Reaction Steps
To a microwave vial containing 4-[(6-chloropyridin-3-yl)methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]quinoline-2-carboxamide (A) (100 mg, 0.25 morel), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazole (63 mg, 0.30 mmol), Pd2(dba)3 (2.3 mg, 2.5 μmol), and tricyclohexylphosphine (1.7 mg, 6.1 mop was added 0.84 mL of dioxane and 0.34 mL 1.7 M aqueous tribasic potassium phosphate. The reaction was heated to 140° C. in a microwave reactor for 1 h. The reaction mixture was extracted with ethyl acetate, dried over sodium sulfate, filtered, and concentrated. The resultant residue was subjected to purification via reverse phase HPLC to afford the title compound that gave a mass ion (ES+) of 442.2241 for M+H+. 1H NMR (400 MHz, CDCl3) δ 8.49 (d, J=2.0 Hz, 1H), 8.27 (d, J=7.3 Hz, 1H), 8.19 (s, 1H), 8.14 (d, J=8.6, 1H), 8.04 (d, J=8.4 Hz, 1H), 7.88 (d, J=9.7 Hz, 2H), 7.75 (t, J=7.1 Hz, 1H), 7.60 (t, J=7.7 Hz, 1H), 7.39 (dd, J=2.0, 8.1 Hz, 1H), 7.33 (d, J=8.2 Hz, 2H), 4.48 (s, 2H), 3.94 (s, 3H), 3.91-3.84 (m, 1H), 3.58 (m, 1H), 3.38 (br s, 1H) 2.16-2.13 (m, 2H), 1.92-1.79 (m, 2H), 1.52-1.31 (m, 4H).
