Methanol → HCID 10207712, compound

HRID 1835309Notes

Reaction equation

HRID 1835309 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12](I)=[N:11][CH:10]=1.C(N(CC)CC)C.[CH3:41][OH:42].[C]=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)[CH:66]=[O:67]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:41][O:42][C:66]([C:12]1[CH:13]=[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[C:9]([C:8](=[O:23])[N:7]([CH2:6][C:5]2[CH:25]=[C:26]([C:28]([F:29])([F:31])[F:30])[CH:27]=[C:3]([C:2]([F:33])([F:32])[F:1])[CH:4]=2)[CH3:24])=[CH:10][N:11]=1)=[O:67]

Participants

9

Reactant 6

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 10231844N-(3,5-Bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamideHCID 178418416HCID 178418416, compound

Product 1

HCID 10207712HCID 10207712, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

A solution of 690 mg (1.19 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide, 0.33 ml (2.4 mmol) triethylamine and 1.9 ml (48 mmol) methanol in 10 ml N,N-dimethylformamide was deoxygenated by three freeze-thaw cycles. Filling the flask with carbon monoxide gas from a balloon was followed by addition of 31 mg (0.12 mmol) triphenylphosphine and 23 mg (0.102 mmol) palladium(II) acetate. The reaction mixture was stirred for 60 h under an atmosphere of carbon monoxide gas at room temperature. The mixture was diluted with water and extracted with 3 portions of tert-butyl methyl ether. The combined organic extracts were washed with water, dried with sodium sulfate and concentrated. Flash chromatography afforded 407 mg (66.8%) of the title compound as a light-yellow solid.

Workup

  1. extractionextracted with 3 portions of tert-butyl methyl ether
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8029ad542a4b4df19b9f5bda2f0f2327
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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