Cesium carbonate → 4-(4-(1-(5-cyclopropylpyrimidin-2-yl)piperidin-4-yloxy)-2-oxopyridin-1(2H)-yl)-3-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

Example 190 was prepared according to procedures described in Example 132 substituting tert-butyl 4-(1-(4-cyano-2-fluorophenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate (Example 176) for tert-butyl 4-(2-oxo-1-(pyridin-3-yl)-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate in Step C and substituting 2-chloro-5-cyclopropylpyrimidine (prepared according to the procedure described in Step A of Example 159) for 2-chloro-5-propylpyrimidine and substituting potassium carbonate for cesium carbonate in Step D except that reaction was stirred at 100° C. for 7 h. The crude solid was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2). 1H NMR (500 MHz, CDCl3) δ ppm 8.14 (s, 2H), 7.51-7.62 (m, 3H), 7.11 (d, J=7.70 Hz, 1H), 6.06 (dd, J=7.70, 2.75 Hz, 1H), 6.01 (d, J=2.75 Hz, 1 H), 4.52-4.62 (m, 1H), 4.15-4.26 (m, 2H), 3.58-3.68 (m, 2H), 1.96-2.14 (m, 2 H), 1.79-1.96 (m, 2H), 1.69-1.77 (m, 1H), 0.88-0.96 (m, 2H), 0.57-0.64 (m, 2 H). MS (ESI) 432 (M+H).

Provenance & Evidence