Methyl iodide → 4-([(4'-Difluoromethoxy-biphenyl-4-yl)-methyl-amino]-methyl)-5-methyl-furan-2-carboxylic acid methyl ester

HRID 460112

Reaction equation

HRID 460112 reaction equation
IC.[C:3](=O)([O-])[O-].[K+].[K+].[CH3:9][O:10][C:11]([C:13]1[O:14][C:15]([CH3:36])=[C:16]([CH2:18][NH:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH:33]([F:35])[F:34])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH:17]=1)=[O:12]>CN(C)C=O>[CH3:9][O:10][C:11]([C:13]1[O:14][C:15]([CH3:36])=[C:16]([CH2:18][N:19]([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH:33]([F:35])[F:34])=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)[CH3:3])[CH:17]=1)=[O:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 588241804-(4'-Difluoromethoxy-biphenyl-4-ylaminomethyl)-5-methylfuran-2-carboxylic acid methyl ester

Product 1

HCID 588241664-([(4'-Difluoromethoxy-biphenyl-4-yl)-methyl-amino]-methyl)-5-methyl-furan-2-carboxylic acid methyl esterYield 63.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (91 mg, 0.64 mmoles) and potassium carbonate (88 mg, 0.64 mmoles) were added to a solution of 4-(4′-difluoromethoxy-biphenyl-4-ylaminomethyl)-5-methyl-furan-2-carboxylic acid methyl ester (170) (62 mg, 0.16 mmoles) in N,N-dimethylformamide (10 ml) and the mixture stirred at room temperature for 36 hours under an argon atmosphere. The mixture was then heated at 35° C. for 21 hours. The mixture was partitioned between dichloromethane and water, the organic phase separated and dried (MgSO4). After evaporation of the solvent, the residue was purified by flash chromatography, using cyclohexane/ethyl acetate 99:1v/v as eluent, to afford compound 175(41 mg) as a brown oil. This was used directly in part (b).

Workup

  1. temperatureThe mixture was then heated at 35° C. for 21 hours
  2. customThe mixture was partitioned between dichloromethane and water
  3. customthe organic phase separated
  4. dry with materialdried (MgSO4)
  5. customAfter evaporation of the solvent
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5f0ff8c15389453fbf901f9f893a5ad8
Source dataset
uspto-grants-2007_03
Patent number
US07196089B2

Linked notes

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