Isopropanol → Ammonia

Participants

Reaction Steps

A solution of 5-fluoro-N-(trans-4-hydroxy-cyclohexyl)-2-(3-methylsulfanyl-phenoxy)-nicotinamide (70 mg, 0.18 mmol) in tetrahydrofuran (1 ml) was added to a solution of oxone™ (229 mg, 0.37 mmol) in water (1 ml) and isopropylalcohol (4 ml) under nitrogen at room temperature and the reaction was stirred for 3 h. The reaction mixture was passed through a chemelute cartridge, washing with tetrahydrofuran, and the eluent was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:concentrated aqueous ammonia (98:2:0.2 changing to 96:4:0.4, by volume) to give 5-fluoro-N-(trans-4-hydroxy-cyclohexyl)-2-(3-methylsulfonyl-phenoxy)-nicotinamide (50 mg) as a yellow solid.

Provenance & Evidence