Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-(Chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole | HCID 2736622 | — |
| Reactant | HCID 86620728 | HCID 86620728 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86620731 | HCID 86620731 | 22.2% |
Reaction Steps
A mixture of 2-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 374A) (0.080 g, 0.27 mmol), K2CO3 (0.042 g, 0.30 mmol), 3-(chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole (0.143 g, 0.54 mmol) and CH3CN (5 mL) was stirred at 60° C. for 6 h. The mixture was diluted with EtOAc (25 mL) and washed with water (15 mL) and brine (15 mL). Drying (MgSO4), filtration, and concentration was followed by purification (SiO2, 0-30% EtOAc in hexanes) to afford the title compound (0.031 g, 22%) as a pale yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.29 (s, 1H), 8.23 (d, J=8.0 Hz, 1H), 7.86 (d, J=8.0 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H), 7.69-7.63 (m, 2H), 6.94 (s, 1H), 5.56 (s, 2H), 3.96 (q, 2H); MS m/z 517 (M−H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07572820B2 |
|---|
| Source dataset | uspto-grants-2009_08 |
|---|
| ORD ID | ord-adc16d7062cf4247b334b6a675658726 |
|---|
| Source note | uspto-grants-2009_08 |
|---|