Methyl iodide → HCID 178429123, compound

HRID 237497Notes

Reaction equation

HRID 237497 reaction equation
[Br:1][C:2]1[C:17]([CH3:18])=[CH:16][C:5]([O:6][C@@H:7]2[CH2:10][C@H:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:8]2)=[CH:4][C:3]=1[CH3:19].[H-].[Na+].I[CH3:23]>CN(C)C(=O)C>[Br:1][C:2]1[C:17]([CH3:18])=[CH:16][C:5]([O:6][C@@H:7]2[CH2:8][C@H:9]([N:11]([CH3:23])[S:12]([CH3:15])(=[O:14])=[O:13])[CH2:10]2)=[CH:4][C:3]=1[CH3:19]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178429124HCID 178429124, compound

Product 1

HCID 178429123HCID 178429123, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

N-(cis-3-(4-bromo-3,5-dimethylphenoxy)cyclobutyl)methanesulfonamide (130 mg) and sodium hydride (16 mg) are stirred in N,N-dimethylacetamide (2 mL) for 10 minutes. Iodomethane (0.1 mL) is added and the mixture is stirred at ambient temperature overnight. After cooling to ambient temperature, the mixture is concentrated, partitioned between ethyl acetate and water. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate gradient of increasing polarity) to give the title compound. Yield: 110 mg.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe mixture is concentrated
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic phase is dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate gradient of increasing polarity)

Sources & evidence

ORD record
ord-0c6a5b9b0a664f42861be24bfd4893ce
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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