Water → 2-{[3-(Hydroxymethyl)phenyl]sulfanyl}pyridine-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Dissolve 3-(4-cyano-pyridin-2-ylsulfanyl)-benzoic acid (920 mg, 3.59 mmol) in thionyl chloride (50 mL) and stir. Heat to reflux. After 2 hours, concentrate under reduced pressure to give a residue. Dissolve residue in dioxane (100 mL) and add sodium borohydride (1.36 g, 35.9 mmol). Heat to 50° C. After 2 hours, cool to ambient temperature and add water. Extract with ethyl acetate, combine organic layers, dry with sodium sulfate, filter and concentrate to give the title compound as a yellow oil (378 mg, 44%): 1H NMR (DMSO-d6) δ 4.56 (d, 2H), 5.31 (t, 1H), 7.38 (m, 1H), 7.48 (m, 3H), 7.55 (m, 1H), 7.59 (dd, 1H), 8.62 (dd, 1H).

Provenance & Evidence