HCID 86591894, compound → HCID 23510061, compound

HRID 1883114Notes

Reaction equation

HRID 1883114 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[C:15](/[N:21]=[N+]=[N-])\[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=1)=[O:6])[CH:2]=[CH2:3]>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]([NH:7][C:8]1[CH:13]=[C:12]2[C:11]([CH:14]=[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:21]2)=[CH:10][CH:9]=1)=[O:6])[CH:2]=[CH2:3]

Participants

3

Reactant 1

HCID 86591894HCID 86591894, compound

Product 1

HCID 23510061HCID 23510061, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

385 mg (1.217 mmol) of ethyl (2E)-3-(4-{[(allyloxy)carbonyl]amino}phenyl)-2-azidoprop-2-enoate was dissolved in 25 mL toluene (˜0.05M solution). The mixture was heated to 80° C. for 2 h, cooled, and concentrated. Purification by column chromatography, eluting with 25% ethyl acetate/hexane provided 134 mg of ethyl 6-{[(allyloxy)carbonyl]amino}-1H-indole-2-carboxylate as a yellow solid.

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customPurification by column chromatography
  4. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d234ce3097444940b11f4aaa879a5138
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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