1H-Pyrrolo(2,3-b)pyridine → methyl 2-(1H-pyrrolo[2,3-b]pyridin-1-yl)acetate

HRID 55478

Reaction equation

HRID 55478 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[CH:5]=[CH:4]1.Br[CH2:13][C:14]([O:16][CH3:17])=[O:15]>CN(C)C=O>[N:3]1([CH2:13][C:14]([O:16][CH3:17])=[O:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 23298344methyl 2-(1H-pyrrolo[2,3-b]pyridin-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A procedure similar to that described in Preparation 12 was repeated, except that 1.90 g of sodium hydride (as a 55% by weight dispersion in mineral oil), 4.95 g of 7-azaindol, 100 ml of dimethylformamide and 4.2 ml of methyl bromoacetate were used, to give 7.70 g of the title compound having Rf=0.33 (on silica gel thin layer chromatography using a 2:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 12

Sources & evidence

ORD record
ord-00cdc0efc62042db92cba204b56a5778
Source dataset
uspto-grants-1997_04
Patent number
US05624935

Linked notes

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