Water → HCID 68859841, compound

Participants

Reaction Steps

Boron tribromide (41.4 mL of a 1 M solution in methylene chloride; 41.4 mmol) was added under nitrogen dropwise over 30 minutes to a solution of 1-benzyl-N-[(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methyl]-N-methyl-1H-indole-3-carboxamide (7.46 g, 13.8 mmol), prepared in the previous step, in 200 mL of methylene chloride at dry ice-acetone temperature. After the addition the dry ice-acetone bath was replaced with an ice bath and the stirring was continued for 3.5 h. At ice bath temperature 50 mL of water was added dropwise. The reaction was then partitioned between additional amounts of methylene chloride and water. The aqueous layer was separated and extracted three times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure to give 1-benzyl-N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-N-methyl-1H-indole-3-carboxamide (7.13 g, 98%) as a light tan solid, mp 164-170° C. Elemental Analysis for C30H25BrN2O2 Calc'd: C, 68.58; H, 4.80; N, 5.33. Found: C, 67.27; H, 4.78; N, 5.19

Provenance & Evidence