(Dimethyl sulfide)trihydroboron → HCID 13649440, compound

Participants

Reaction Steps

To a refluxing solution of 1.6 g of 2-(p-bromophenyl)-6-cyano pyridine in 8 ml of tetrahydrofuran is added slowly a solution of 0.92 ml of borane-dimethylsulfide in 6 ml. of tetrahydrofuran. Dimethyl sulfide is simultaneously removed by distillation through a 10 cm vigreux column. The mixture is refluxed for 15 minutes after the addition is complete, cooled to 30°, and 6 ml of 6N hydrochloric acid is added. After hydrogen evolution has ceased, the reaction is refluxed for 30 minutes, cooled to 0°, saturated with solid sodium carbonate and extracted with 4×50 ml aliquots of methylene chloride. The methylene chloride solution is evaporated and the residue is chromatographed through 10.0 g of silica gel with 1:1 methanol-ethyl acetate as eluent to yield 2-aminomethyl-6-(p-bromophenyl)pyridine melting at 71°-75°.

Provenance & Evidence