Methyl iodide → HCID 22327215, compound

HRID 495396Notes

Reaction equation

HRID 495396 reaction equation
IC.[Cl:3][C:4]1[C:5]([O:14][NH:15][C:16]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)=[O:17])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.[CH3:28]C(C)([O-])C.[K+]>>[Cl:3][C:4]1[C:5]([O:14][N:15]([CH3:28])[C:16]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)=[O:17])=[N:6][CH:7]=[C:8]([C:10]([F:11])([F:13])[F:12])[CH:9]=1

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 22327216HCID 22327216, compound2×HCID 23665647Potassium tert-butoxide

Product 1

HCID 22327215HCID 22327215, compound

Procedure

Iodomethane (0.82 g) was added to a stirred solution of the product from Example 13 (Compound 1012) (1.93 g) and potassium tert-butoxide (0.61 g) in tetahydrofuran (50 ml). The reaction mixture was stirred for 48 hours. The solvent was evaporated and the residue partitioned between ethyl acetate and saturated aqueous ammonium chloride. The aqueous layer was separated and extracted with 3 portions of ethyl acetate. The combined organic phases were dried, filtered and evaporated to give a residue which was purified by silica gel chromatography (ethyl acetate/petrol) to give the title compound, m/z (EI) 380 (M+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate and saturated aqueous ammonium chloride
  3. customThe aqueous layer was separated
  4. extractionextracted with 3 portions of ethyl acetate
  5. customThe combined organic phases were dried
  6. filtrationfiltered
  7. customevaporated
  8. customto give a residue which
  9. customwas purified by silica gel chromatography (ethyl acetate/petrol)

Sources & evidence

ORD record
ord-696a9c2339c14da3a08a288b722d7bea
Source dataset
uspto-grants-2005_09
Patent number
US06939882B1

Reaction notes

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