Methanol → HCID 10150405, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (4-methoxy-7-phenyl-benzo[b]thiophen-2-yl)-amine (100 mg, 0.392 mmol) in THF (8 ml) and diethylisopropyl amine (0.147 ml, 2.2 eq.) was stirred together at −10° C. under an argon atmosphere. To this was slowly added 6-methyl-nicotinyl chloride hydrochloride (83 mg, 0.431 mmol, 1.1 eq) in dichloromethane (5 ml) and the mixture stirred to 20° C. overnight. The reaction was again cooled to 0° C. and Methanol was then added (1.2 ml) and the mixture stirred for 30 min to 20° C. The mixture was then evaporated to dryness and chromatographed over silica gel eluting with a gradient of heptane/EtOAc (1:1 to 1:8). The product fractions were pooled and evaporated to afford the title compound (83 mg, 57% yield) as a yellow solid MS: m/e=375.4 (M+H+).

Provenance & Evidence