Dichloromethane → 2-Chloro-4-(4-(oxetan-2-yl)pyridin-3-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To the solution of 2-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (569 mg, 2.16 mmol), 3-bromo-4-(oxetan-2-yl)pyridine (462 mg, 2.16 mmol) and PdCl2(dppf).CH2Cl2 adduct (176 mg, 0.216 mmol) in DMF (10 mL) was added a solution of Na2CO3. (2 M, 2.70 ml, 5.40 mmol) under Nitrogen atmosphere. The mixture was stirred and heated at 100° C. for 4 hrs. Reaction mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed with water and brine. The aqueous layer was extracted with EtOAc. The combined organic phases were dried with Na2SO4, filtered and concentrated in vacuo. Purification by ISCO 12 g (0-40% EtOAc/Heptane) to give 2-chloro-4-(4-(oxetan-2-yl)pyridin-3-yl)benzonitrile (54 mg, 9%) as colorless solid; ESI-MS m/z: 271 [M+H]+, Retention time 1.42 min. 1H-NMR (MeOD, 400 MHz) δ 2.58-2.67 (m, 1H), 2.82-2.90 (m, 1H), 4.61-4.67 (m, 1H), 4.77-4.83 (m, 1H), 5.88 (t, J=7.6 Hz, 1H), 7.46 (dd, J=8.0, 1.2 Hz, 1H), 7.67 (d, J=1.2 Hz, 1H), 7.94 (d, J=8.0 Hz, 1H), 7.96 (d, J=4.8 Hz, 1H), 8.47 (s, 1H), 8.74 (d, J=4.8 Hz, 1H);

Provenance & Evidence