Toluene → HCID 46833788, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4-hydroxy-piperidin-1-yl)-{4-[4-(4-iodobenzotriazol-1-yl)-pyrimidin-2-yl-amino]-cyclohexyl}-methanone (274 mg) and 3-thiopheneboronic acid (67 mg) was placed in a screw cap pressure flask, and Na2CO3 (2 M aq, 0.7 mL, degassed), toluene (5 mL, degassed) and EtOH (5 mL), added. To this was added Pd(PPh3)4 (20 mg), the flask sealed, and the mixture stirred overnight at 110° C. The reaction mixture was then cooled to RT, diluted in water, extracted in DCM, washed with water and brine, dried over Na2SO4, and the solvent stripped to yield a crude solid (0.25 g). The crude product was chromatographed on silica, and eluted with 0-70% Magic Base/DCM, titurated in Et2O, filtered, and evaporated to yield (4-hydroxy-piperidin-1-yl)-{4-[4-(4-thiophen-3-ylbenzotriazol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-methanone (Compound 6, 201 mg). mp=233-234° C.; M+H=504.

Provenance & Evidence