HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-[(3-Cyclohexyl-2-phenyl-pyrrolo[2,3-c]pyridin-6-yl)methyl]-3-[4-fluoro-2-(trifluoromethyl)phenyl]isoxazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 3-Cyclohexyl-2-phenyl-1H-pyrrolo[2,3-c]pyridine | HCID 25189721 | — |
| Reactant | 5-Chloromethyl-3-(4-fluoro-2-trifluoromethyl-phenyl)-isoxazole | HCID 46863996 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-[(3-Cyclohexyl-2-phenyl-pyrrolo[2,3-c]pyridin-6-yl)methyl]-3-[4-fluoro-2-(trifluoromethyl)phenyl]isoxazole | HCID 25189717 | 27% |
Reaction Steps
To 3-cyclohexyl-2-phenyl-1H-pyrrolo[2,3-c]pyridine (9 mg, 33 μmol) and 5-(chloromethyl)-3-(4-fluoro-2-(trifluoromethyl)phenyl)isoxazole (11 mg, 39 μmol) in DMF (326 μL) was added 10% aqueous NaOH (16 mL, 39 μmol). After stirring 12 h at room temperature, the reaction was neutralized with triethylamine and the crude purified by reverse phase HPLC to provide 4.5 mg (27%) of the title compound: 1H NMR (CD3OD, 300 MHz) δ 9.2 (s, 1H), 8.36 (s, 2H), 7.55-7.72 (m, 8H), 6.82 (s, 1H), 6.12 (s, 2H), 3.04 (m, 1H), 1.78-2.06 (m, 7H), 1.30-1.50 (m, 3H); LCMS found 520.3 (M++H, C30H26F4N3O requires 520.5).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09242983B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-644a52a61c934558a1ccb59ab58f021e |
| Source note | uspto-grants-2016_01 |