tert-butyl 4-(5-bromo-7-carbamoyl-1H-indol-3-yl)piperidine-1-carboxylate → 5-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide

Participants

Reaction Steps

To a solution of 1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-bromo-1H-indol-3-yl]-1-piperidinecarboxylate (1.56 g, 3.7 mmol) in methanol (10 mL), HCl in dioxane (4M, 35.5 mL) was added. The reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure and the resulting residue was partitioned between ethyl acetate (50 mL) and 5% of aqueous NaOH (50 mL). The aqueous layer was washed with ethyl acetate (2×50 mL) and the combined organic phases were dried with MgSO4 and concentrated under reduced pressure to give the desired product (685 mg, 58%), which was used in the next step without further purification.

Provenance & Evidence