5-Bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazole → 4-((5-Chloropyridin-2-yl)methoxy)-1-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one hydrochloride

Participants

Reaction Steps

5-Bromo-1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazole (200 mg, 0.68 mmol) and 4-((5-chloropyridin-2-yl)methoxy)pyridin-2(1H)-one (160 mg, 0.68 mmol) were reacted according to the procedure in Example 63 (step c) to provide the title compound (119 mg, 36%) as a brown solid: mp 95-101° C. deliquesced; 1H NMR (500 MHz, CD3OD) δ 8.63 (s, 1H), 8.23 (s, 1H), 8.00-7.98 (dd, J=8.3, 2.1 Hz, 1H), 7.82 (d, J=19 Hz, 1H), 7.79 (d, J=8.9 Hz, 1H), 7.66-7.64 (2 overlapping d, J=8.5, 7.6 Hz, 2H), 7.47-7.44 (dd, J=8.9, 1.8 Hz, 1H), 6.41-6.39 (dd, J=7.5, 2.8 Hz, 1H), 6.16 (d, J=2.6 Hz, 1H), 5.30 (s, 2H), 4.87 (t, J=5.9 Hz, 2H), 3.86 (t, J=5.9 Hz, 2H), 3.72 (m, 2H), 3.19-3.13 (m, 2H), 2.18-2.15 (m, 2H), 2.03-1.99 (m, 2H); ESI MS m/z 450 [M+H]+; HPLC (Method D) 97.4% (AUC), tR=11.9 min.

Provenance & Evidence