4-Bromo-2,6-difluoroaniline → HCID 66997098, compound

Participants

Reaction Steps

Potassium acetate (0.344 g, 3.51 mmol) and bis(pinacolato)diboron (351 mg, 1.4 mmol) were added to a solution of 5-bromo-1,3-dimethyl-1H-indazole (240 mg, 1.06 mmol) in dioxane (10 ml) and mixture was degassed with nitrogen for 30 min. tetrakis(triphenylphosphine) palladium(0) was added and degassed for further 30 min. Reaction mixture was refluxed for 2 h. After completion of the reaction, work-up (AcOEt/H2O) followed by column afforded 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (85 mg) as a white solid. The title compound (26 mg) was prepared from 4-bromo-2,6-difluoroaniline (50 mg, 0.24 mmol) and 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (85 mg, 0.31 mmol) as a white solid. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 7.93 (s, 1H), 7.66 (dd, J 1.5, 8.8, 1H), 7.55 (d, J 8.8, 1H), 7.33 (dd, J 2, 8.2, 2H), 5.22 (s, 2H), 3.94 (s, 3H), 2.49 (s, 3H).

Provenance & Evidence