Iodine → HCID 178506359, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-(trifluoromethoxy)-1H-indazole-3-carboxylic acid (0.2 g, 813 μmol), and sodium bicarbonate (225 mg, 104 μL, 2.68 mmol) in dichloroethane (2 mL) and water (2.00 mL) were added in one portion sodium iodide (317 mg, 2.11 mmol) and iodine (268 mg, 1.06 mmol) and the mixture heated at 100° C. (oil bath temperature) with vigorous stirring for 45 minutes. After cooling to 25° C. the mixture was diluted with dichloromethane, then washed with 10% Na2S2O3 and saturated NaHCO3. The organics were dried (MgSO4) and concentrated to an off-white solid which was dissolved in dichloromethane, cyclohexane added to promote solid formation, and allowed to stand. The solid was separated by filtration and dried to give 3-iodo-5-(trifluoromethoxy)-1H-indazole (178 mg, 543 μmol, 67%) as white needles. MS (M−H)−=326.8; 1H NMR (CDCl3) δ: 7.51 (d, J=9.1 Hz, 1H), 7.40 (s, 1H), 7.32-7.38 (m, 1H).

Provenance & Evidence