Boron tribromide → HCID 10662673, compound

Participants

Reaction Steps

To a solution of 165 mg (0.51 mmol) of 5-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide (Example 17, Part B) in 30 mL of CH2Cl2 was added 1.0 mL of 1M BBr3 in CH2Cl2 and the mixture stirred for 1.5 hours, then an addition 0.5 mL of the BBr3 solution was added. After 1.5 hours, the reaction mixture was washed with Na2CO3 solution, dried (Na2SO4), and concentrated at reduce pressure. The residue was chromatographed on silica eluting with 2% MeOH/CH2Cl2 →5% MeOH/CH2Cl2 to give 60 mg (39% yield) of 5-hydroxy-2-methyl-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide, mp, 216°-219° C.

Provenance & Evidence