Sodium hydride → HCID 25056868, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-hydroxy-1-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (100 mg, 0.308 mmol) in THF was added NaH (25 mg, 0.62 mmol) followed by 4-(trifluoromethyl)benzyl bromide (88 mg, 0.37 mmol). After heating at 65° C. overnight, the reaction mixture was cooled down, filtered through a thin layer of Celite, washed with CH2Cl2, and the filtrate was concentrated. Purification by flash column chromatography (silica gel, CH2Cl2/MeOH, 90:10) gave 1-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)-4-(4-(trifluoromethyl)benzyloxy)pyridine-2(1H)-one (20 mg, 13%) as a white solid. According to the procedure of Example 1, the HCl salt was made to give the title compound as a white solid: 1H NMR (500 MHz, DMSO-d6) δ 9.65 (s, 1H), 8.12 (m, 1H), 7.80-7.67 (m, 6H), 7.62 (d, J=7.5 Hz, 1H), 7.34 (m, 1H), 6.13 (dd, J=7.5, 2.5 Hz, 1H), 5.98 (d, J=2.5 Hz, 1H), 5.27 (s, 2H), 4.58-4.54 (m, 2H), 2.89 (m, 2H), 2.52-2.42 (m, 4H), 1.73-1.64 (m, 4H); ESI MS m/z 483 [M+H]+.

Provenance & Evidence