Dimethyl Sulfoxide → HCID 67451773, compound

Temperature

0 °C

To a 250 mL round bottom flask containing DMSO (60 mL) was added 1-(3-fluoropyridin-2-yl)cyclobutanecarbonitrile (2.96 g, 16.8 mmol, 1.0 equiv) and the mixture was stirred until homogenous. Potassium carbonate (7.0 g, 50.4 mmol, 3.0 equiv) 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 room temperature. 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 (59%) 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 room temperature
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-00462ed948ef44269baae3826002247a

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018223B2