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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 733735Generated: October 27, 2026

Water → Ethyl 1-{[4-(methyloxy)phenyl]methyl}-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate

https://huagongshe.com/reaction/733735

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantDimethylformamideHCID 6228—
ReactantSodium t-butoxideHCID 23676156—
ReactantEthyl 2-{2-amino-1-[(ethyloxy)carbonyl]ethenyl}-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrole-3-carboxylateHCID 68866632—
SolventEthyl AcetateHCID 8857—
ProductEthyl 1-{[4-(methyloxy)phenyl]methyl}-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylateHCID 578408191,711.7%

Reaction Steps

A mixture of ethyl 2-{2-amino-1-[(ethyloxy)carbonyl]ethenyl}-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrole-3-carboxylate (0.2 g), sodium tert-butoxide (26 mg) and dimethylformamide (2 ml) was irradiated with microwaves at 160° C. for 8 minutes. The procedure was repeated on a 2 g and 3 g scale, the cooled solutions combined, added slowly to iced water then stirred for 25 minutes. A precipitate formed which was dissolved in ethyl acetate and washed with water. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated to afford the title compound as a white solid (3.00 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07589206B2
Source datasetuspto-grants-2009_09
ORD IDord-4d63c001cfa84b3fba30b3e0d911554a
Source noteuspto-grants-2009_09