Water → 3-Acetylamino-6-chloro-2-(3-methoxybenzoyl)indole

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Reaction Steps

To a solution of 3-amino-6-chloro-2-(3-methoxybenzoyl)indole (Example 18, 413 mg, 1.37 mmol) in dichloromethane (20 ml) was added pyridine (0.33 ml, 4.12 mmol) and acetyl chloride (0.14 ml, 2.06 mmol). After stirring for 0.5 h, water (1 ml) and diethyl ether (100 ml) were added, and the mixture washed consecutively with 1N aqueous HCl (50 ml×2) and saturated aqueous sodium bicarbonate (50 ml×2). The organic layer was dried (MgSO4) and solvent removed. The resultant residue was purified by flash chromatography eluting with ethyl acetate/hexane (1:2) to afford the title compound as an oil. Crystallization from ethanol/hexane to give 260 mg (55%) of title compound. m.p.: 161-162° C. 1H-NMR (CDCl3) δ: 9.92 (1H, br s), 8.32 (1H, br s), 8.22 (1H, d, J=9.2 Hz), 7.47 (1H, dd, J=7.7 and 8.1 Hz), 7.37-7.26 (3H, m), 7.18-7.08 (1H, m), 7.10 (1H, dd, J=1.6 and 9.0 Hz), 3.88 (3H, s), 2.25 (3H, s)

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