Toluene → (4-Hydroxy-piperidin-1-yl)-{4-[4-(4-thiophen-3-yl-indol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-methanone

Participants

Reaction Conditions

Reaction Steps

A mixture of {4-[4-(4-bromo-indol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-(4-hydroxy-piperidin-1-yl)-methanone (0.51 g), 3-thiophene-boronic acid (0.16 g) and Na2CO3 (2 M aq, 1.53 mL, degassed), toluene (12 mL, degassed) and EtOH (12 mL) was added to a screw cap pressure flask. To this was added Pd(PPh3)4 (0.035 g), the flask sealed, and the mixture stirred overnight at 110° C. The reaction mixture was then diluted with water, extracted in DCM, washed with water and brine, dried over Na2SO4, and the solvent stripped to yield a yellow 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-thiophen-3-yl-indol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-methanone (Compound 18, 0.32 g, 63%) as a light yellow powder. Mp=171-172° C., M+H=502.

Provenance & Evidence