Ethyl Acetate → (Rac)-1-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-1-[2-(2-trimethylsilanyl-ethoxymethyl)-2h-indazol-5-yl]-ethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of (rac)-1-(6-chloro-imidazo[1,2-b]pyridazin-3-yl)-1-[2-(2-trimethylsilanyl-ethoxymethyl)-2H-indazol-5-yl]-ethanol (Stage 195.2, 400 mg, 0.901 mmol) in DME (4 mL) degassed with argon was added 1-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (281 mg, 1.351 mmol), followed by 2 M K2CO3 (1.216 mL) and PdCl2(PPh3)2 (19 mg). The RM was heated at 80° C. for 5 h. It was then taken into EtOAc and brine and extracted. Combined organic layers were dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (CombiFlash® Companion System®, with RediSep® silica gel column, EtOAc/MeOH=100:0->80:20) to afford the title compound (tR 4.56 min (conditions 3), MH+=490).

Provenance & Evidence