Nitrogen → HCID 86710714, compound

Participants

Reaction Conditions

Reaction Steps

(4-Chloro-2-fluorophenyl)boronic acid (4.29 g, 24.6 mmol), Intermediate 1-1 (6.63 g, 23.4 mmol) and Na2CO3 (7.45 g, 70.3 mmol) were degassed for 10 minutes with N2, then PdCl2(dppf)CH2Cl2 (0.96 g, 1.17 mmol) was added. The reaction mixture was heated at 90° C. for 2 h. The reaction mixture was concentrated in vacuo then CH2Cl2 and 1 M HCl were added. The aqueous phase was washed with CH2Cl2, then basified to pH 14 with a 6 M NaOH solution. The aqueous phase was then extracted with CH2Cl2 (3×). The combined organic phases were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford 6-(4-chloro-2-fluorophenyl)-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine as a brown solid (8.40 g, 95%). [M+H]: 377.2; 1H NMR (400 MHz, MeOD) δ 7.87 (t, J=8.5 Hz, 1H), 7.76 (dd, J=9.5, 2.4 Hz, 1H), 7.32-7.40 (m, 2H), 7.17 (d, J=9.5 Hz, 1H), 5.13-5.36 (m, 1H), 1.69 (dd, J=12.5, 3.5 Hz, 2H), 1.57 (t, J=12.5 Hz, 2H), 1.38 (s, 6H), 1.23 (s, 6H).

Provenance & Evidence