Sodium hydride → HCID 22241381, compound

Participants

Reaction Steps

The free base of 2-(chloromethyl)quinoline hydrochloride (148 mg, 0.69 mmol) is prepard by partioning the material between ethyl ether and sodium bicarbonate and drying the organic phase with magnesium sulfate. This material is then dissolved with isobutyl 2-[3-(hydroxy)-phenylsulfanylmethyl]-6-methyl-benzoate (220 mg, 0.67 mmol, example 83) in DMF (2 mL) at 0° C. and sodium hydride (60%, 27 mg 0.67 mmol) is added. The reaction is allowed to stir 16 h and is then partitioned between ethyl acetate and water. The organic phase is washed with water (3×), dried over magnesium sulfate, concentrated and purified by column chromatography (silica, 10% ethyl acetate in hexanes) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 8.19 (d, 1H), 8.08 (d, 1H), 7.83 (d, 1H), 7.74 (t, 1H), 7.63 (d, 1H), 7.55 (t, 1H), 7.18–7.07 (m, 4H), 6.99 (d, 1H), 6.89 (d, 1H), 6.82 (dd, 1H), 5.33 (s, 2H), 4.18 (s, 2H), 4.10 (d, 2H), 2.36 (s, 3H), 2.07–2.01 (m, 1H), 0.98 (d, 6H); MS (ESI) 472 (M+H)+.

Provenance & Evidence