Sodium Hydroxide → 1-cyclobutyl-6-hydroxy-1H-indole-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

1-cyclobutyl-6-methoxy-1H-indole-3-carbonitrile (100 g, 442 mmol) was dissolved in CH2Cl2 (700 mL) and cooled to −20° C. Boron tribromide (300 g, 1.2 mol) was added dropwise over 2.5 hours to the cooled solution. The reaction was poured into ice water (2 L), neutralized to pH 7 with 5 N aq. sodium hydroxide and stirred overnight at room temperature. The remaining organic solvent was evaporated and the resulting suspension was filtered. The solid was washed with water (2×200 mL), 1/1 hexane/ethyl ether (2×125 mL) and dried in a stream of nitrogen to give 1-cyclobutyl-6-hydroxy-1H-indole-3-carbonitrile as a beige powder (90.0 g, 96%).

Provenance & Evidence