Methanol → HCID 86584827, compound

HRID 1835365Notes

Reaction equation

HRID 1835365 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21](I)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:62][OH:63].[C]=O.CN(C)[CH:68]=[O:69]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:62][O:63][C:68]([C:21]1[CH:22]=[C:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[C:18]([N:16]([C:14](=[O:15])[C:13]([C:5]2[CH:4]=[C:3]([C:2]([F:35])([F:34])[F:1])[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=2)([CH3:33])[CH3:32])[CH3:17])=[CH:19][N:20]=1)=[O:69]

Participants

9

Reactant 6

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 23502817HCID 23502817, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 86584827HCID 86584827, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 100 mg (0.165 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-(6-iodo-4-o-tolyl-pyridin-3-yl)-N-methyl-isobutyramide (Example 27),0.046 ml (0.33 mmol) triethylamine, 4 mg (0.02 mmol) triphenylphosphine and 0.27 ml (6.6 mmol) methanol in 2.5 ml N,N-dimethylformamide was deoxygenated in a glas flask by three freeze-thaw cycles. After addition of 4 mg (0.02 mmol) palladium(II) acetate under argon the flask containing the reaction mixture was transferred to an autoclave which was sealed and pressurized with carbon monoxide gas to 60 bar. After stirring at 50° C. for 16 h the mixture was diluted with water and extracted with three portions of tert-butyl methyl ether. The combined organic extracts were washed with water, dried with sodium sulfate and concentrated. Flash chromatography afforded 48 mg (54%) of the title compound as an orange gum.

Workup

  1. additioncontaining the reaction mixture
  2. customwas sealed
  3. extractionextracted with three portions of tert-butyl methyl ether
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d9bce0567d0c4bf79c2b291b423a27ca
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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