Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Chloro-6-(trifluoromethyl)pyridine | HCID 602334 | — |
| Reactant | HCID 71547981 | HCID 71547981 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 71548274 | HCID 71548274 | — |
Reaction Steps
To a solution of Example 57 (76.2 mg, 0.3 mmol) in dimethyl sulfoxide (0.3 mL) was added 2-chloro-6-(trifluoromethyl)pyridine (87 mg, 0.48 mmol) and sodium carbonate (64 mg, 0.6 mmol). The mixture was stirred at 100° C. for 4 days and then concentrated. The residue was purified by chromatography on silica gel (ethyl acetate/methanol=10:1) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.90 (m, 2H), 2.22-2.36 (m, 3H), 2.58 (m, 1H), 2.90-3.08 (m, 2H), 3.62 (m, 1H), 4.30 (m, 1H), 4.44 (m, 1H), 5.31 (m, 1H), 6.83 (d, 1H, J=7 Hz), 7.05 (d, 1H, J=7 Hz), 7.15 (d, 1H, J=7 Hz), 7.78 (m, 2H), 8.22 (s, 1H); MS (ESI) m/z 399 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08669255B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-a4d8a4f862974a9ab576aa2d4a3f9d44 |
|---|
| Source note | uspto-grants-2014_03 |
|---|