Phenylboronic Acid → 5-Benzyl-2-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-3-phenyl-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one

Participants

Reaction Steps

Reaction and post treatment were carried out in the same manner as in Example 1-(a) except for using 383 mg (0.552 mmol) of 5-benzyl-2-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)-3-iodo-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one obtained in Example 38-(c) in place of 2-bromo-1-(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one, using 84 mg (0.69 mmol) of phenylboronic acid in place of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane, and using 55 μl of tetrahydrofuran solution containing 100 mM palladium complex prepared previously from 231 mg (1.03 mmol) of palladium acetate and 846 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl in place of tetrakis(triphenylphosphine)palladium, whereby 330 mg of the title compound was obtained as a pale brownish foam. (Yield: 93%)

Provenance & Evidence