HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylamine → 3-{4-[3-(2-Cyanophenoxy)phenyl]-2-oxo-pyrrolidin-1-yl}benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylamine | HCID 1146 | — |
| Reactant | 2-Cyanophenylboronic acid | HCID 2734610 | — |
| Reactant | 3-[4-(3-Hydroxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamide | HCID 68828378 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 3-{4-[3-(2-Cyanophenoxy)phenyl]-2-oxo-pyrrolidin-1-yl}benzamide | HCID 68832504 | 43.1% |
Reaction Steps
A mixture of 3-[4-(3-hydroxyphenyl)-2-oxo-pyrrolidin-1-yl]benzamide (30 mg), 2-cyanobenzeneboronic acid (12 mg), and copper acetate (2 eq) was created in a dry tube. The mixture was dissolved in 2 mL CH2Cl2 followed by the addition of (CH3)3N (3 eq). The mixture was stirred at r.t. for 24 h, and then diluted with 10 mL CH2Cl2. The resulting mixture was filtered and washed with NH4Cl solution, water and brine. After removal of solvent, the residue was purified by preparative LC-MS to give 14 mg of the desired product. Yield: 35%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07495016B2 |
| Source dataset | uspto-grants-2009_02 |
| ORD ID | ord-918ee949fa84431ba3d6e6c5a2a6b387 |
| Source note | uspto-grants-2009_02 |