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

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

Reactant 2

HCID 8857Ethyl Acetate

HCID 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

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

Sources & evidence

ORD record: ord-dd3df5976fb640cbaad59042b33b9d69
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07534793B2

Reaction notes

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