Water → HCID 86694712, compound

Participants

Reaction Steps

To a solution of 4-bromo-6-fluoro-1H-indazole (2.3 g, 10.7 mmol) in anhydrous DMF (36 mL) was added sodium hydride (60% dispersion in mineral oil, 0.51 g, 12.8 mmol, 1.2 eq.). After stirring at RT for 5 min, iodomethane (2.2 mL) was added, and the resulting mixture was stirred at RT overnight. The reaction mixture was poured into water (200 mL) and extracted with EtOAc (2×100 mL). The combined extracts were washed with water (200 mL) and brine (50 mL), dried (MgSO4), filtered, and evaporated in vacuo. The residue was purified by SiO2 chromatography eluting with hexane:EtOAc (3:1) to afford 4-bromo-6-fluoro-1-methyl-1H-indazole as a tan solid (1.42 g, 58%) and 4-bromo-6-fluoro-2-methyl-2H-indazole (0.29 g, 12%) as a tan solid. MS (ESI): m/z=229.1 [M+1]+.

Provenance & Evidence