Water → HCID 19437750, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 810 mg (1.9 mmol) of 1-benzyl-3-bromo-7-(4-fluorobenzyloxy)-2-methylpyrrolo[2,3-d]pyridazine in 30 ml of anhydrous tetrahydrofuran is cooled to -70° C. under argon and treated with 1.65 ml (2.7 mmol) of a 15% strength solution of n-butyllithium in hexane. The mixture is subsequently stirred at -70° C. for a further 30 min. After addition of 215 μl (2.7 mmol) of anhydrous dimethylformamide, the temperature is kept at -70° C. for a further 30 min and subsequently slowly increased to 20° C. The solution is then treated with 100 ml of water and extracted with 3×50 ml of ethyl acetate. The organic extracts are washed with 50 ml of water, dried over magnesium sulfate and concentrated. The residue which remains is chromatographed on silica gel (eluent: ethyl acetate). After concentration of the fractions of Rf=0.4 and crystallization from diisopropyl ether, 150 mg (21%) of the title compound are isolated. M.p.: 136°-141° C.

Provenance & Evidence