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

HRID 490414

Reaction equation

HRID 490414 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 99:1 v/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-625b4f05c3b14382a04b4f5cd7b3a76e
Source dataset
uspto-grants-2009_05
Patent number
US07528157B2

Linked notes

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