2,2'-Bipyridine → 5-Bromo-1-cyclopropylpyridin-2(1H)-one

Temperature

70 °C

A mixture of 5-bromo-2-hydroxypyridine (0.8300 g, 4.77 mmol, 1.0 equiv), Cu(OAc)2 (0.902 g, 4.96 mmol, 1.04 equiv), bipyridine (0.785 g, 5.03 mmol, 1.05 equiv), cyclopropylboronic acid (0.846 g, 9.85 mmol, 2.06 equiv) and Na2CO3 (1.110 g, 10.47 mmol, 2.20 equiv) in dichloroethane (30 mL) was stirred at 70° C. for 22 h under air. The reaction mixture was quenched with satd aq NH4Cl, diluted with CH2Cl2, dried over Na2SO4. After the solvent was removed under reduced pressure, the residue was purified by chromatography on silica gel eluted with hexanes/EtOAc to afford 0.585 g (58%) of 5-bromo-1-cyclopropylpyridin-2(1H)-one. LC-MS Method 1 tR=1.05 min, m/z 214, 216 (MH+); 1H NMR (400 MHz, CDCl3) δ 7.41 (d, J=2.7 Hz, 1H), 7.31 (dd, J=9.7, 2.9 Hz, 1H), 6.47 (d, J=9.9 Hz, 1H), 3.33-3.27 (m, 1H), 1.17-1.12 (m, 2H), 0.89-0.84 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 162.58, 142.29, 137.00, 121.77, 97.92, 32.83, 6.93.

1. customThe reaction mixture was quenched with satd aq NH4Cl
2. additiondiluted with CH2Cl2
3. dry with materialdried over Na2SO4
4. customAfter the solvent was removed under reduced pressure
5. customthe residue was purified by chromatography on silica gel
6. washeluted with hexanes/EtOAc

ORD record

ord-74f98b5bf2724947b79103ce81f14d3e

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08754076B2