1-Bromo-3-chloropropane → HCID 57625497, compound

Participants

Reaction Steps

To a solution of 5-bromo-1H-indazole (3.0 g, 15 mmol) in DMSO (15 mL) was added 1-bromo-3-chloropropane (2.0 mL, 20 mmol) and K2CO3 (6.33 g, 45.9 mmol). The reaction was stirred at room temperature for 72 h; then the reaction was diluted with methylene chloride (100 mL) and washed with a 5% LiCl solution (4×). The organics were washed with brine (50 mL), dried (Na2SO4), filtered, and concentrated. Purification by flash chromatography (40 g ISCO column, hexanes/EtOAc, 95:5 to 65:35) gave the title compound (2.14 g, 51%) as a white powder: 1H NMR (500 MHz, CDCl3) δ 7.95 (d, J=0.5, 1H), 7.87 (d, J=1.5 Hz, 1H), 7.48-7.45 (dd, J=8.9, 1.8 Hz, 1H), 7.38 (d, J=8.9 Hz, 1H), 4.54 (t, J=6.4 Hz, 2H) 3.47 (t, J=6.0 Hz, 2H) 2.42-2.37 (m, 2H); ESI MS m/z 273 [M+H]+.

Provenance & Evidence