Potassium Carbonate → N-benzyl-N-{[3'-bromo-4'-(cyanomethoxy)-1,1'-biphenyl-4-yl]methyl}-1-methyl-1H-indole-3-carboxamide

HRID 493502Notes

Reaction equation

HRID 493502 reaction equation
[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([Br:35])[CH:29]=2)=[CH:24][CH:23]=1)[C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH3:20])[CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:37][C:38]#[N:39].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([N:8]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:37][C:38]#[N:39])=[C:30]([Br:35])[CH:29]=2)=[CH:24][CH:23]=1)[C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH3:20])[CH:12]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68862509N-benzyl-N-[(3'-bromo-4'-hydroxy-1,1'-biphenyl-4-yl)methyl]-1-methyl-1H-indole-3-carboxamide

Product 1

HCID 68862634N-benzyl-N-{[3'-bromo-4'-(cyanomethoxy)-1,1'-biphenyl-4-yl]methyl}-1-methyl-1H-indole-3-carboxamideYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-benzyl-N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-1-methyl-1H-indole-3-carboxamide (1.5 g, 2.85 mmol), prepared in the previous step, bromoacetonitrile (240 μL, 3.44 mmol) and potassium carbonate (1.95 g, 14.1 mmol) in 75 mL of DMF was stirred under nitrogen at room temperature for 23 h. The reaction was partitioned between methylene chloride and water. The organic layer was separated, extracted multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give N-benzyl-N-{[3′-bromo-4′-(cyanomethoxy)-1,1′-biphenyl-4-yl]methyl}-1-methyl-1H-indole-3-carboxamide (1.2 g, 75%) as a white solid, MS (ESI) m/z 564 [M+H]+. Elemental Analysis for C32H26BrN3O2: Calc'd: C, 68.09; H, 4.64; N, 7.44; Found: C, 66.78; H, 4.68; N, 7.19.

Workup

  1. customThe reaction was partitioned between methylene chloride and water
  2. customThe organic layer was separated
  3. extractionextracted multiple times with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ed64db21eece48d9ab826a7757ea41cd
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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