HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Ethyl 1-{[4-(methyloxy)phenyl]methyl}-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | methyl 2-{2-amino-1-[(ethyloxy)carbonyl]ethenyl}-1-{[4-(methyloxy)phenyl]methyl}-1H-pyrrole-3-carboxylate | HCID 68867423 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Ethyl 1-{[4-(methyloxy)phenyl]methyl}-4-oxo-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-7-carboxylate | HCID 57840819 | 537.9% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07589206B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-d614094f94f849e98be4e785ceb91649 |
| Source note | uspto-grants-2009_09 |