Hydrochloric Acid → HCID 12968631, compound

Participants

Reaction Conditions

Reaction Steps

Under an atmosphere of argon, 2-amino-4-(1,3-benzodioxol-5-yl)-6-(phenyl-sulfanyl)-3,5-dicyanopyridine [preparation analogously to J. M. Quintela, J. L. Soto, Anales de Quimica 79, 368–372 (1983)] (100 mg, 0.27 mmol) is dissolved in absolute THF (3 ml). 1,3-Bis(diphenylphosphino)propanedichloronickel(II) (4.4 mg, 0.008 mmol) is added, the color of the solution changing to pink. On slow dropwise addition of cyclopropylmagnesium bromide (1M solution in THF; 0.644 ml, 0.644 mmol), a clear change in color to brown-red can be observed. The solution is heated at 50° C. for 3 hours. After only about 5 minutes, the solution turns green. 1N hydrochloric acid (1 ml) is added and the mixture is then diluted with diethyl ether. Solid sodium carbonate and water are added. The phases are separated and the organic phase is dried over magnesium sulfate, filtered and concentrated. The mixture is separated by silica gel column chromatography (toluene:ethyl acetate=2:1).

Provenance & Evidence