Thiophenol → 6-(Benzylsulfanyl)-2,3-dimethoxypyridine

Participants

Reaction Steps

To a solution of 6-iodo-2,3-dimethoxypyridine (0.3 g, 1.13 mmol) in toluene (10 ml) was added phenyl mercaptan (0.21 g, 1.7 mmol) and DIPEA (0.32 g, 2.5 mmol). The reaction mass was degassed before Pd2(dba)3 (0.04 g, 0.05 mmol) and Xantphos (0.05 g, 0.1 mmol) were added and the whole was subjected to microwave irradiation at 120° C. with stirring for 2 hours. The resulting mixture was filtered through a pad of celite and the filtrate was added to water (60 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were dried (Na2SO4) and then concentrated. The crude product was purified by column chromatography (SiO2; 0-5% ethyl acetate/petrol) and product fractions concentrated to yield 6-(benzylsulfanyl)-2,3-dimethoxypyridine (0.2 g, 68%).

Provenance & Evidence