HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 4-bromo-1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | ethyl 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylate | HCID 138486 | — |
| Reactant | 2-Bromo-N-(5-chloro-2-pyridinyl)acetamide | HCID 3421110 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-bromo-1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester | HCID 69289410 | 26.5% |
Reaction Steps
To a solution of 4-bromo-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (492 mg) in DMF (5 mL) was added Cs2CO3 (912 mg). The mixture was stirred for 30 min at RT after which 2-bromo-N-(5-chloro-pyridin-2-yl)-acetamide (499 mg) was added. Stirring was continued for 2 h at RT whereupon the mixture was filtered and concentrated. The residue was subjected to preparative HPLC(CH3CN/H2O gradient+0.05% TFA) to give 4-bromo-1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester (220 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07465806B2 |
| Source dataset | uspto-grants-2008_12 |
| ORD ID | ord-83bb7b9a59a24d1e969404f442c1a33a |
| Source note | uspto-grants-2008_12 |