Hydrochloric Acid → N-benzyl-N-[(3'-bromo-4'-methoxy-1,1'-biphenyl-4-yl)methyl]-1-methyl-1H-indole-3-carboxamide

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Reaction Steps

1-methyl-1H-indole-3-carbonyl chloride (16.3 mmol), prepared in step 1 of Example 9, in 60 mL of methylene chloride was added under nitrogen dropwise over 15 minutes to a solution of the HCl salt of N-benzyl-N-[(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methyl]amine (5.0 g, 11.9 mmol), prepared in step 2 of Example 11, and triethylamine (4.6 mL, 33 mmol) in 100 mL of methylene chloride at room temperature. After the addition the reaction was stirred at room temperature for 16 h. The reaction was extracted with 1 N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give N-benzyl-N-[(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methyl]-1-methyl-1H-indole-3-carboxamide (6.1 g, 95%) as a white solid, MS (ESI) m/z 539 [M+H]+. Elemental Analysis for C31H27BrN2O2: Calc'd: C, 69.02; H, 5.04; N, 5.19; Found: C, 68.55; H, 5.32; N, 4.99.

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