Water → 3-Acetylamino-7-chloro-2-[(N-methoxy-N-methylamino)carbonyl]indole

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Reaction Steps

To a solution of 3-amino-7-chloro-2-[(N-methoxy-N-methylamino)carbonyl]indole (step 3, 287 mg, 1.1 mmol) in dichloromethane (10 ml) was added pyridine (2 ml) and acetic anhydride (0.16 ml, 1.7 mmol) at room temperature. After stirring for 3 h, the mixture was poured into water (100 ml) and extracted with ethyl acetate (150 ml). The organic layer was washed with 2N aquous HCl (100 ml), water (100 ml), saturated aqueous sodium bicarbonate (100 ml), brine (100 ml), and dried (MgSO4). After removal of solvent, the residue was purified by flash column chromatography eluting with ethyl acetate/hexane (1:101:1) to give 320 mg (98%) of the title compound.

Provenance & Evidence