Ethyl 3-(4-benzyloxy-2-chlorophenyl)-2-azidopropenoate → Ethyl 6-(benzyloxy)-4-chloro-1H-indole-2-carboxylate

HRID 564983Notes

Reaction equation

HRID 564983 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[C:16]([N:22]=[N+]=[N-])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:11]([Cl:25])[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:14]=[C:13]2[C:12]([CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[NH:22]2)=[C:11]([Cl:25])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 53783165Ethyl 3-(4-benzyloxy-2-chlorophenyl)-2-azidopropenoate

Product 1

HCID 21714295Ethyl 6-(benzyloxy)-4-chloro-1H-indole-2-carboxylateYield 89.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4.50 g (12.6 mmols) of ethyl 3-(4-benzyloxy-2-chlorophenyl)-2-azidopropenoate in 100 ml of toluene was refluxed for 3 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 3.73 g (89.8%) of ethyl 6-benzyloxy-4-chloro-2-indolecarboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-fc15a2e7ec854d03a383d16b207aaa66
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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