Methyl iodide → HCID 66831368, compound

HRID 405995Notes

Reaction equation

HRID 405995 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:20])[CH:16]=3)[NH:11][C:10]=2[CH2:21][CH3:22])[CH:5]=[C:6]([F:8])[CH:7]=1.[H-].[Na+].[CH3:25]I>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:20])[CH:16]=3)[N:11]([CH3:25])[C:10]=2[CH2:21][CH3:22])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66831365HCID 66831365, compound

Product 1

HCID 66831368HCID 66831368, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-(3,5-difluorophenyl)-2-ethyl-6-fluoroquinolin-4(1H)-one (280 mg, 0.9 mmol) in DMF (5 mL) was treated with NaH (60%, 1.5 eq, 55.3 mg). After 30 min, MeI (0.12 mL, 2.0 eq) was added dropwise and the reaction mixture was stirred at rt overnight before quenching with water. The reaction mixture was extracted with EtOAc (5 mL×2). The organic layers were combined washed with water, brine, dried, concd and purified by column chromatography on silica gel (EtOAc/hexane, 1/2) to give 3-(3,5-difluorophenyl)-2-ethyl-6-fluoro-1-methylquinolin-4(1H)-one as a white solid. Mass Spectrum (ESI) m/e=318 (M+1).

Workup

  1. custombefore quenching with water
  2. extractionThe reaction mixture was extracted with EtOAc (5 mL×2)
  3. washThe organic layers were combined washed with water, brine
  4. customdried
  5. custompurified by column chromatography on silica gel (EtOAc/hexane, 1/2)

Sources & evidence

ORD record
ord-f50eb17aa3334d78ab3b603c08c8e545
Source dataset
uspto-grants-2014_06
Patent number
US08754089B2

Reaction notes

Loading…