HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → (S)-3-(4-{2-[4-(3-Hydroxy-3-methyl-butoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-yl methoxy}-phenyl)-hex-4-ynoic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Bromo-2-methylbutan-2-ol | HCID 10607172 | — |
| Reactant | (S)-3-{4-[2-(4-Hydroxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester | HCID 136992561 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (S)-3-(4-{2-[4-(3-Hydroxy-3-methyl-butoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-yl methoxy}-phenyl)-hex-4-ynoic acid ethyl ester | HCID 118129976 | 100% |
Reaction Steps
To a stirred solution of (S)-3-{4-[2-(4-hydroxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester (0.2 g, 0.43 mmol) in acetonitrile (20 mL) is added 4-bromo-2-methyl-butan-2-ol (0.14 g, 0.87 mmol) and cesium carbonate (0.41 g, 1.2 mmol) and the reaction mixture is stirred at room temperature for 2 hours. The reaction mixture is filtered and evaporated to dryness. The crude material is purified by silica gel chromatography (combiflash purifier 24 g redisep column) and is eluted with 15-20% EtOAc in hexane to give the title compound (0.23 g, 100%). LCMS m/z 542 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09120793B2 |
| Source dataset | uspto-grants-2015_09 |
| ORD ID | ord-126887e2e6394d5e837a097c177a4ffc |
| Source note | uspto-grants-2015_09 |