4-(4-Chloro-2-fluorobenzyloxy)pyridin-2(1H)-one → HCID 66603475, compound

Participants

Reaction Steps

9-Bromo-7-methyl-2,3,5,6,7,11c-hexahydro-1H-pyrido[3′,2′:4,5]pyrrolo[2,3-g]indolizine (156 mg, 0.511 mmol) and 4-(4-chloro-2-fluorobenzyloxy)pyridin-2(1H)-one (129 mg, 0.511 mmol) were reacted following the procedure for Example 2 (step b) to provide the title compound (58 mg, 22%) as a yellow solid: mp 150-160° C.; 1H NMR (500 MHz, DMSO-d6) δ 11.30 (s, 1H), 8.11-8.09 (d, J=8.2 Hz, 1H), 7.83-7.81 (d, J=7.7 Hz, 1H), 7.65-7.62 (t, J=8.2 Hz, 1H), 7.55-7.53 (d, J=8.5 Hz, 1H), 7.40-7.36 (m, 2H), 6.17-6.15 (dd, J=7.7, 2.5 Hz, 1H), 6.07-6.05 (d, J=2.5 Hz, 1H), 5.20 (s, 2H), 5.02-5.00 (m, 1H), 3.72 (s, 3H), 3.63-3.34 (m, 3H), 3.32-3.28 (m, 1H), 3.25-3.14 (m, 2H), 2.64-2.55 (m, 1H), 2.14-2.10 (m, 2H), 2.09-1.95 (m, 1H); ESI MS m/z 479 [M+H]+; HPLC (Method B) 95.5% (AUC), tR=14.1 min.

Provenance & Evidence