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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 733741Generated: 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/733741

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantDimethylformamideHCID 6228—
ReactantSodium t-butoxideHCID 23676156—
Reactantmethyl 2-{2-amino-1-[(ethyloxy)carbonyl]ethenyl}-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrole-3-carboxylateHCID 68867423—
SolventEthyl AcetateHCID 8857—
ProductEthyl 1-{[4-(methyloxy)phenyl]methyl}-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylateHCID 57840819537.9%

Reaction Steps

A mixture of methyl 2-{2-amino-1-[(ethyloxy)carbonyl]ethenyl}-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrole-3-carboxylate (2.95 g), sodium tert-butoxide (0.38 g) and dimethylformamide (20 ml) was irradiated with microwaves at 180° C. for 2.5 h. The procedure was repeated five times, 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 brown solid (14.45 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07589206B2
Source datasetuspto-grants-2009_09
ORD IDord-d614094f94f849e98be4e785ceb91649
Source noteuspto-grants-2009_09