Water → 6-(1H-Indol-4-yl)-4-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-indazole

Participants

Reaction Conditions

Reaction Steps

6-Bromo-4-(5-methyl-1,3,4-oxadiazol-2-yl)-1-[(4-methylphenyl)sulfonyl]-1H-indazole (70 mg, 0.162 mmol) was dissolved in 1,4-dioxane (1.2 ml) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (47.1 mg, 0.194 mmol, available from Frontier Scientific Europe), 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) (5.91 mg, 8.08 μmol), water (0.8 ml) and 2M aqueous sodium bicarbonate (0.242 ml, 0.485 mmol) were added. The reaction mixture was heated under microwave irradiation at 150° C. for 15 mins. The solution was loaded onto a silica cartridge (0.5 g) and eluted with methanol. The eluant was concentrated, the residue dissolved in methanol and absorbed onto Florisil. This was placed on top of a silica cartridge (10 g) and eluted with 25-50% ethyl acetate/cyclohexane. Appropriate fractions were evaporated to give the title compound as a yellow solid (27 mg).

Provenance & Evidence