Dimethylformamide → HCID 178434286, compound

Participants

Reaction Conditions

Reaction Steps

To an Argon flushed flask of anhydrous THF (81 mL) cooled to −78° C. was added a 1.7M solution of tert-butyllithium in n-pentane (27 mL, 45.6 mmol). After stirring the solution at −78° C. for 15 minutes, a solution of 5-Bromo-3-methyl-1H-indazole (3 g, 14.2 mmol) in THF (42 mL) was added dropwise such that the temperature of the solution did not exceed −70° C. After stirring the solution at −78° C. for 30 minutes, anhydrous DMF (3.15 g, 43.09 mmol) was added dropwise. The reaction mixture was then stirred at −78° C. for 30 minutes, warmed to room temperature and stirred for 1.5 hours. The reaction mixture was cooled down to 0° C. and it was added carefully water (36 mL) and ethyl acetate. The ethyl acetate layer was washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo. The residue was purified by flash column chromatography on silica gel (heptane/EtOAc 6:4 v/v) to afford white solid (1.6 g, 70%).

Provenance & Evidence