Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (3-Methoxyphenyl)boronic acid | HCID 2734370 | — |
| Reactant | HCID 14529698 | HCID 14529698 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 14529703 | HCID 14529703 | 62.9% |
Reaction Steps
A solution is prepared from 339 mg of 4-(4-methoxy-3-trifluoromethanesulfonyloxyphenyl)-pyrrolidin-2-one in 9 ml of toluene and 4 ml of ethanol and stirred for 5 minutes under argon at room temperature with 38 mg of tetrakis(triphenylphosphine) palladium(0). After addition of 172 mg of m-methoxyphenylboronic acid and 1.3 ml of 2-molar sodium carbonate solution, the mixture is heated to 90° C. for 4 hours. After adding ethyl acetate and water, the organic phase is separated, washed neutral with saturated sodium chloride solution, dried over sodium sulfate, and concentrated. Recrystallization from alcohol/ethyl acetate/petroleum ether (40°-60° C.) yields 187 mg of compound having a melting point of 137°-139° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05064854 |
|---|
| Source dataset | uspto-grants-1991_11 |
|---|
| ORD ID | ord-dc012e7d575447878d7e7c1842fca8b3 |
|---|
| Source note | uspto-grants-1991_11 |
|---|