Methyl iodide → 3-(3,4-Dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-5-fluoro-benzonitrile

HRID 469357Notes

Reaction equation

HRID 469357 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([C:12]([C:14]2[CH:23]=[C:22]([CH3:24])[C:17]3[NH:18][C:19](=[O:21])[O:20][C:16]=3[CH:15]=2)=[O:13])[CH:11]=1)[C:7]#[N:8].I[CH3:26]>CN(C=O)C>[CH3:26][N:18]1[C:17]2[C:22]([CH3:24])=[CH:23][C:14]([C:12]([C:10]3[CH:9]=[C:6]([CH:5]=[C:4]([F:3])[CH:11]=3)[C:7]#[N:8])=[O:13])=[CH:15][C:16]=2[O:20][C:19]1=[O:21]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 581811573-Fluoro-5-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-benzonitrile

Product 1

HCID 581811493-(3,4-Dimethyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-5-fluoro-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.161 g (3.70 mmol) sodium hydride (55%, suspension in mineral oil) were added to 1.00 g (3.38 mmol) 3-fluoro-5-(4-methyl-2-oxo-2,3-dihydro-benzoxazole-6-carbonyl)-benzonitrile in 5 mL DMF at RT and stirred for 30 min at RT. Then 0.317 mL (5.00 mmol) iodomethane were added and the mixture was stirred for 1 h at RT. Then a further 0.1 mL iodomethane were added and stirring was continued at RT. After dilution with ice water the aqueous phase was extracted with EtOAc. The organic phase was washed with water, dried on sodium sulphate, filtered and evaporated down i. vac. The residue was purified by flash chromatography. The fractions containing the product were combined, evaporated down and dried i. vac.

Workup

  1. stirringthe mixture was stirred for 1 h at RT
  2. stirringstirring
  3. customwas continued at RT
  4. extractionAfter dilution with ice water the aqueous phase was extracted with EtOAc
  5. washThe organic phase was washed with water
  6. customdried on sodium sulphate
  7. filtrationfiltered
  8. customevaporated down i
  9. customThe residue was purified by flash chromatography
  10. additionThe fractions containing the product
  11. customevaporated down
  12. customdried i

Sources & evidence

ORD record
ord-bc8739cbd97641389c7aca8abb3c224d
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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