Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Bromoacetamide | HCID 69632 | — |
| Reactant | HCID 86620728 | HCID 86620728 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86620730 | HCID 86620730 | 28.6% |
Reaction Steps
A mixture of 2-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile (Example 374A) (0.050 g, 0.17 mmol), Cs2CO3 (0.112 g, 0.34 mmol), 2-bromoacetamide (0.047 g, 0.34 mmol) and CH3CN (4 mL) was stirred at 70° C. for 2 h. The mixture was diluted with EtOAc (25 mL), washed with water (15 mL), brine (1 5 mL), dried over (MgSO4) and concentrated. The residue was stirred in EtOAc (5 mL) for 30 min. The resulting solid was filtered, rinsed with hexanes and dried to afford the title compound (0.017 g, 28%) as a tan solid: 1H NMR (400 MHz, DMSO-d6) δ 7.88 (d, J=8.6 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H), 7.72 (s, 1H), 7.38 (s, 1H), 6.78 (s, 1H), 5.01 (s, 2H), 4.07 (q, 2H); MS m/z 348 (M−H).
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-ea3777504bac4d329c06d61a3f95a7c8 |
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| Source note | uspto-grants-2009_08 |
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