3-Hydroxypyridine → HCID 19348004, compound

Participants

Reaction Steps

3-Hydroxypyridine (57 mg, 0.6 mmol) was added to a stirred suspension of sodium hydride (24 mg of 60% dispersion in mineral oil, 0.6 mmol) in anhydrous dimethylformamide (2 ml), under a nitrogen atmosphere. After 30 minutes, ethyl 3-[(3-methoxyphenyl)sulfinyl]-6-[(methylsulfonyloxy)methyl]benzo[b]thiophene-2-carboxylate (Preparation 18, 234 mg, 0.5 mmol) was added to the mixture, and the mixture was stirred for 3 hours. The reaction was partitioned between ethyl acetate and water. The organics were separated and washed with water, dried (magnesium sulfate) and evaporated under reduced pressure. The residue was flash chromatographed on silica gel using 2% ethanol in dichloromethane as eluant The semi-pure product was re-chromatographed on silica gel using ethyl acetate, and then crystallised from diethyl ether, to give the title compound as a colourless solid (110 mg).

Provenance & Evidence