Dimethylformamide → 5-(4-Fluorophenyl)-2-methoxy-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyridine

HRID 234708Notes

Reaction equation

HRID 234708 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[CH:10][C:11](=[O:18])[NH:12][C:13]=2[C:14]([F:17])([F:16])[F:15])=[CH:4][CH:3]=1.[C:29](=O)([O-])[O-].[K+].[K+].IC.CN(C=O)C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][CH:20]=3)=[CH:10][C:11]([O:18][CH3:29])=[N:12][C:13]=2[C:14]([F:15])([F:17])[F:16])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 233552585-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)-2-oxo-pyridine

Product 1

HCID 99321855-(4-Fluorophenyl)-2-methoxy-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyridineYield 102.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.16 g (0.39 mMol) of the sulfone of Step 5, 0.2 g of potassium carbonate and 4.0 g of iodomethane, and 5 mL of DMF was stirred for 3 hours, poured into water and extracted with ether. The ether extract was washed with brine, dried over MgSO4 and filtered through silica gel. The filtrate was concentrated in vacuo and the residue was crystallized from hexane to give 5-(4-fluorophenyl)-2-methoxy-4-[4-(methylsulfonyl)phenyl]-6-(trifluoromethyl)pyridine as a white solid (0.17 g): mp 166.5°-168 ° C.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through silica gel
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue was crystallized from hexane

Sources & evidence

ORD record
ord-1840e65b8616419dab8bb83b89785a3d
Source dataset
uspto-grants-1997_01
Patent number
US05596008

Reaction notes

Loading…