Potassium Carbonate → HCID 68861317, compound

HRID 493498Notes

Reaction equation

HRID 493498 reaction equation
[CH2:1]([N:8]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[C:33]([Br:38])[CH:32]=2)=[CH:27][CH:26]=1)[C:9]([C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]=1[CH2:20][CH2:21][CH2:22][CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:40][C:41]#[N:42].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([N:8]([CH2:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:40][C:41]#[N:42])=[C:33]([Br:38])[CH:32]=2)=[CH:29][CH:30]=1)[C:9]([C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]=1[CH2:20][CH2:21][CH2:22][CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68859917HCID 68859917, compound

Product 1

HCID 68861317HCID 68861317, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-benzyl-N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-2-butyl-1-benzofuran-3-carboxamide (1.5 g, 2.64 mmol), prepared in the previous step, bromoacetonitrile (220 μL, 3.16 mmol) and potassium carbonate (1.862 g, 13.5 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. If an emulsion forms saturated NaCl can be added to separate it. 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}-2-butyl-1-benzofuran-3-carboxamide (1.1 g, 69%) as a yellow oily solid, MS (ESI) m/z 607 [M+H]+. Elemental Analysis for C35H31BrN2O3: Calc'd: C, 69.19; H, 5.14; N, 4.61; Found: C, 67.76; H, 5.44; N, 4.29

Workup

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

Sources & evidence

ORD record
ord-af42ba65c7ac4696bbf4ad470a608240
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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