Cesium carbonate → 3-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid methyl ester

温度

90 °C

To a solution of 3-chloro-pyridine-4-carboxylic acid methyl ester (0.28 g, 1.65 mmol) in DMF (10 ml) are added cesium carbonate (2.68 g, 8.25 mmol) and 3,3-difluoro-3-(4-fluorophenyl)-propane-1-thiol (synthesized according to the methods described in sections a) and b) of example 3) (0.34 g, 1.65 mmol) in a sealed tube. The reaction mixture is stirred at 90° C. for 1 h. After completion of the reaction, the mixture is diluted with water (15 ml) and extracted with EtOAc (3×20 ml). The organic layer is washed with water (20 ml), brine (20 ml), dried over anhydrous sodium sulfate and evaporated to get the crude product, which is purified by column chromatography (silica gel, 10% acetone/hexane) to yield 3-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-pyridine-4-carboxylic acid methyl ester (0.19 g, 0.56 mmol, 34%).

1. customsynthesized
2. customAfter completion of the reaction
3. extractionextracted with EtOAc (3×20 ml)
4. washThe organic layer is washed with water (20 ml), brine (20 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. customevaporated
7. customto get the crude product, which
8. customis purified by column chromatography (silica gel, 10% acetone/hexane)

ORDレコード

ord-b879061a85c447d7833a3fb4f337e5e4

出典データセット

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09284286B2