Ethyl Acetate → ethyl 4,7-difluoro-1H-indole-2-carboxylate

HRID 493123Notes

Reaction equation

HRID 493123 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:12]=[O:13])[NH:6]2.[C:14](OCC)(=[O:16])[CH3:15]>>[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:16][CH2:14][CH3:15])=[O:13])[NH:6]2

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 22281717HCID 22281717, compound

Product 1

HCID 22281774ethyl 4,7-difluoro-1H-indole-2-carboxylate

Procedure

The cooled mixture was dissolved in ethyl acetate, washed with sodium bicarbonate and brine, dried and evaporated. Chromatography on silica gel (1:1 dichloromethane/petrol) followed by recrystallization (dichloromethane/hexane) gave the indole ester (0.75 g). (f) 4,7-Difluoroindole-2-carboxaldehyde

Workup

  1. washwashed with sodium bicarbonate and brine
  2. customdried
  3. customevaporated
  4. customChromatography on silica gel (1:1 dichloromethane/petrol) followed by recrystallization (dichloromethane/hexane)
  5. customgave the indole ester (0.75 g)

Sources & evidence

ORD record
ord-dd3df5976fb640cbaad59042b33b9d69
Source dataset
uspto-grants-2009_05
Patent number
US07534793B2

Reaction notes

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