Benzyl mercaptan → 6-(Benzylthio)-3-chloroisoquinoline

Participants

Reaction Conditions

Reaction Steps

A pressure vessel was charged with 6-bromo-3-chloroisoquinoline (1.3307 g, 5.49 mmol), Xantphos (0.159 g, 0.274 mmol), and Pd2(dba)3 (0.126 g, 0.137 mmol). The vessel was flushed with Ar (g), then 1,4-dioxane (10.97 ml), N,N-diisopropylethylamine (1.917 ml, 10.97 mmol), and benzyl mercaptan (0.682 ml, 5.76 mmol) were added in sequence. The vessel was sealed and heated in an 80° C. heating bath for 16 h. The mixture was cooled, diluted with EtOAc, and filtered through diatomaceous earth. The filtrate was concentrated, and the residue was purified by chromatography on silica gel (25-g silica gel loading column, 0 to 30% EtOAC/Heptane) to give 6-(benzylthio)-3-chloroisoquinoline (1.398 g, 4.89 mmol, 89% yield) as a light-yellow solid: 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=8.94 (s, 1H), 7.81 (d, J=8.6 Hz, 1H), 7.55 (d, J=0.2 Hz, 1H), 7.50-7.39 (m, 4H), 7.38-7.28 (m, 3H), 4.30 (s, 2H); m/z (ESI) 286.2 (M+H)+.

Provenance & Evidence