1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 59362938, compound

Participants

Reaction Conditions

Reaction Steps

A glass tube was charged with 1-[4-(2-chloro-6,7-dihydro-5H-cyclopentapyrimidin-4-ylamino)-phenyl]-cyclobutanecarboxylic acid methyl ester (0.5 g, 1.4 mmol), 1-methyl-1H-pyrazole-5-boronic acid pinacol ester (0.42 g, 2 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) (0.081 g, 0.1 mmol) and alternatively purged and backfilled with nitrogen. After addition of anhydrous toluene (10 mL), EtOH (5 mL), and sodium carbonate (2M, 2 mL) the glass tube was sealed and heated at 100° C. under stirring until the reaction was complete as evidenced by the disappearance of starting chloro compound (TLC). The resulting mixture was cooled to a temperature in the range of 15° C. to 40° C., diluted with ethyl acetate (20 mL), filtered through Celite, washed with ethyl acetate, and the combined filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel to afford the title compound as a light yellow solid (0.27 g, 48%).

Provenance & Evidence