Potassium Hydroxide → 3-Acetylamino-6-chloro-2-[4-(hydroxymethyl)pyridine-2-carbonyl]indole

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Reaction Steps

To a solution of 3-acetylamino-6-chloro-2-[4-[(tert-butyldimethylsilyloxy)methyl]pyridine-2-carbonyl]indole (step 6, 240 mg, 0.454 mmol) in THF (10 ml) was added 1M TBAF in THF (0.7 ml, 0.681 mmol) at 0° C. After stirring for 30 min, potassium hydroxide (90 mg, 1.36 mmol) in water (2 ml) was added at 0° C. The mixture was stirred for an additional 1 h at room temperature and concentrated. The residue was diluted with ethyl acetate (100 ml), and then washed with water (30 ml×2) and dried (MgSO4). Removal of solvent gave a crystalline residue, which was recrystallized from dichloromethane to afford 52 mg (33%) of the title compound. m.p.: 216-218° C. (recrystallized from dichloromethane)

Provenance & Evidence