Toluene → HCID 46833493, compound

Participants

Reaction Steps

A mixture of (4-hydroxy-piperidin-1-yl)-{4-[4-(4-iodobenzotriazol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-methanone (0.25 g), 4-methyl-3-thiopheneboronic acid (0.068 g) and Na2CO3 (2 M, 0.7 mL, degassed) was stirred at RT under N2 for 15 min. To this was added Pd(PPh3)4 (0.016 g) with toluene (8 mL, degassed) and EtOH (0.5 mL), and the mixture stirred overnight at 110° C. The reaction mixture was then diluted in water, extracted in DCM, washed with water and brine, dried over Na2SO4, and the solvent stripped to yield a solid. The solid was flash-chromatographed on silica, eluting with DCM: 1% NH4OH-MeOH (1000:50) to provide (4-hydroxy-piperidin-1-yl)-(4-{-4-[4-(4-methylthiophen-3-yl)-benzotriazol-1-yl]-pyrimidin-2-yl-amino}-cyclohexyl)-methanone (Compound 1, 0.114 g, 40%) as an off-white solid. Mp=246-247° C.; M+H=518.

Provenance & Evidence