Methyl iodide → HCID 57421223, compound

HRID 333767Notes

Reaction equation

HRID 333767 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 0-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-938d2609c01a4d92bbddb337cbd984ce
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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