Cesium carbonate → 7-chloro-2-(difluoromethyl)-2H-pyrazolo[3,4-c]pyridine

Temperatur

95 °C

A mixture of 7-chloro-1H-pyrazolo[3,4-c]pyridine (4.99 g, 32.5 mmol), sodium chlorodifluoroacetate (14.86 g, 97 mmol), and cesium carbonate (40.2 g, 123 mmol) in DMF (81 ml) was heated at 95° C. for 4 h. The reaction was allowed to cool to rt and the solids were filtered. The filtrate was diluted with water and extracted with EtOAc. The organic extract was washed with water, satd NaCl, dried over MgSO4, filtered and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (100 g), eluting with a gradient of 5% to 60% EtOAc in hexane, to provide a white solid (1.4117 g, 6.93 mmol, 21.34% yield). MS m/z=203.9 [M+H]+. Calculated for C7H4ClF2N3: 203.

1. temperatureto cool to rt
2. filtrationthe solids were filtered
3. additionThe filtrate was diluted with water
4. extractionextracted with EtOAc
5. extractionThe organic extract
6. washwas washed with water
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customchromatographed through a Biotage SNAP HP-silica gel column (100 g)
11. washeluting with a gradient of 5% to 60% EtOAc in hexane

ORD-Eintrag

ord-4ca554dc963e4db29d430d247b0bde85

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09296734B2