Dimethylformamide → 1-Benzyloxymethyl-3-formyl-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Participants

Reaction Steps

In 500 ml of an autoclave made of stainless were charged 45.3 g (86.8 mmol) of 1-benzyloxymethyl-3-iodo-5-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Reference example 33-(c), 390 mg (1.74 mmol) of palladium acetate, 1.92 g (3.47 mmol) of 1,1′-bis(diphenylphosphino)ferrocene, 30.2 ml (220 mmol) of triethylamine, 27.7 ml (170 mmol) of triethylsilane and 300 ml of N,N-dimethylformamide, and the mixture was stirred at 80° C. for 8 hours under carbon monoxide atmosphere of 15 atm. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with toluene. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=4:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 14.2 g of the title compound as a brownish solid. (Yield: 40%)

Provenance & Evidence