Ethyl alpha-Azido-beta-(4-methoxypyrid-3-yl)-acrylate → Ethyl 4-methoxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

HRID 1445920

Reaction equation

HRID 1445920 reaction equation
[N:1]([C:4](=[CH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>CC1C=CC=CC=1C>[CH2:8]([O:7][C:5]([C:4]1[NH:1][C:12]2=[N:13][CH:14]=[CH:15][C:16]([O:17][CH3:18])=[C:11]2[CH:10]=1)=[O:6])[CH3:9]

Participants

3

Reactant 1

HCID 72796408Ethyl alpha-Azido-beta-(4-methoxypyrid-3-yl)-acrylate

Product 1

HCID 11736140Ethyl 4-methoxy-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A stirred solution of ethyl-α-azido-β-(4-methoxypyrid-3-yl)-acrylate 2 (3.7 g, 14.9 mmol) in dry o-xylene (35 mL) was heated in an oil bath at 170° C. for 25 min. During this time the contents of the flask gained brick red color. After cooling, the mixture was concentrated under high vacuum. The resultant brown residue was purified on silica gel column using 5% methanol in CH2Cl2 to give 3 as brick red solid. Mp 195-197° C.; Yield: 3.3 g, 82%; ESI MS: m/z 220.9 (M+1).

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated under high vacuum
  3. customThe resultant brown residue was purified on silica gel column
  4. customto give 3 as brick red solid

Sources & evidence

ORD record
ord-1feb00a08af34c57a4e5d752862b7d45
Source dataset
uspto-grants-2010_02
Patent number
US07666898B2

Linked notes

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