Benzyl mercaptan → HCID 71186444, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2,3-dimethoxypyridine (1.2 g, 5.50 mmol) in toluene (18 ml) was added phenylmethanethiol (0.71 ml, 6.05 mmol), N-ethyl-N-isopropylpropan-2-amine (2.00 ml, 12.1 mmol), Pd2(dba)3 (0.20 g, 0.22 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (0.26 g, 0.44 mmol) at room temperature under an atmosphere of nitrogen. The reaction mixture was irradiated in the microwave with heating to 120° C. for 1 hour before being filtered through a pad of celite and washed with ethyl acetate (25 ml). The filtrate was concentrated to give an orange oil which was purified by column chromatography (SiO2; 0-15% ethyl acetate in petrol) gave 5-(benzylsulfanyl)-2,3-dimethoxypyridine as an orange oil (1.52 g, 75%).

Provenance & Evidence