(5-Bromo-3-pyridinyl)methanol → HCID 68537937, compound

Participants

Reaction Steps

Dissolve 3-bromo-5-hydroxymethyl-pyridinium chloridei [Kelly, T. R., Howard, H. R., Koe, K., Sarges, R. J. Med. Chem. 1985, 28, 1368-1371] (1.00 g, 4.45 mmol) in saturated aqueous sodium bicarbonate, extract three times with ethyl acetate, dry combined organic phases over sodium sulfate, condense to afford (5-bromo-pyridin-3-yl)-methanol. Employing the procedure of general method 1 using (5-bromo-pyridin-3-yl)-methanol (832 mg) and 3-mercapto-benzoic acid methyl ester (1.50 g, 8.91 mmol). Purify by SCX column, elute with dichloromethane, then 1:1 dichloromethane/methanol then 1:1 dichloromethane/methanol, 10% ammonia, compound elutes in the ammonia, to yield the title compound as a dark brown oil (380 mg, 1.38 mmol): MS (m/z): 276 (M+1).

Provenance & Evidence