Dichloromethane → HCID 178468577, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 2-(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1-(trans-4-(tert-butyldimethylsilyloxy)cyclohexyl)-1H-benzo[d]imidazole-5-carboxylate (90.1 mg, 0.000121 mol) and 4-methoxypyridin-3-yl-3-boronic acid (22 mg, 0.00014 mol) were added to a 20 mL vial and dissolved in 1,4-dioxane (2 mL, 0.02 mol). To the reaction mixture was added 2 M sodium carbonate in water (0.3 mL) followed by the addition of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complexed with dichloromethane (1:1) (10 mg, 0.00001 mol). The reaction mixture was heated under nitrogen at 90° C. for 1 hour. The reaction mixture was diluted with ethyl acetate, washed with saturated sodium bicarbonate solution and brine. The organic phase was dried over sodium sulfate and concentrated. The residue was purified by combiflash chromatography using methanol/methylene chloride as eluent and a 40 g silica gel cartridge. A gradient was run from 0% methanol to 4% methanol over 20 minutes. Concentrating the product fractions under high vacuum gave 56.8 mg of the title compound as a foam.

Provenance & Evidence