2,2'-Bipyridine → 4-Bromo-1-cyclopropylpyridin-2(1H)-one

A flask charged with a stir bar, 4-bromo-1H-pyridin-2-one (1.80 g), cyclopropylboronic acid (2.00 g), Cu(O2CCH3)2 (2.00 g), 2,2′-bipyridine (1.70 g), Na2CO3 (2.47 g), and 1,2-dichloroethane (75 mL) was heated to 70° C. The mixture was stirred at this temperature in air overnight. Then, further portions of cyclopropylboronic acid (0.50 g) and Na2CO3 (0.55 g) were added and the mixture was stirred at reflux temperature for another 4 h. After cooling to ambient temperature, aqueous NH4Cl solution was added and the resultant mixture was extracted with dichloromethane. The combined organic extracts were dried (MgSO4) and the solvent was evaporated. The residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 50:50→35:65) to afford the title compound as an oil that crystallized on standing. Yield: 0.82 g (37% of theory); Mass spectrum (ESI+): m/z=214/216 (Br) [M+H]+.

1. additionA flask charged with a stir bar
2. stirringthe mixture was stirred
3. temperatureat reflux temperature for another 4 h
4. extractionthe resultant mixture was extracted with dichloromethane
5. dry with materialThe combined organic extracts were dried (MgSO4)
6. customthe solvent was evaporated
7. customThe residue was purified by chromatography on silica gel (cyclohexane/ethyl acetate 50:50→35:65)

ORD record

ord-8c3a072179f8406dafb2c4af0f4f3871

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629138B2