2-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one → 1-(3,4-dihydroquinolin-1(2H)-yl)-2-(3-methylbenzo[b]thiophen-2-ylthio)-ethanone

Participants

Reaction Steps

Compound 75 was obtained according to the procedure used to synthesize compound 72, except the addition of sulfur was done at 40° C. in an attempt to avoid significant formation of disulfide. The obtained crude material (75) was used for the next step without further purification. 1-(3,4-dihydroquinolin-1(2H)-yl)-2-(3-methylbenzo[b]thiophen-2-ylthio)-ethanone (76): Crude compound 75 (0.55 g, 3.0 mmol) was coupled with compound 4 (0.48 g, 2.3 mmol) according to procedure used to synthesize compound 73. The product was purified by column chromatography to yield compound 76 (95 mg, 5% for two steps): MS: m/z+354.1 [M+H]+; Anal. Calcd (found) for C20H19NOS2.0.1H2O: C, 67.61; (67.59), H, 5.45; (5.48), N, 3.94; (3.94), S, 18.05; (17.75).

Provenance & Evidence