Cesium carbonate → HCID 86663996, compound

Participants

Reaction Conditions

Reaction Steps

[7-(Ethylcarbamoyl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]trifluoromethanesulfonate (150 mg, 0.344 mmol), bis-(neopentyl glycolato)diboron (155 mg, 0.688 mmol) and potassium acetate (100 mg, 0.89 mmol) were weighed into a Kymax tube. DMF (4 mL) was added and the mixture degassed by bubbling N2 through for 15 min. Pd(dppf)Cl2 (28 mg, 0.0344 mmol) was added and the reaction sealed and heated to 80° C. for 3 h at the end of which time LCMS indicated clean boronate formation. The reaction was allowed to cool to ambient temperature then 1-(5-bromo-pyrimidin-2-yl)-4-ethyl-piperidine-4-carboxylic acid ethyl ester (169 mg, 0.516 mmol), cesium carbonate solution (185 μl, 0.688 mmol, 3.7M aq. soln.) and Pd(dppf)Cl2 (28 mg, 0.0344 mmol) were added and the reaction sealed and heated to 90° C. for 3 h at the end of which time LCMS indicated formation of the desired product. The reaction mixture was diluted with EtOAc, washed with water then brine and the organic layer dried (MgSO4), filtered and the solvent was removed in vacuo. The crude material obtained was purified by flash chromatography on silica gel using DCM:MeOH 96:4 as eluent. The product was obtained as a pale brown solid, 78 mg, 42% yield.

Provenance & Evidence