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

HRID 493501Notes

Reaction equation

HRID 493501 reaction equation
B(Br)(Br)Br.[CH2:5]([N:12]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38]C)=[C:34]([Br:40])[CH:33]=2)=[CH:28][CH:27]=1)[C:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH3:24])[CH:16]=1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)=O.CC(C)=O.O>C(Cl)Cl>[CH2:5]([N:12]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([Br:40])[CH:33]=2)=[CH:28][CH:27]=1)[C:13]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH3:24])[CH:16]=1)=[O:14])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 18522661Acetone cardice2×HCID 68860591N-benzyl-N-[(3'-bromo-4'-methoxy-1,1'-biphenyl-4-yl)methyl]-1-methyl-1H-indole-3-carboxamide

Product 1

HCID 68862509N-benzyl-N-[(3'-bromo-4'-hydroxy-1,1'-biphenyl-4-yl)methyl]-1-methyl-1H-indole-3-carboxamideYield 78.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (22.0 mL of a 1 M solution in methylene chloride; 22.0 mmol) was added under nitrogen dropwise over 30 minutes to a solution of N-benzyl-N-[(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methyl]-1-methyl-1H-indole-3-carboxamide (4.3 g, 7.97 mmol), prepared in the previous step, in 150 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 continued for 3 h. At ice bath temperature water (100 mL) was added dropwise. The aqueous layer was separated and extracted two times with methylene chloride. The extracts were combined, extracted with saturated NaCl, dried (MgSO4) and the solvent removed under reduced pressure to give N-benzyl-N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-1-methyl-1H-indole-3-carboxamide (3.3 g, 76%) as a white solid, MS (ESI) m/z 525 [M+H]+. Elemental Analysis for C30H25BrN2O2: Calc'd: C, 68.58; H, 4.80; N, 5.33; Found: C, 67.54; H, 4.92; N, 5.17.

Workup

  1. customwas replaced with an ice bath
  2. customThe aqueous layer was separated
  3. extractionextracted two times with methylene chloride
  4. extractionextracted with saturated NaCl
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-f235112a8f84412bada20de5350b687d
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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