Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Benzoyl isocyanate | HCID 78210 | — |
| Reactant | HCID 69083084 | HCID 69083084 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 69085911 | HCID 69085911 | 93.6% |
Reaction Steps
4-[2-(3-Trifluoromethyl-phenyl)-vinyl]-pyridin-2-ylamine (193 mg, 0.73 mmol) is dissolved in DCM (7 mL) and benzoyl isocynate (215 mg, 1.46 mmol) is added. The reaction is sealed and heated at 50° C. for 16 hrs. Then the solvent is removed and to the residue are added ethanol (7 mL) and potassium carbonate (151 mg, 1.10 mmol). The mixture is heated at 80° C. for 45 min. The solvent is removed and the residue is partitioned between water (45 mL) and EtOAc (55 mL). The aqueous layer is separated and extracted with EtOAc (2×30 mL). The organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) affords 210 mg of the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08722709B2 |
|---|
| Source dataset | uspto-grants-2014_05 |
|---|
| ORD ID | ord-0b353d2c64294fde9007699ed7884b07 |
|---|
| Source note | uspto-grants-2014_05 |
|---|