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

HRID 546405Notes

Reaction equation

HRID 546405 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-a3e5e9f52c684f409454aa374302f0c5
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

Loading…