Methanol → HCID 19042867, compound

Participants

Reaction Steps

5-(Pyrid-2-ylthio)indole (0.347 g, 1.53 mmol), 1-methylpiperid-4-one (0.347 g, 0.38 mL, 3.06 mmol), sodium methoxide (0.497 g) and some finely ground molecular sieves were heated in refluxing MeOH (20 mL) for 24 hr. After work-up and chromatography (silica gel; CH2Cl2 /MeOH; 0-15%), 3-(1-methyl-1,2,5,6-tetrahydropyrid-4-yl)-5-(pyrid-2-ylthio)indole was obtained as a yellow solid (0.35 g). This was treated with fumaric acid (0.189 g, 1.6 mmol) in MeOH/Et2O to give, as a pale yellow crystalline solid: 3-(1-methyl-1,2,5,6-tetrahydropyrid-4-yl)-5-(pyrid-2-ylthio)indole fumarate, 0.227 g (34%), m.p. 226°-28° C.

Provenance & Evidence