3-Pyridinemethanol → HCID 21186293, compound

Participants

Reaction Steps

Oil-free sodium hydride (240 mg) was added to a stirred solution of 3-pyridyl carbinol (1.09 g) in dry THF (20 ml). When evolution of hydrogen ceased, 2-(4-bromomethylphenyl)-N-(isobutoxycarbonyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (549 mg) was added and the mixture was stirred for 2 hours. Volatile material was removed by evaporation and saturated ammonium chloride solution (10 ml) was added to the residue. The mixture was extracted with ethyl acetate (3×20 ml) and the extracts were dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by flash chromatography, eluting with methanol/ethyl acetate (1:19 v/v), to give after trituration with ether N-(3-methoxy-5-methylpyrazin-2-yl)-2-{4-[(3-pyridyl)methoxymethyl]phenyl}pyridine-3-sulphonamide (187 mg), m.p. 183-185° C.; microanalysis found: C, 60.9; H, 4.9; N, 14.2%; C24H23N5O4S requires: C, 60.4; H, 4.85; N, 14.7%.

Provenance & Evidence