Potassium Carbonate → HCID 68860684, compound

HRID 493482Notes

Reaction equation

HRID 493482 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH3:32])[C:17]([C:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[O:21][C:20]=3[CH2:28][CH2:29][CH2:30][CH3:31])=[O:18])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:34][C:35]#[N:36].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][N:16]([CH3:32])[C:17]([C:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[O:21][C:20]=3[CH2:28][CH2:29][CH2:30][CH3:31])=[O:18])=[CH:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:34][C:35]#[N:36]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 68861339HCID 68861339, compound

Product 1

HCID 68860684HCID 68860684, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-2-butyl-N-methyl-1-benzofuran-3-carboxamide (1.60 g, 3.25 mmol), prepared in the previous step, bromoacetonitrile (272 μL, 3.90 mmol) and potassium carbonate (2.25 g, 16.3 mmol) in 25 mL of DMF was stirred under nitrogen at room temperature for 23 h. 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}-2-butyl-N-methyl-1-benzofuran-3-carboxamide (1.65 g, 95%) as a brown foam, MS (ESI) m/z 531 [M+H]+. Elemental Analysis for C29H27BrN2O3. Calc'd: C, 65.54; H, 5.12; N, 5.27. Found: C, 65.37; H, 5.14; N, 5.21.

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-c447f2ff730c4f6080003a2f0819803b
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

Loading…