(Diethylamino)sulfur trifluoride → HCID 68644476, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{[5-(4-cyano-benzyloxy)-4-hydroxymethyl-6-methyl-pyridin-3-ylmethyl]-amino}-benzonitrile (8) (1765 mg, 4.60 mmol) in dry dichloromethane (200 mL) was slowly added diethylaminosulfurtrifluoride (DAST) (741 mg, 4.6 mmol) in dry dichloromethane (50 mL) at −78° C. under nitrogen atmosphere. The reaction temperature was warmed to −40° C. and stirred for 30 minutes. The reaction mixture was then poured into a cold solution of saturated aqueous sodium bicarbonate, and the crude product was extracted with dichloromethane, washed with water, and dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude residue, which was purified by column chromatography on silica gel using dichloromethane:hexane:methyl alcohol (15:10:1) as an eluant to give 4-{[5-(4-cyano-benzyloxy)-4-fluoromethyl-6-methyl-pyridin-3-ylmethyl]-amino}-benzonitrile (10) (650 mg, 37% yield) as a colorless solid.

Provenance & Evidence