Dimethylformamide → HCID 58386652, compound

HRID 74541Notes

Reaction equation

HRID 74541 reaction equation
C(N1[C:12]2[C:7](=[C:8]([F:14])[C:9]([F:13])=[CH:10][CH:11]=2)[CH2:6]C1=O)(=O)C.[H-].[Na+].I[CH3:19].[CH3:20][N:21]([CH:23]=[O:24])C>>[F:13][C:9]1[C:8]([F:14])=[CH:7][CH:6]=[C:20]2[C:10]=1[C:11]([CH3:12])([CH3:19])[C:23](=[O:24])[NH:21]2

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58386747HCID 58386747, compound

Product 1

HCID 58386652HCID 58386652, compound

Procedure

0.50 g (2.4 mmol) 1-acetyl-4,5-difluoro-1,3-dihydro-indol-2-one were placed in 10 mL DMF under argon. 0.22 g (5.1 mmol) sodium hydride (55%) were added at 0° C. and the reaction mixture was stirred for 1 h. Then 0.32 mL (5.1 mmol) iodomethane were added dropwise. The reaction mixture was stirred overnight at RT, poured onto water and extracted with EtOAc. The organic phase was dried, filtered and concentrated to dryness by rotary evaporation. The residue was purified by HPLC. The product-containing fractions were combined and concentrated to dryness by rotary evaporation.

Workup

  1. stirringThe reaction mixture was stirred overnight at RT
  2. additionpoured onto water
  3. extractionextracted with EtOAc
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated to dryness by rotary evaporation
  7. customThe residue was purified by HPLC
  8. concentrationconcentrated to dryness by rotary evaporation

Sources & evidence

ORD record
ord-0e4565496f7944c39d13adfff8d6afd9
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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