Cesium carbonate → (S)-3-(4-{2-[4-(2-Methoxy-ethoxy)-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy}-phenyl)-hex-4-ynoic acid ethyl ester

To a stirred solution (S)-3-{4-[2-(4-hydroxy-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-6-ylmethoxy]-phenyl}-hex-4-ynoic acid ethyl ester (0.250 g, 0.585 mmol) and 1-bromo-2-methoxy-ethane (0.22 mL, 2.34 mmol) in acetonitrile (10 mL) is added cesium carbonate (0.381 g, 1.17 mmol) at room temperature and the reaction mixture is stirred at room temperature overnight. The reaction mixture is filtered through diatomaceous earth and washed with EtOAc (20 mL), and the filtrate is concentrated to dryness. The residue is dissolved in EtOAc (30 mL), washed with water (2×30 mL), brine solution (30 mL), dried over sodium sulphate, and evaporated under reduced pressure. The crude compound is purified by silica gel (combiflash purifier) and is eluted with 17-19% EtOAc in hexane to give the title compound as a white semi solid (0.190 g, 64%). LCMS m/z 514 (M+H)+.

1. filtrationThe reaction mixture is filtered through diatomaceous earth
2. washwashed with EtOAc (20 mL)
3. concentrationthe filtrate is concentrated to dryness
4. dissolutionThe residue is dissolved in EtOAc (30 mL)
5. washwashed with water (2×30 mL), brine solution (30 mL)
6. dry with materialdried over sodium sulphate
7. customevaporated under reduced pressure
8. customThe crude compound is purified by silica gel (combiflash purifier)
9. washis eluted with 17-19% EtOAc in hexane

ORD record

ord-2171cea8d0b44ed3861e82101131b90b

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09120793B2