8-Hydroxyquinoline → 1-(2-methyl-4-(methylsulfonyl)phenyl)-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one

Participants

Reaction Steps

Example 178 was prepared according to the procedures described in Example 162 substituting 4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one for isopropyl 4-(methylsulfonyloxy)piperidine-1-carboxylate and 1-fluoro-2-methyl-4-(methylsulfonyl)benzene for 4-bromobenzonitrile in Step C except that the reaction was heated at 160° C. for 20 min. with copper(I) iodide, potassium carbonate and quinolin-8-ol in a Microwave as described in Step A of Example 1 instead of reflux at 120° C. in the presence of cesium carbonate for 10 h. 1H NMR (500 MHz, CDCl3) δ ppm 8.21 (br. s., 2H), 7.92 (s, 1H), 7.88 (d, J=7.70 Hz, 1H), 7.40 (d, J=7.70 Hz, 1H), 7.06 (d, J=6.05 Hz, 1H), 5.93-6.11 (m, 2H), 4.58 (br. s., 1H), 4.21 (br. s., 2H), 3.56-3.80 (m, 2H), 3.08 (s, 3H), 2.41 (t, J=7.42 Hz, 2H), 2.28 (s, 3H), 2.09 (d, J=9.90 Hz, 2H), 1.87 (br. s., 2H), 1.48-1.65 (m, 2H), 0.93 (t, J=7.42 Hz, 3 H). MS (ESI) 483 (M+H).

Provenance & Evidence