5-Chloro-6-fluoro-1H-indole-2-carboxylic acid → 5-chloro-6-fluoro-1H-indole

HRID 2396852Notes

Reaction equation

HRID 2396852 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6](C(O)=O)=[CH:5]2.[Cl:15][C:16]1[C:17]([F:28])=[CH:18][CH:19]=[C:20]2[C:24]=1[NH:23][C:22](C(O)=O)=[CH:21]2>C1(OC2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH:6]=[CH:5]2.[Cl:15][C:16]1[C:17]([F:28])=[CH:18][CH:19]=[C:20]2[C:24]=1[NH:23][CH:22]=[CH:21]2

Participants

5

Reactant 2

HCID 189862355-Chloro-6-fluoro-1H-indole-2-carboxylic acidHCID 189862747-Chloro-6-fluoro-1H-indole-2-carboxylic acid

Product 2

HCID 27736475-chloro-6-fluoro-1H-indoleYield 39%HCID 189862317-chloro-6-fluoro-1H-indoleYield 14%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A suspension of 1.92 g of an almost 1:1 mixture of 5-chloro-6-fluoro-indole-2-carboxylic acid and 7-chloro-6-fluoro-indole-2-carboxylic acid in 45 ml of diphenyl ether was stirred at 260° for 4 hours. The reaction mixture was chromatographed over 100 g of silica gel with hexane and hexane-toluene (3:1). There were obtained 0.6 g (39%) of 5-chloro-6-fluoroindole as light brown crystals with m.p. 88°-90° and 0.22 g (14%) of 7-chloro-6-fluoroindole as a dark brown oil.

Workup

  1. customThe reaction mixture was chromatographed over 100 g of silica gel with hexane and hexane-toluene (3:1)

Sources & evidence

ORD record
ord-820f1cf2ff544dbb8ab96d558c92fdef
Source dataset
uspto-grants-1996_02
Patent number
US05494928

Reaction notes

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