Category: 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.SDS of cas: 1211530-54-9

Racemic 8-bromo-2,2-difluoro-2H-1 ,4-benzoxazin-3(4H)-one (50 mg, 0.189 mmol, intermediate 4), 5-(bromomethyl)-3-pyridinecarbonitrile (37.3 mg, 0.189 mmol, intermediate 24), potassium carbonate (52.3 mg, 0.379 mmol) and potassium iodide (0.314 mg, 1.894 mumol) were dissolved in DMF (3000 mul) in a 10 ml. round-bottomed flask open to the atmosphere and stirred at room temperature overnight. The reaction mixture was evaporated to dryness, redissolved in EtOAc (30ml) and treated with saturated aqueous sodium bicarbonate (30ml). The aqueous layer was extracted with EtOAc (2x30ml) and the organic layers were combined, washed with brine (30ml), dried over magnesium sulfate, filtered and evaporated to dryness to give the crude product (119mg) as a light brown oil. The crude product was purified on a 25+S Biotage silica cartridge, eluting with a 0 to 70% mixture of EtOAc in hexane. This gave an off-white solid (54 mg). 47 mg of this racemic mixture was resolved using a Chiralpak AS column eluting with heptane: ethanol (90:10) v/v pump-mixed. Using these conditions the faster- running enantiomer (20 mg, Compound 57 or 58) and the slower-running enantiomer (15 mg, Compound 57 or 58) were obtained in >99% enantiomeric excess. 1H NMR (CD3OD) delta: 1.45 (3H, d), 5.23 (1 H, q), 5.41 (2H, s), 7.18 (1 H, dd), 7.25 (1 H, t), 7.42 (1 H, dd), 8.14 (1 H, s), 8.78 (1 H, d), 8.84 (1 H, d). m/z [M+H]+: 345.9. Retention time 0.81 min (LC/MS method 3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,1211530-54-9, 5-(Bromomethyl)nicotinonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; BLUNT, Richard; EATHERTON, Andrew John; GARZYA, Vincenzo; HEALY, Mark Patrick; MYATT, James; PORTER, Roderick Alan; WO2011/12622; (2011); 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