Ethyl 3-(3-fluoro-2-methylphenyl)-2-azidopropenoate → ethyl 5-fluoro-4-methyl-1H-indole-2-carboxylate

HRID 355709Notes

Reaction equation

HRID 355709 reaction equation
[F:1][C:2]1[C:3]([CH3:18])=[C:4]([CH:8]=[C:9]([N:15]=[N+]=[N-])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1>CC1C=CC=CC=1C>[F:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:5](=[CH:6][CH:7]=1)[NH:15][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8]2

Participants

3

Reactant 1

HCID 54359158Ethyl 3-(3-fluoro-2-methylphenyl)-2-azidopropenoate

Product 1

HCID 21714299ethyl 5-fluoro-4-methyl-1H-indole-2-carboxylateYield 40.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A solution of ethyl 3-(3-fluoro-2-methylphenyl)-2-azidopropenoate (10.0 g, 40.1 mmol) in o-xylene (100 ml) was slowly added dropwise in o-xylene (500 ml) at a temperature of 110° C. under stirring. The mixture was stirred at 120°-122° C. for 5 hours and the solvent was distilled off under reduced pressure. The residue obtained was recrystallized from isopropylalcohol (60 ml) to give 3.58 g of ethyl 5-fluoro-4-methyl-1H-indole-2-carboxylate.

Workup

  1. stirringThe mixture was stirred at 120°-122° C. for 5 hours
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue obtained
  4. customwas recrystallized from isopropylalcohol (60 ml)

Sources & evidence

ORD record
ord-43abf55d5ee645ea9fc25c40bbbffde8
Source dataset
uspto-grants-1998_11
Patent number
US05834454

Reaction notes

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