1-Hexanethiol → N-(6-Methylthioquinolin-5-yl)-2-(hexylthio)-decanoic amide

Participants

Reaction Steps

(S)-N-(6-Methylthioquinolin-5-yl)-2-bromodecanoic amide (39 mg, 0.09 mmol) in 1 ml of dry THF was added slowly to a suspension containing cesium carbonate (67 mg, 0.20 mmol) and hexanethiol (13 mg, 0.11 mmol) in 2 ml of THF. After 18 hours, the reaction was quenched with 2 ml of 1N HCl and extracted with ethyl acetate (4×10 ml). The organic phase was purified by silica gel column chromatography (eluent: 100% CHCl3) to yield 25 mg (60% yield) of the desired product. 1H NMR (CDCl3) δ8.85 (1H, d, J=3 Hz), 8.62 (1H, s), 8.05 (1H, d, J=9 Hz), 8.00 (1H, d, J=9 Hz), 7.65 (1H, d, J=9 Hz), 7.40 (1H, dd, J=9, 9 Hz), 3.55 (1 H, t, J=8 Hz), 2.80 (2H, t, J=8 Hz), 2.50 (3H, s), 2.20-1.30 (22H, m), 0.91 (6H, t, J=Hz).

Provenance & Evidence