis Biotech LLC; ALFARO, Jennifer; BELMAR, Sebastian; BERNALES, Sebastian; PUJALA, Brahmam; PANPATIL, Dayanand; BHATT, Bhawana; US2019/185451; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 884495-14-1 ,Some common heterocyclic compound, 884495-14-1, molecular formula is C7H7BrN2O3, 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.

DMF-DMA (600 mL) was slowly added to a stirred and heated (80 C) solution of 5-bromo-2- methoxy-4-methyl-3-nitropyridine (134 g, 0.54 mol) in DMF (1.1 L). After addition, the mixture was heated at 95 C for 5 h, at which time TLC indicated the reaction had gone to completion. The mixture was cooled to room temperature and poured into ice-cold water (3 L). The resulting red solid was collected by filtration, washed with water, and dried under reduced pressure to give the title compound (167 g, 100% yield) as red solid. 1H NMR (400 MHz, DMSO-d6): 6 8.24 (s, 1 H), 7.05 (d, J= 13.6 Hz, I H), 7.05 (d, J= 13.6 Hz, 1 H), 4.80 (d, J = 13.2 Hz, 1 H), 3.88 (s, 3 H), 2.90 (s, 6 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,884495-14-1, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; BELLON, Steven, F.; BURDICK, Daniel, J.; COTE, Alexandre; CRAWFORD, Terry; DAKIN, Les, A.; HEWITT, Michael, Charles; HSIAO-WEI TSUI, Vickie; LEBLANC, Yves; MAGNUSON, Steven, R.; NASVESCHUK, Christopher, G.; ROMERO, F. Anthony; TANG, Yong; TAYLOR, Alexander, M.; WANG, Shumei; (128 pag.)WO2016/77380; (2016); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.53636-56-9, name is Methyl 3-bromo-2-pyridinecarboxylate, molecular formula is C7H6BrNO2, molecular weight is 216.03, as common compound, the synthetic route is as follows.COA of Formula: C7H6BrNO2

N-((4-chloro-2-methylphenyl)(phenyl)methyl)-2-(2-(2-(hydroxymethyl)pyridin-3-yl)benzofuran-5- yl)acetamidea) (3-bromopyridin-2-yl)methanolTo a solution of methyl 3-bromopicolinate (1 g, 4.6 mmol) in MeOH (50 mL) at 0 C was added NaBH4 (883 mg, 23.2 mmol). The reaction mixture was stirred at rt overnight, followed by concentration under reduced pressure. The resultant residue was dissolved in EtOAc (50 mL), washed with aq. NH4C1 (3 x 20 mL), dried over Na2S04, filtered, and concentrated to afford the title compound (101 g, 92%) as a white solid. LCMS-P 1 : 190/192 [M+H]+; Rt: 1.070 min

At the same time, in my other blogs, there are other synthetic methods of this type of compound,53636-56-9, Methyl 3-bromo-2-pyridinecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; BOHNERT, Gary, J.; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; SUNG, Leonard; WO2013/19682; (2013); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 66572-56-3 ,Some common heterocyclic compound, 66572-56-3, molecular formula is C6H4BrNO2, 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.

Preparation of Example 4 (S)-N-((S)-Cyclohexyl-2-{(S)-2-{2-[2,3-dihydro-indol-1-yl)-pyridin-4-yl]-pyrrolidin-1-yl}-pyrrolidin-1-yl)-2-oxo-ethyl)-2-methylamino-propionamide 2-Bromo-N-methoxy-N-methyl-isonicotinamide (1)To a solution of 2-bromo-pyridine-4-carboxylic acid (11.83 g, 58.56 mmol) in DMSO (100 mL) are added HOBt (9.49 g, 70.30 mmol) and HBTU (26.70 g, 70.30 mmol). The mixture is stirred at room temperature for 20 min, then N,O-dimethylhydroxylamine HCl (6.28 g, 64.41 mmol) and diisopropylethylamine (22.72 g, 175.68 mmol) are added to the mixture. After stirring at room temperature for 3 h, the reaction mixture is diluted with water and extracted with EtOAc. The combined organic layers are washed with water, sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated down. The crude product is purified by flash chromatography on silica gel (EtOAc/Hexane: 10%40%) to give 2-Bromo-N-methoxy-N-methyl-isonicotinamide (12.4 g, 86%) as a white solid. M/Z=245.0

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,66572-56-3, its application will become more common.

Reference:
Patent; Novartis AG; US2011/15232; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 178876-86-3, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 178876-86-3, name is Methyl 5-bromo-6-oxo-1,6-dihydropyridine-2-carboxylate. This compound has unique chemical properties. The synthetic route is as follows.

Pd(PPh3)2C12 (30 mg, 0.0424 mmol) was added to a nitrogen flushed mixture of methyl 5- bromo-6-oxo- 1 ,6-dihydropyridine-2-carboxylate (98.4 mg, 0.424 mmo 1), 4- isopropylphenylacetylene (92 mg, 0.636 mmol), Cul (16.1 mg, 0.0848 mmol) and Et3N (600 jil) in THF (1.5 ml) and the mixture was heated at 100 C in microwave reactor for 15 mm. Solvent evaporated and residue purified by flash chromatography using 20-33% EtOAc aseluent. Yield: 55.5 mg (44%); beige solid.

According to the analysis of related databases, 178876-86-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KANCERA AB; HAMMER, Kristin; JOeNSSON, Mattias; KRUeGER, Lars; (230 pag.)WO2017/108282; (2017); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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.136888-26-1, name is 5,6-Dichloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one, molecular formula is C7H4Cl2N2O, molecular weight is 203.0255, as common compound, the synthetic route is as follows.Recommanded Product: 5,6-Dichloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one

Example 51 5,6-Dichloro-3-(2-furoyl)-4-azaoxindole-1-N-t-butyl carboxamide 5,6-Dichloro-3-(2-furoyl)-4-azaoxindole was first prepared according to the procedure of Example 1B, using 5,6-dichloro-4-azaoxindole (763 mg, 3.76 mmol), sodium (0.43 g, 18.8 mmol), ethyl-2-furoate (1.05 g, 7.5 mmol) and ethanol (25 mL). Yield: 0.98 g (88%). The title compound was prepared from 5,6-dichloro-3-(2-furoyl)-4-azaoxindole according to the procedure of Example 1C, using 5,6-dichloro-3-(2-furoyl)-4-azaoxindole (721 mg, 2.41 mmol), triethylamine (1.8 mL, 15.4 mmol), t-butyl isocyanate (1.4 mL, 12.3 mmol) and DMSO (20 mL). The reaction time was 22 hours. The crude product was triturated with methanol and recrystallized from hexane. Yield: 218 mg (23%). Analysis calc’d for C17H15Cl2N3O4: C 51.53, H 3.82, N 10.60. Found: C 51.70, H 3.81, N 10.57. M.p. 205 – 206C. 1H NMR (DMSO-d6) delta 9.37 (br s, 1H), 8.32 (s, 1H), 7.91 (s, 1H), 7.85 (d, J = 3.7 Hz, 1H), 6.69 (d, J = 3.7 Hz, 1H), 1.38 (s, 9H). IR (KBr disc) 1730, 1620, 1605, 1590, 1555, 1535 cmmin1. MS m/e (relative percent) 397(0.5), 395(2), 298(21), 296(33), 230(62), 228(100), 95(40).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,136888-26-1, 5,6-Dichloro-1H-pyrrolo[3,2-b]pyridin-2(3H)-one, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER INC.; EP436333; (1991); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 26218-75-7, 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.26218-75-7, name is Methyl 6-bromopicolinate, molecular formula is C7H6BrNO2, molecular weight is 216.03, as common compound, the synthetic route is as follows.

Into a 2000-mL 4-necked round- bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed methyl 6-bromopyridine-2-carboxylate (43.2 g, 199.97 mmol, 1.00 equiv), tetrahydrofuran (700 mL). This was followed by the addition of bromo(methyl)magnesium (150 mL) dropwise with stirring at 0C. The resulting solution was stirred overnight at room temperature. The mixture was then quenched by the addition of 200 mL of water. The resulting solution was extracted with 3×200 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×200 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 35 g (81%) of 2-(6-bromopyridin-2-yl)propan-2- ol as yellow oil.

The chemical industry reduces the impact on the environment during synthesis 26218-75-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (0 pag.)WO2019/165204; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 866545-96-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 866545-96-2, name is 1-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of l-(5-bromo-lH-pyrrolo[2,3-b]pyridin-3-yl)ethanone (50 g, 0.21 mol) in tetrahydrofuran (1400 mL) was added sodium hydride (8.8 g, 0.22 mol, 60 %) at 0 C. After the mixture was stirred for 1 h at 0 C a solution of 4-methylbenzene-l-sulfonyl chloride (48.3 g, 0.25 mol) in tetrahydrofuran (300 mL) was added dropwise at 0 C. The resulting mixture was warmed up to RT and stirred overnight. The reaction mixture was poured into ice water and extracted with ethyl acetate (3 xlOOO mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness in vacuo affording crude l-(5-bromo-l-tosyl-lH-pyrrolo[2,3-b]pyridin-3-yl)ethanone as yellow solid (75 g, yield: 90 %), which was used for the next step without further purification: NMR (400 MHz, DMSO-d6): delta 8.884 (s, 1H), 8.532-8.573 (m, 2H), 8.054-8.075 (d, J = 12 Hz, 2H), 7.442-7.463 (d, J = 8.4 Hz, 2H), 2.578 (s, 3H), 2.347 (s, 3H

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 866545-96-2, 1-(5-Bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ESTRADA, Anthony; LIU, Wen; PATEL, Snahel; SIU, Michael; WO2014/111496; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem