Methyl iodide → HCID 11503833, compound

HRID 1173476Notes

Reaction equation

HRID 1173476 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:25][C:26]([F:29])([F:28])[F:27])[CH2:12][CH2:13][S:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:24])[CH3:23])=[CH:17][CH:16]=2)=[CH:7][C:6]=1[C:30]([F:33])([F:32])[F:31])#[N:4].I[CH3:35]>CN(C=O)C>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]([CH2:25][C:26]([F:29])([F:27])[F:28])[CH2:12][CH2:13][S:14][C:15]2[CH:16]=[CH:17][C:18]([N:21]([CH3:35])[C:22](=[O:24])[CH3:23])=[CH:19][CH:20]=2)=[CH:7][C:6]=1[C:30]([F:31])([F:33])[F:32])#[N:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11712326HCID 11712326, compound

Product 1

HCID 11503833HCID 11503833, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% in oil, 0.003 g, 0.075 mmol) was added to a solution of N-[4-({2-[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]ethyl}thio)phenyl]acetamide (0.026 g, 0.056 mmol) in DMF (2 mL) under N2. After 5 min, iodomethane (0.009 g, 0.063 mmol) was added and stirred at rt for 30 min. The mixture was partitioned between Et2O and water. The organic phase was washed with water and brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel chromatography (5-80% EtOAc/hexanes gradient) to give the title compound (0.018 mg, 66% yield): MS (ES) m/z 476 (M+1).

Workup

  1. customThe mixture was partitioned between Et2O and water
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (5-80% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-af7956e30df84523b7d319a1629dc1b0
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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