反应详情

5-bromo-6-chloro-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from Example 66a (375 mg, 1 mmol), phenylboronic acid (146 mg, 1.2 mmol) and Pd(0) (35 mg) were mixed together in toluene (2 mL), and the mixture was heated at reflux for 16 hours. NaHCO3 solution (2%, mL) was added, and the mixture was extracted with CHCl3. The CHCl3 was removed under reduced pressure, and the residue was chromatographed on a silica gel column, eluting with EtOAc/hexane 1:1 to afford the title compound (280 mg). MS (CI/NH3) m/z 375 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ1.40 (s, 9H), 2.33-2.43 (m, 2H), 3.29 (t, J=7.5 Hz, 2H), 4.15 (dd, J=2.5, 7.5 Hz, 1H), 4.32-4.42 (m, 1H), 4.48-4.57 (m, 1H), 7.25-7.29 (m, 4H), 7.28 (d, J=2 Hz, 1H), 7.42-7.48 (m, 5H), 8.12 (d, J=3 Hz, 1H).

1. temperaturethe mixture was heated
2. temperatureat reflux for 16 hours
3. extractionthe mixture was extracted with CHCl3
4. customThe CHCl3 was removed under reduced pressure
5. customthe residue was chromatographed on a silica gel column
6. washeluting with EtOAc/hexane 1:1