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

HRID 493490Notes

Reaction equation

HRID 493490 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH3:29])[C:17]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH3:28])[CH:20]=3)=[O:18])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:31][C:32]#[N:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH3:29])[C:17]([C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH3:28])[CH:20]=3)=[O:18])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:31][C:32]#[N:33]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68860608N-[(3'-bromo-4'-hydroxy-1,1'-biphenyl-4-yl)methyl]-N,1-dimethyl-1H-indole-3-carboxamide

Product 1

HCID 68862639N-{[3'-bromo-4'-(cyanomethoxy)-1,1'-biphenyl-4-yl]methyl}-N,1-dimethyl-1H-indole-3-carboxamideYield 68.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-N,1-dimethyl-1H-indole-3-carboxamide (4.6 g, 10.2 mmol), prepared in the previous step, bromoacetonitrile (856 μL, 12.3 mmol) and potassium carbonate (7.0 g, 50 mmol) in 75 mL of DMF was stirred under nitrogen at room temperature for 23 h (overnight). The reaction was partitioned between ethyl acetate and water. The organic layer was separated, extracted multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give N-{[3′-bromo-4′-(cyanomethoxy)-1,1′-biphenyl-4-yl]methyl}-N,1-dimethyl-1H-indole-3-carboxamide (3.4 g, 68%) as an off-white solid, mp 202-206° C. Elemental Analysis for C26H22BrN3O2. Calc'd: C, 63.94; H, 4.54; N, 8.60. Found: C, 50.59; H, 3.30; N, 8.00

Workup

  1. customThe reaction was partitioned between ethyl acetate 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-552abeb49c5b4b5c96fbb789b68765ca
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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