6-BROMO-5-METHYLINDOLE

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 6-bromo-5-methylindole (1.00 g, 4.75 mmol) in AcOH (150 mL) was treated with NaBH3CN (0.897 g, 14.3 mmol) while maintaining a temperature of −10° C. The mixture was then stirred at RT overnight and concentrated. The resulting residue was treated with aqueous K2CO3, and extracted with DCM (3×100 mL). The combined organic layers were dried over MgSO4, concentrated and purified by column chromatography (0-75% EtOAc/hexanes) to afford 6-bromo-5-methylindoline (13A, 716 mg). concentrated The resulting residue was treated with aqueous K2CO3 extracted with DCM (3×100 mL) The combined organic layers were dried over MgSO4 concentrated purified by column chromatography (0-75% EtOAc/hexanes)