Sodium Carbonate → HCID 57940589, compound

Participants

Reaction Steps

To a flame dried flask equipped with stir bar was added crude 1-[(4-nitrophenyl)sulfonyl]-5-phenyl-1,2,5,6-tetrahydropyridin-3-yl trifluoromethanesulfonate (1-5) (376 mg, 0.76 mmol), 2,5-difluorophenyl boronic acid (240 mg, 1.5 mmol), and Na2CO3 (243 mg, 2.3 mmol). The solids were dissolved in 5 mL 4:1 DME/H2O and degassed with N2. Pd(PPh3)4 (9 mg, 0.008 mmol) was added and the reaction was sealed under N2 and heated to 90 C for 2 h. Upon completion, the reaction was diluted with CH2Cl2, washed with 5% NaHCO3 and dried over MgSO4. Following filtration, the organic layer was concentrated and purified via ISCO (SiO2, 0-50% EtOAc/hexanes gradient) to provide 5-(2,5-difluorophenyl)-1-[(4-nitrophenyl)sulfonyl]-3-phenyl-1,2,3,6-tetrahydropyridine (1-6). 1H NMR (300 MHz, CDCl3) δ 8.35 (d, J=8.8 Hz, 2H), 7.94 (d, J=8.8 Hz, 2H), 7.34 (in, 5H), 7.20 (m, 1H), 7.02 (m, 2H), 6.09 (s, 1H), 4.27 (m, 1H), 3.94 (m, 1H), 3.82 (m, 2H), 2.86 (dd, J=12.0, 8.0 Hz, 1H); MS 457.3 found 457.5 (M+H+) required.

Provenance & Evidence