Methyl 3-chloro-4-fluoro-alpha-azidocinnamate → Methyl 5-chloro-6-fluoro-1H-indole-2-carboxylate

HRID 459459Notes

Reaction equation

HRID 459459 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][C:16]=1[F:17])[CH:5]=[C:6]([N:11]=[N+]=[N-])[C:7]([O:9][CH3:10])=[O:8]>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][C:16]=1[F:17])[NH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5]2

Participants

3

Reactant 1

HCID 54554773Methyl 3-chloro-4-fluoro-alpha-azidocinnamate

Product 1

HCID 18986230Methyl 5-chloro-6-fluoro-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of methyl 3-chloro-4-fluoro-α-azidocinnamate (Japanese Patent Application Laid-Open No. 149723/1995) (1.85 g) and xylene (140 ml) was heated under reflux for 1 hour, and the solvent was then distilled off. The residue was purified by column chromatography on silica gel (dichloromethane) to obtain the title compound (491 mg) as colorless powder.

Workup

  1. temperatureunder reflux for 1 hour
  2. distillationthe solvent was then distilled off
  3. customThe residue was purified by column chromatography on silica gel (dichloromethane)

Sources & evidence

ORD record
ord-9219bfba367a4a4f9fe7313f3d52e2b0
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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