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

HRID 902831Notes

Reaction equation

HRID 902831 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 (methylene chloride) to obtain the title compound (491 mg).

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 (methylene chloride)

Sources & evidence

ORD record
ord-9b87abf9efaf41a3b9b388d7b110dd32
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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