Sodium Bicarbonate → HCID 58636802, compound

Participants

Reaction Steps

To a solution of [5-(3-cyano-benzyloxy)-4-(1-hydroxy-ethyl)-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (112) (245 mg, 0.10 mol) in dry dichloromethane (7 mL) was slowly added bis(2-methoxyethyl)aminosulfur trifluoride (350 mg, 1.6 mol) at 0° C. under nitrogen atmosphere. The reaction was slowly warmed to room temperature and stirred for 30 minutes. The reaction mixture was then poured into a cold solution of saturated aqueous sodium bicarbonate, and the crude product extracted with dichloromethane, dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude residue, which was purified by column chromatography on silica gel using a gradient mixture of ethyl acetate:hexane (0:1 to 1:1) as an eluant to give [5-(3-cyano-benzyloxy)-4-(1-fluoro-ethyl)-6-methyl-pyridin-3-ylmethyl]-(4-cyano-phenyl)-carbamic acid tert-butyl ester (113) (54 mg, 22% yield) and 4-[3,5-dimethyl-4-(3-cyano-benzyloxy)-7-oxo-5,9-dihydro-6-oxa-2,8-diaza-benzocyclohepten-8-yl]-benzonitrile (114) (90 mg, 43% yield).

Provenance & Evidence