Benzyl Bromide → 1-[5-Chloro-1-(phenylmethyl)-1h-indol-2-yl]pentan-1-one

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Reaction Steps

To a solution of the title compound of Example 3 Step A (1.35 g, 5.73 mmol) in DMF (25 mL) was added NaH (252 mg, 60% suspension if mineral oil, 6.30 mmol). After 20 min, benzyl bromide (0.750 mL, 6.30 mmol) was added, and the mixture was allowed to stir for 15 h, whereupon it was quenched by addition of sat. aq. NH4Cl. The aqueous phase was extracted with EtOAc, and the organic phase was dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 15%, then 15 to 100% EtOAc in hexanes) provided the title compound: LCMS A, tr=4.36 min, m/z 326.2 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 7.74 (d, J=1.0 Hz, 1H), 7.34-7.22 (m, 6 H), 7.04 (d, J=7.0 Hz, 2H), 5.88 (s, 2H), 2.99 (t, J=7.5 Hz, 2H), 1.76-1.70 (m, 2H), 1.44-1.36 (m, 2 H), 0.97 (t, J=7.0 Hz, 3H).

Provenance & Evidence