Methyl iodide → HCID 67229253, compound

HRID 1785566Notes

Reaction equation

HRID 1785566 reaction equation
[Si:1]([O:8][CH:9]1[CH2:18][C:17]2[C:16]([NH:19][C:20]3[O:21][C:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)=[CH:23][N:24]=3)=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Na+].IC.[C:39](OCC)(=O)C>CN(C)C=O>[Si:1]([O:8][CH:9]1[CH2:18][C:17]2[C:16]([N:19]([CH3:39])[C:20]3[O:21][C:22]([C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][CH:26]=4)=[CH:23][N:24]=3)=[CH:15][CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 67228537HCID 67228537, compound

Product 1

HCID 67229253HCID 67229253, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product of Example 18D (300 mg, 0.615 mmol) in 5 mL N,N-dimethylformamide was treated with NaH (60% dispersion, 32 mg, 0.8 mmol) at rt. After stirring for 5 minutes, iodomethane (0.15 mL, 2.4 mmol) was added. The reaction was stirred at rt for 24 h, then it was poured into ethyl acetate and washed several times with water and once with brine. The organic layer was dried over Na2SO4 and was concentrated. The concentrate was purified on silica gel, eluting with 5% ethyl acetate-hexane and afforded the title compound as a brown oil (56 mg, 18%).

Workup

  1. stirringThe reaction was stirred at rt for 24 h
  2. washwashed several times with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationwas concentrated
  5. customThe concentrate was purified on silica gel
  6. washeluting with 5% ethyl acetate-hexane

Sources & evidence

ORD record
ord-c31e6070c6924d6d88a783bf76eea8cc
Source dataset
uspto-grants-2009_03
Patent number
US07504520B2

Reaction notes

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