Methyl 4-benzyloxy-alpha-azidocinnamate → methyl 6-(benzyloxy)-1H-indole-2-carboxylate

HRID 361862Notes

Reaction equation

HRID 361862 reaction equation
[CH2:1]([O:8][C:9]1[CH:23]=[CH:22][C:12]([CH:13]=[C:14]([N:19]=[N+]=[N-])[C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:23]=[C:22]2[C:12]([CH:13]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[NH:19]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 54271879Methyl 4-benzyloxy-alpha-azidocinnamate

Product 1

HCID 4715068methyl 6-(benzyloxy)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl 4-benzyloxy-α-azidocinnamate (EXAMPLE 246, 5.8 g) is dissolved in 376 ml of toluene and the reaction is heated to reflux for 1 hr. Then the reaction is cooled, concentrated under reduced pressure and the solids are recrystallized from ethyl acetate/hexane to provide the title compound.

Workup

  1. temperaturethe reaction is heated
  2. temperatureto reflux for 1 hr
  3. temperatureThen the reaction is cooled
  4. concentrationconcentrated under reduced pressure
  5. customthe solids are recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-4b7ec0b24fde4a0f889878d01e358f80
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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