Dichloromethane → HCID 68846701, compound

Participants

Reaction Steps

Sodium hydroxide (0.154 g. 3.85 mmol) in 2 mL water was added to 3,5-dichloro-benzenethiol (0.328 g, 1.83 mmol) in 5 mL of ethanol. After 10 min stirring, 3-chloromethyl-pyridine hydrochloride (0.301 g, 1.83 mmol) in 2 mL water was added slowly. The resulting reaction mixture was stirred at room temperature overnight. Methylene chloride was added to the reaction mixture. The organic phase was washed with saturated aqueous sodium bicarbonate solution and brine. After removal of the solvent, the crude product was purified with flash chromatography to give 0.470 g (95% yield) of 3-(3,5-dichloro-phenylsulfanylmethyl)-pyridine. This compound was converted to N-[3-(1H-indol-4-yl)-5-(pyridin-3-ylmethylsulfanyl)-phenyl]-acetamide as described in Example 35. 1H NMR (400 MHz, CD3OD): δ 8.42 (s, 1H), 8.35 (d, J=4.7 Hz, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.66 (s, 2H), 7.38-7.31 (m, 2H), 7.27-7.23 (m, 2H), 7.13 (t, J=7.7 Hz, 1H), 6.97 (d, J=7.2 Hz, 1H), 6.44 (d, J=3.1 Hz, 1H), 4.20 (s, 2H), 2.12 (s, 3H).

Provenance & Evidence