Methyl iodide → HCID 22042635, compound

HRID 2053681Notes

Reaction equation

HRID 2053681 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]([C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH3:34])[S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])=[CH:20][CH:19]=1)([OH:17])[C:13]([F:16])([F:15])[F:14].I[CH3:36]>CN(C=O)C>[CH3:3][O:4][CH2:5][CH2:6][N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]([C:18]1[CH:23]=[CH:22][C:21]([N:24]([CH3:34])[S:25]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)(=[O:27])=[O:26])=[CH:20][CH:19]=1)([O:17][CH3:36])[C:13]([F:15])([F:14])[F:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22042567HCID 22042567, compound

Product 1

HCID 22042635HCID 22042635, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 3.8 mg of NaH (0.10 mmol) in 3 mL of DMF at 0° C. was added 32 mg of N-(4-{1-[1-(2-methoxyethyl)-1H-pyrrol-2-yl]-2,2,2-trifluoro-1-hydroxyethyl}-phenyl)-N-methyl-benzenesulfonamide (Example 79, 0.068 mmol) and the reaction mixture was stirred at 0° C. for 35 min. 6 μL of iodomethane (0.089 mmol) was added and the reaction mixture allowed to warm to room temperature and stirred for 2.5 h. The reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:EtOAc, 9:1) to give the title compound.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 2.5 h
  3. customThe reaction was quenched by the addition of a saturated aqueous solution of ammonium chloride
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by chromatography (silica, hexanes:EtOAc, 9:1)

Sources & evidence

ORD record
ord-d744d1e6072644f3bf1c13ca1de405a5
Source dataset
uspto-grants-2008_02
Patent number
US07326812B2

Reaction notes

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