Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Cyanide | HCID 9032 | — |
| Reactant | HCID 69020222 | HCID 69020222 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 69022714 | HCID 69022714 | 90% |
Reaction Steps
Dissolve 5-bromo-3-(4-bromo-phenyl)-4-cyano-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (205 mg, 0.500 mmol, prepared in example E-265) in DMSO (2.5 mL). Add potassium cyanide (325 mg, 5.0 mmol) to the mixture. Heat the mixture at 80° C. for 16 h. Add H2O (30 mL) and methylene chloride (30 mL) into the reaction mixture. Extract with H2O (5×30 mL). Combine the organic layers, dry over magnesium sulfate, filter, and concentrate under reduced pressure. Purify by flash chromatography (elution with 33% Et2O in hexanes) to provide the title compound (161 mg, 0.450 mmol, 90%). Mass spectrum (m/e): 375.0 (M+18). Rf=0.2 (50% Et2O in hexanes).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07625932B2 |
|---|
| Source dataset | uspto-grants-2009_12 |
|---|
| ORD ID | ord-d707e26f577248f6a2e6bca647224c7b |
|---|
| Source note | uspto-grants-2009_12 |
|---|