Methyl iodide → HCID 57421223, compound

HRID 1097866Notes

Reaction equation

HRID 1097866 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:22])[C:10]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)([OH:15])[C:11]([F:14])([F:13])[F:12].[H-].[Na+].I[CH3:26]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH3:22])[C:10]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)([O:15][CH3:26])[C:11]([F:12])([F:13])[F:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25253050HCID 25253050, compound2×

Product 1

HCID 57421223HCID 57421223, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared from 3-(2,4-dichloro-phenyl)-1,1,1-trifluoro-2-pyridin-4-yl-butan-2-ol (Example 11) by O-methylation: 3-(2,4-dichloro-phenyl)-1,1,1-trifluoro-2-pyridin-4-yl-butan-2-ol (45 mg) was dissolved in dry DMF (4 mL) under argon at room temperature. To the mixture was added sodium hydride (8.4 mg, 50% in mineral oil) and the mixture was allowed to stir for 30 minutes. Iodomethane (22 mg, 0.01 mL) was added and stirring was continued for 1 hour at room temperature. The mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (20 g silica gel, gradient of ethyl acetate in heptane (10 to 40%) to give the desired material as light yellow oil (28 mg). MS (m/e)=364.1 [MH+].

Workup

  1. stirringstirring
  2. waitwas continued for 1 hour at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography (20 g silica gel, gradient of ethyl acetate in heptane (10 to 40%)

Sources & evidence

ORD record
ord-b2b74d212f0c4d769f9c7acccf2fc852
Source dataset
uspto-grants-2012_03
Patent number
US08143280B2

Reaction notes

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