Dimethylformamide → HCID 59278503, compound

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (PS-resin bound, 287 mg) and palladium acetate (70 mg, 0.31 mmol) were combined in a pressure vial. Dimethylformamide (3 mL) was added. The vial was flushed with nitrogen and a septa was affixed. The mixture was stirred at room temp. for 1 h, then the septa was removed and zinc cyanide (367 mg, 3.13 mmol) was added, followed by 2-methylpropane 2-sulfinic acid [(S)-1-(2-bromo-pyridin-4-yl)-propyl]-amide (1.00 g, 3.13 mmol) in dimethylformamide (7 mL). The vial was again flushed with nitrogen and sealed. The reaction was allowed to heat at 140° C. in an oil bath for 1 h. The solids are filtered of using a glass frit and rinsed with diethylether. The filtrate was diluted with diethylether and extracted with water (2×40 mL) and with brine (40 mL). The organic phase was dried with sodium sulfate and concentrated. The residue was purified by prepHPLC (eluted with 15-85% acetonitrile in water, with 0.1% TFA). Fractions were concentrated to remove acetonitrile, basified by sat. sodium bicarbonate solution, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated to yield 2-methyl-propane-2-sulfinic acid [(S)-1-(2-cyano-pyridin-4-yl)-propyl]-amide as a colorless oil (460 mg, 55%).

Provenance & Evidence