6-chloro-7-fluoro-1H-indole-2-carboxylic acid → 6-chloro-7-fluoro-1H-indole

HRID 844205Notes

Reaction equation

HRID 844205 reaction equation
[Cl:1][C:2]1[C:10]([F:11])=[C:9]2[C:5]([CH:6]=[C:7](C(O)=O)[NH:8]2)=[CH:4][CH:3]=1>C1(OC2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[C:10]([F:11])=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 223380796-chloro-7-fluoro-1H-indole-2-carboxylic acid

Product 1

HCID 226127456-chloro-7-fluoro-1H-indoleYield 63%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

A solution of 6-chloro-7-fluoroindole-2-carboxylic acid (2.1 g, 9.8 mmol) and diphenyl ether (30 mL) was heated under reflux for 4 h, cooled to room temperature and purified by column chromatography [SiO2; heptane-ethyl acetate (99:1 to 10:1)] to give the product (1.04 g, 63% yield) as a pale brown oil: IR νmax (Nujol)/cm−1 3460, 1573, 1490, 1446, 1201, 802 and 619; NMR δH (400 MHz, CDCl3) 6.44 (1H, brs) 7.04-7.09 (1H, m) 7.21-7.26 (1H, m) 7.30-7.34 (1H, m) and 8.40 (1H, brs).

Workup

  1. temperatureunder reflux for 4 h
  2. custompurified by column chromatography [SiO2; heptane-ethyl acetate (99:1 to 10:1)]

Sources & evidence

ORD record
ord-d3b63a6372d449c7a2c82cb9e13541c5
Source dataset
uspto-grants-2002_04
Patent number
US06380238B1

Reaction notes

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