Tag: M.W:200-300

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.851607-27-7, name is 5-Bromo-4-chloro-2-methoxypyridine, molecular formula is C6H5BrClNO, molecular weight is 222.47, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-4-chloro-2-methoxypyridine

To a solution of cyclopropylmethanol (446 mg, 6.18 mmol) in THF (10 mL) was added NaH (247 mg, 6.18 mmol, 60% in mineral oil) in one portion at 0 C. The reaction mixture was warmed up to 20 C. over a period of 30 mins and stirred at 20 C. for 10 mins. Then 5-bromo-4-chloro-2-methoxypyridine (550 mg, 2.47 mmol) was added in one portion and the mixture was stirred at 70 C. for 4 hours. The mixture was diluted with saturated ammonium aqueous solution (50 mL) and extracted by EtOAc (2*30 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated to give the crude product which was purified by silica gel column chromatography (PE:EA=20:1 to 10:1) to afford the title compound (450 mg, 70.6%) as colorless oil. 1H NMR: (CDCl3, 400 MHz) delta: 8.11 (s, 1H), 6.18 (s, 1H), 3.90 (s, 3H), 3.89-3.88 (m, 2H), 1.39-1.27 (m, 1H), 0.70-0.67 (m, 2H), 0.46-0.43 (m, 2H). LCMS (M+H)+=258.0 (M+1)+; 260.0

At the same time, in my other blogs, there are other synthetic methods of this type of compound,851607-27-7, 5-Bromo-4-chloro-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Bennett, Michael John; Betancort, Juan Manuel; Boloor, Amogh; Kaldor, Stephen W.; Stafford, Jeffrey Alan; Veal, James Marvin; US2015/111885; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1231930-13-4 , The common heterocyclic compound, 1231930-13-4, name is 3-Bromo-2-methyl-6-nitropyridine, molecular formula is C6H5BrN2O2, 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.

A mixture of Example C7 (1.185 g, 3.93 mmol), Example A6 (0.746 g, 2.81 mmol), K2CO3 (1.165 g, 8.43 mmol) and Pd(PPh3)4 (0.325 g, 0.281 mmol) in dioxane (11 mL) and water (3 mL) was sparged with Ar and heated at 90 C. overnight. The mixture was cooled to RT, treated with EtOAc and brine and the solids removed via filtration through diatomaceous earth. The layers of the filtrate were separated, the aqueous layer extracted with additional EtOAc (3*) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 2-methyl-3-((2-(4-(1-methylpiperidin-4-yl)phenyl)pyridin-4-yl)oxy)-6-nitropyridine (553 mg, 49%). MS (ESI) m/z: 405.2 (M+H+).

The synthetic route of 1231930-13-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Deciphera Pharmaceuticals, LLC; Flynn, Daniel L.; Kaufman, Michael D.; Samarakoon, Thiwanka; Caldwell, Timothy Malcolm; Vogeti, Lakshminarayana; Ahn, YuMi; Patt, William C.; Yates, Karen M.; US2014/315917; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 161117-83-5, tert-Butyl (2-methoxypyridin-3-yl)carbamate, 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, Recommanded Product: tert-Butyl (2-methoxypyridin-3-yl)carbamate, blongs to pyridine-derivatives compound. Recommanded Product: tert-Butyl (2-methoxypyridin-3-yl)carbamate

49. Preparation of t-Butyl N-(4-Fluoro-2-methoxy-3-pyridinyl)carbamate To a solution of 8 g (35.7 mmol) of t-butyl N-(2-methoxy-3-pyridyl)carbamate in 200 mL of dry tetrahydrofuran was added with stirring at -60 C., 46.2 mL (78.5 mmol) of 1.7M t-butyl lithium in pentane. The resulting solution was allowed to warm slowly with stirring to -20 C. over a 20 to 30 min period. It was then cooled to about -60 C. and 12.2 g (38.7 mmol) of N-fluorodibenzenesulfonimide was added with stirring all at once. The mixture was allowed to warm to -20 C. and was poured into 500 mL of ether. The resulting ethereal solution was washed with a mixture of 2.5 g (41.7 mmol) of acetic acid and 150 mL of water. The aqueous phase was extracted with 200 mL of ether. The ethereal extracts were combined, dried over magnesium sulfate, filtered, and concentrated by evaporation. The residue was purified by flash chromatography to obtain 6.7 g (77 percent of theory) of the title compound as a colorless solid melting at 75-77 C. Elemental Analysis C11 H15 FN2 O3 Calc.: %C, 54.5; %H, 6.24; %N, 11.6 Found: %C, 54.2; %H, 6.39; %N, 11.4 1 H NMR (CDCl3): 7.88 (dd, 1H, j=5.8, 7.6); 6.68 (dd, 1H, j=5.8, 8.9); 5.9 (br, 1H); 3.9 (s, 3H); 1.45 (s, 9H).

The synthetic route of 161117-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DowElanco; US5571775; (1996); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 1111637-74-1, 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.1111637-74-1, name is 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone, molecular formula is C7H5BrFNO, molecular weight is 218.02, as common compound, the synthetic route is as follows.

Step 4. (R,E)-N-(1-(5-bromo-2-fluoropyridin-3-yl)ethylidene)-2-methylpropane-2-sulfinamide To a solution of 1-(5-bromo-2-fluoropyridin-3-yl)ethanone (10.93 g, 50.1 mmol) in THF (100 ml) was added (R)-(+)-2-methyl-2-propanesulfinamide (12.15 g, 100 mmol) and titanium (IV)-ethoxide (20.75 mL, 100 mmol). The resulting mixture was then heated at reflux for 1 h. The mixture was cooled to RT and brine (300 mL) was added. The mixture was stirred at RT for 15 min, then filtered and the solid was washed with DCM (2*100 mL). The organic layer was collected and the aqueous layer was dried over MgSO4 and concentrated. The residue was then dissolved in DCM (10 mL) and purified by silica gel chromatography, eluent 0%-100% EtOAc/hexane, to give 14.9 g of the title compound as a yellow solid. MS (ESI, positive ion) m/z: 321, 323 (M+H).

Statistics shows that 1111637-74-1 is playing an increasingly important role. we look forward to future research findings about 1-(5-Bromo-2-fluoropyridin-3-yl)ethanone.

Reference:
Patent; LEWIS, Richard T.; ALLEN, Jennifer R.; CHENG, Yuan; CHOQUETTE, Deborah; EPSTEIN, Oleg; GUZMAN-PEREZ, Angel; HARRINGTON, Paul E.; HUA, Zihao; HUNGATE, Randall W.; HUMAN, Jason Brooks; JUDD, Ted; LIU, Qingyian; LOPEZ, Patricia; MINATTI, Ana Elena; OLIVIERI, Philip; ROMERO, Karina; RUMFELT, Shannon; RZASA, Robert M.; SCHENKEL, Laurie; STELLWAGEN, John; WHITE, Ryan; XUE, Qiufen; ZHENG, Xiao; ZHONG, Wenge; US2014/107109; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 60010-03-9, 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. 60010-03-9, name is 2,6-Dichloro-4-methyl-3-nitropyridine. A new synthetic method of this compound is introduced below.

To a solution of 2,6-dichloro-4-methyl-3-nitropyridine (6.5g; 31 .4 mmol) and TEA (10g; 3eq) in acetonitrile (200ml) was added (R)-(-)-3-fluoropyrrolidine hydrochloride (4.75g; 1 .2eq). The mixture was stirred for 4h at rt, after which the reaction mixture was quenched with sat NaHCOs(aq) (300ml), diluted with water and and EtOAc. The layers were separeted and the waterlayer was extracted with EtOAc (3x150ml_) untill no UV(254nm) active material was extracted). The combined organic layers were washed with brine and dried over Na2SO4(s). Filtration and in vacuo concentration resulted in a quantitative yield 8.36g of the title compound as a yellow/orange oil.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,60010-03-9, 2,6-Dichloro-4-methyl-3-nitropyridine, and friends who are interested can also refer to it.

Reference:
Patent; NEUROSEARCH A/S; BROWN, William, Dalby; JESSEN, Carsten; STRØBAeK, Dorte; WO2011/26890; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of 192447-58-8, 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.192447-58-8, name is 2,6-Dibromo-N,N-dimethylpyridin-4-amine, molecular formula is C7H8Br2N2, molecular weight is 279.9598, as common compound, the synthetic route is as follows.

Stage 1: Synthesis of 2,6-dibromo-4-(dimethylamino)pyridine-3,5-dicarbaldehyde 1 mole of 2,6-dibromo-4-(dimethylamino)pyridine may be treated with 2 moles of hexamethylenetetramine in trifluoroacetic acid at reflux for three hours. The solvent may be removed with a thin-film evaporator at elevated temperature and under reduced pressure. The residue may be dissolved in 1M hydrochloric acid, extracted with dichloromethane, and the organic phase may be isolated. The organic phase may be washed with brine and the solvent may be removed with a thin-film evaporator at elevated temperature and under reduced pressure to afford 2,6-dibromo-4-(dimethylamino)pyridine-3,5-dicarbaldehyde.

The chemical industry reduces the impact on the environment during synthesis 192447-58-8, I believe this compound will play a more active role in future production and life.

Reference:
Patent; Martineau, Louis C.; US2014/135359; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 73112-16-0, name is 2,6-Dibromo-4-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Computed Properties of C6H5Br2N

Compound II-2 (2.51 g, 10 mmol), Compound III (1.07 g, 10 mmol),Pd(OAc) 2 (0.22 g, 1 mmol), BINAP (2,2′-bisdiphenylphosphino-1,1′-binaphthyl,0.62 g, 1 mmol) and t-BuOK (2.24 g, 20 mmol) were added to 50 mL of dry 1,2-dimethoxyethane (DME).The reaction mixture was stirred overnight under a nitrogen atmosphere and was confirmed by TLC.The reaction mixture was carefully poured into 200 mL of ice water, stirred, and extracted with 50 mL×3 CH 2 Cl 2 .The extract phases were combined, washed with 1% diluted hydrochloric acid and brine and dried over anhydrous sodium sulfate.The desiccant was removed by suction filtration, and the filtrate was evaporated to dryness on a rotary evaporator.Compound IV-2 was obtained.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 73112-16-0, 2,6-Dibromo-4-methylpyridine.

Reference:
Patent; Foshan Hanfang Zhongyi Hospital Co., Ltd.; Zhu Bin; (8 pag.)CN109988147; (2019); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 1111637-94-5, Adding some certain compound to certain chemical reactions, such as: 1111637-94-5, name is 5-Bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine,molecular formula is C8H7BrN2, 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 1111637-94-5.

Preparation of 3-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrrolo[2,3-b]pyridine (B-5-5)To a solution of 5-bromo-3-methyl-1 H-pyrrolo[2,3-b]pyridine (B-5-4) (0.5 g, 2.37 mmol) in DMF (150 mL) were added KOAc (0.7 g, 7.11 mmol) and bis(pinacolato)diboron (0.72 g, 2.84 mmol). The resulting mixture was degassed under N2 for 2 minutes. Then Pd(PPh3J2CI2 (0.2 g, 0.237 mmol) was added and the mixture was degassed again. The reaction was heated to 80-900C and stirred overnight. The mixture was poured into water (30 mL), extracted with EtOAc (15 mLchi3). The organic layer was washed with saturated aqueous NaCI, dried over Na2SO4 and concentrated to give crude 3-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrrolo[2,3-b]pyridine (B-5-5) (0.7 g), which was used directly in next step.

According to the analysis of related databases, 1111637-94-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; WO2009/16460; (2009); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 116355-18-1, Adding some certain compound to certain chemical reactions, such as: 116355-18-1, name is 6-Bromo-7-methylimidazo[1,2-a]pyridine,molecular formula is C8H7BrN2, 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 116355-18-1.

To a solution of 6-bromo-7-methylimidazo(1,2-a)pyridine (9 g, 43.0 mmol) and anhydrous sodium acetate (9.52 g, 116.1 mmol) in MeOH (100 mL) at 0 C. was added iodine (12.0 g, 47.3 mmol). The reaction mixture was stirred at rt for 20 h. The precipitate was collected by filtration and washed with MeOH to afford 6-bromo-3-iodo-7-methylimidazo[1,2-a]pyridine (6 g, 41%) as a light grey solid. 1H NMR (400 MHz, CDCl3) delta 8.30 (s, 1H), 7.64 (s, 1H) 7.49 (s, 1H) 2.50 (s, 3H); MS (ESI) m/z 336.7 [M+H]+.

According to the analysis of related databases, 116355-18-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Agency for Science, Technology and Research; Nacro, Kassoum; Duraiswamy, Athisayamani Jeyaraj; Rao, Lohitha; US2014/371199; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Related Products of 62150-47-4, 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.62150-47-4, name is Ethyl 4-bromopicolinate, molecular formula is C8H8BrNO2, molecular weight is 230.06, as common compound, the synthetic route is as follows.

The second step: 8.5 kg of A was added to 35 liters of ammonia water in batches, methane was stirred overnight, and centrifuged to obtain a crude product which was washed with ethyl acetate and centrifuged to obtain 4.5 kg of amide;

Statistics shows that 62150-47-4 is playing an increasingly important role. we look forward to future research findings about Ethyl 4-bromopicolinate.

Reference:
Patent; Chengdu Tong Chuangyuan Pharmaceutical Technology Co., Ltd.; Shou Yuehan; (12 pag.)CN105153023; (2018); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem