Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 3-(Chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole | HCID 2736622 | — |
| Reactant | HCID 86620683 | HCID 86620683 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86620685 | HCID 86620685 | 62% |
Reaction Steps
A mixture of 2,4-bis(trifluoromethyl)-1H-indole-5-carbonitrile (0.050 g, 0.18 mmol), Cs2CO3 (0.064 g, 0.20 mmoL), 3-(chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole (0.052 g, 0.20 mmoL) and CH3CN (4 mL) was stirred at 75° C. for 18 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 (0.056 g, 62%) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.34 (d, J=8.8 Hz, 1H), 8.29 (d, J=8.8 Hz, 1H) 8.23 (s, 1H), 8.09-8.06 (m, 2H), 7.83 (t, J=7.8 Hz, 1H), 7.48 (s, 1H), 6.03 (s, 2H); MS m/z 527 (M+Na).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07572820B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-e92951f074784bdeb7fe5d1b52d9416b |
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| Source note | uspto-grants-2009_08 |
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