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

Temperature

80 °C

A mixture 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 (0.25 g, 0.54 mmol) in DMF (10 mL) is added sodium chloro difluoro acetate (0.142 g, 1.09 mmol) and cesium carbonate (0.354 g, 1.09 mmol) at 0° C. and the reaction mixture is heated at 80° C. for 4 hours. The reaction mixture is diluted with ice cold water (50 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts are washed with saturated brine solution (20 mL), dried over sodium sulphate, filtered, and evaporated to dryness. The crude material is purified by silica gel (combiflash purifier 40 g redisep column) and is eluted with 45% EtOAc in hexane to give the title compound as a colorless semi solid (0.15 g, 55.5%). LCMS m/z 506 (M+H)+.

1. extractionextracted with EtOAc (2×20 mL)
2. washThe combined organic extracts are washed with saturated brine solution (20 mL)
3. dry with materialdried over sodium sulphate
4. filtrationfiltered
5. customevaporated to dryness
6. customThe crude material is purified by silica gel (combiflash purifier 40 g redisep column)
7. washis eluted with 45% EtOAc in hexane

ORD record

ord-e2087c02a76447b7823754d959f8018a

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09120793B2