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

HRID 493489Notes

Reaction equation

HRID 493489 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]([CH3:34])[C:22]([C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH3:33])[CH:25]=3)=[O:23])=[CH:16][CH:15]=2)[CH:9]=[CH:10][C:11]=1[O:12]C.C(=O)=O.CC(C)=O.O>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][N:21]([CH3:34])[C:22]([C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH3:33])[CH:25]=3)=[O:23])=[CH:16][CH:15]=2)[CH:9]=[CH:10][C:11]=1[OH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 18522661Acetone cardice2×HCID 68860765N-[(3'-bromo-4'-methoxy-1,1'-biphenyl-4-yl)methyl]-N,1-dimethyl-1H-indole-3-carboxamide

Product 1

HCID 68860608N-[(3'-bromo-4'-hydroxy-1,1'-biphenyl-4-yl)methyl]-N,1-dimethyl-1H-indole-3-carboxamideYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Boron tribromide (44.8 mL of a 1 M solution in methylene chloride; 44 mmol) was added under nitrogen dropwise over 30 minutes to a solution of N-[(3′-bromo-4′-methoxy-1,1′-biphenyl-4-yl)methyl]-N,1-dimethyl-1H-indole-3-carboxamide (6.8 g, 14.7 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 60 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 N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-N,1-dimethyl-1H-indole-3-carboxamide (4.7 g, 71%) as a solid, mp 237-239° C. Elemental Analysis for C24H21BrN2O2. Calc'd: C, 64.15; H, 4.71; N, 6.23. Found: C, 62.15; H, 4.63; N, 5.97.

Workup

  1. customwas replaced with an ice bath
  2. customThe reaction was then partitioned between additional amounts of methylene chloride and water
  3. customThe aqueous layer was separated
  4. extractionextracted three times with methylene chloride
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e75810489b0d4260843128c23e2789e1
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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