(1-Bromoethyl)benzene → HCID 25057384, 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 (84 mg, 0.26 mmol) in DMF was added Ag2O (120 mg, 0.52 mmol) followed by 1-bromoethylbenzene (71 uL, 0.52 mmol). The reaction mixture was heated to 80° C. for 4 hours, cooled to room temperature and stirred at room temperature for overnight. The reaction mixture was 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 4-(1-phenylethoxy)-1-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (44 mg, 40%) as an oil. In accordance with the procedure of Example 1, the HCl salt was made to give the title compound as a white foam: 1H NMR (500 MHz, DMSO-d6) δ 9.82 (s, 1H), 8.15 (s, 1H), 7.75 (d, J=9.0 Hz, 1H), 7.69 (d, J=2.0 Hz, 1H), 7.49 (d, J=7.5 Hz, 1H), 7.38-7.31 (m, 5H), 7.26-7.24 (m, 1H), 6.04 (dd, J=7.5, 2.5 Hz, 1H), 5.69 (d, J=3.0 Hz, 1H), 5.51 (q, J=6.5 Hz, 1H), 4.77-4.75 (m, 2H), 3.66-3.63 (m, 2H), 3.46-3.45 (m, 2H), 3.00-2.99 (m, 2H), 1.93 (m, 2H), 1.78-1.75 (m, 2H), 1.51 (d, J=6.5 Hz, 3H); ESI MS m/z 429 [M+H]+.

Provenance & Evidence