Methyl iodide → HCID 91123297, compound

HRID 857353Notes

Reaction equation

HRID 857353 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:16]([CH:18]([OH:20])[CH3:19])=[CH:15][C:14]([F:21])=[CH:13][C:12]=3[N:11]3[CH2:22][CH2:23][CH:24]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:10]=23)=[CH:4][CH:3]=1.[H-].[Na+].[CH3:32]I>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:16]([CH:18]([O:20][CH3:32])[CH3:19])=[CH:15][C:14]([F:21])=[CH:13][C:12]=3[N:11]3[CH2:22][CH2:23][CH:24]([CH2:25][C:26]([O:28][CH3:29])=[O:27])[C:10]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 91424771HCID 91424771, compound

Product 1

HCID 91123297HCID 91123297, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the alcohol of Step 1 (105 mg, 0.25 mmol) in DMF (5 mL) at 0° C. was added NaH (11 mg, 0.3 mmol). The reaction mixture was stirred at 0° C. for 20 minutes and MeI (51 mg, 0.4 mmol) was added. The reaction was stirred at 0° C. for 30 minutes and quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 30% EtOAc in Hexanes to provide 90 mg of the title compound as a white solid.

Workup

  1. stirringThe reaction was stirred at 0° C. for 30 minutes
  2. customquenched with saturated aqueous NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. washeluted with 30% EtOAc in Hexanes

Sources & evidence

ORD record
ord-d536780e45de420189d869fffe0a3e9d
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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