Potassium Carbonate → HCID 131727449, compound

HRID 493483Notes

Reaction equation

HRID 493483 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]([O:37][CH3:38])=[O:36].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:38][O:37][C:35](=[O:36])[CH2:34][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][N:16]([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])[CH3:32])=[CH:13][CH:14]=2)=[CH:3][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68861339HCID 68861339, compound

Product 1

HCID 131727449HCID 131727449, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[(3′-bromo-4′-hydroxy-1,1′-biphenyl-4-yl)methyl]-2-butyl-N-methyl-1-benzofuran-3-carboxamide (1.01 g, 2.04 mmol), prepared in step 7 of Example 6, methyl bromoacetate (213 μL, 2.25 mmol) and potassium carbonate (1.41 g, 10.2 mmol) in 20 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 methyl[(3-bromo-4′-{[[(2-butyl-1-benzofuran-3-yl)carbonyl](methyl)amino]methyl}-1,1′-biphenyl-4-yl)oxy]acetate (1.07 g, 93%) as a yellow oil, MS (ESI) m/z 564 [M+H]+. Elemental Analysis for C30H30BrNO5. Calc'd: C, 63.83; H, 5.36; N, 2.48. Found: C, 63.42; H, 5.40; N, 2.39.

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-8a1a42e6cec94660ae01b5318e247cb2
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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