Methyl 3-chloro-4-fluoro-alpha-azidocinnamate → Methyl 5-chloro-6-fluoro-1H-indole-2-carboxylate
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]2Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
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
- temperatureunder reflux for 1 hour
- distillationthe solvent was then distilled off
- customThe residue was purified by column chromatography on silica gel (methylene chloride)
Sources & evidence
- ORD record
- ord-236c3c0a2fbd432f872306dece760f78
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07342014B2
Reaction notes
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