Dichloromethane → (1-cyclohexyl-2-(5-(4-methoxypyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1H-benzo[d]imidazol-5-yl)methanol

Participants

Reaction Steps

In a small microwave tube was added (2-(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1-cyclohexyl-1H-benzo[d]imidazol-5-yl)methanol (164 mg, 0.000287 mol), 4-methoxypyridin-3-ylboronic acid (79.1 mg, 0.000517 mol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II),complex with dichloromethane (1:1) (47 mg, 0.000057 mol). To this mixture was added 1,4-dioxane (4.3 mL, 0.055 mol) and the resultant mixture was stirred under an argon atmosphere. To this mixtrure was then added 2 M sodium carbonate in water (700 uL) and the reaction mixture was microwaved for 21 minutes at 120° C. The reaction mixture filtered through a syringe filter cartridge and the cartridge washed 3 times with methanol. The residue after concentration was purified by flash chromatography using a 40 g silica gel cartridge and 10-60% ethyl acetate/hexane gradient. The product fractions were concentrated to give the title compound (29 mg).

Provenance & Evidence