HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 2-{8-[4-fluoro-3-(trifluoromethyl)phenoxy]-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}propan-2-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | ethyl 8-[4-fluoro-3-(trifluoromethyl)phenoxy]-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate | HCID 66606976 | — |
| Reactant | HCID 178418573 | HCID 178418573 | — |
| Product | 2-{8-[4-fluoro-3-(trifluoromethyl)phenoxy]-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}propan-2-ol | HCID 66603970 | — |
Reaction Steps
To a mixture of ethyl 8-[4-fluoro-3-(trifluoromethyl)phenoxy]-3-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylate (103.1 mg) in THF (1.8 mL) was added methylmagnesium bromide (1M THF solution, 920 μL) at room temperature, and the mixture was stirred at room temperature for 1 hr. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (31.5 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822699B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-02ea80da21e448a1b149dbaf01e53cde |
| Source note | uspto-grants-2014_09 |