Dimethyl Sulfoxide → HCID 67451773, compound

Temperature

0 °C

To a 250 mL round bottom flask was added DMSO (60 mL) and 1-(3-fluoropyridin-2-yl)cyclobutanecarbonitrile (2.96 g, 16.8 mmol), and the mixture was stirred until homogenous. Potassium carbonate (7.0 g, 50.4 mmol) was then added and the reaction mixture was cooled to 0° C., followed by the addition of 35% hydrogen peroxide (6.5 mL). The reaction was stirred at 0° C. for 30 min and then warmed to rt. At this time, the reaction was diluted with water (50 mL) and ethyl acetate (100 mL). After transferring to a separatory funnel and shaking, the organic layer was separated from the aqueous layer and then washed with brine (3×50 mL). The organic layer was then dried over Na2SO4, filtered, and concentrated to give a crude solid that was purified by silica gel chromatography (10% EtOAC/hexanes) to afford 1.92 g of 1-(3-fluoropyridin-2-yl)cyclobutanecarboxamide as a white solid.

1. stirringThe reaction was stirred at 0° C. for 30 min
2. temperaturewarmed to rt
3. customAfter transferring to a separatory funnel
4. stirringshaking
5. customthe organic layer was separated from the aqueous layer
6. washwashed with brine (3×50 mL)
7. dry with materialThe organic layer was then dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customto give a crude solid that
11. customwas purified by silica gel chromatography (10% EtOAC/hexanes)

ORD record

ord-b56c5f2fec364b2284891b7933bea558

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133123B2