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

HRID 2104347Notes

Reaction equation

HRID 2104347 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]([N:14]=[N+]=[N-])=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([Cl:13])[CH:7]=1>C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]([C:4]1[NH:14][C:11]2[C:6]([CH:5]=1)=[CH:7][C:8]([Cl:13])=[C:9]([F:12])[CH:10]=2)=[O:17]

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 3-chloro-4-fluoro-α-azidocinnamic acid methyl ester (Japanese Patent Application Laid-Open (kokai). No. 7-149723) (1.85 g) and xylene (140 mL) was heated under reflux for 1 hour, and the solvent was distilled away. The residue was purified by silica gel column chromatography (methylene chloride), to thereby give the title compound (491 mg).

Workup

  1. temperatureunder reflux for 1 hour
  2. distillationthe solvent was distilled away
  3. customThe residue was purified by silica gel column chromatography (methylene chloride)

Sources & evidence

ORD record
ord-1ceb747a40af4beb8470509624dcb778
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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