Cesium carbonate → 1-(2,2-Dimethylpropyl)-5-[2-(4-methoxyphenyl)-6-methyl-2-azabicyclo-[2.2.2]oct-5-en-5-yl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Participants

Reaction Conditions

Reaction Steps

2-(4-Methoxyphenyl)-6-methyl-2-azabicyclo[2.2.2]oct-5-en-5-yl trifluoromethanesulfonate (7-2, 429 mg, 1.14 mmol, 1.0 equiv), bis(pinocolato)diboron (317 mg, 1.25 mmol, 1.1 equiv), potassium acetate (334 mg, 3.41 mmol, 3.0 equiv) and PdCl2(dppf) (58.2 mg, 0.079 mmol, 0.07 equiv) were added to anhydrous 1,4-dioxane (1.4 mL) and heated to 60° C. After 18 h, the reaction contents were cooled to RT, followed by the subsequent addition of water (289 μL), 5-chloro-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]-pyridin-2-one (1-4, 288 mg, 1.14 mmol, 1.0 equiv), Cs2CO3 (744 mg, 2.28 mmol, 2.01 equiv) and Bis(tri-tert-butylphosphine)palladium(0) (75 mg, 0.148 mmol, 0.13 equiv). The resulting mixture was heated to 60° C. for 4.5 h. Following this duration, LCMS showed consumption of starting material. The contents were then cooled to room temperature, diluted with ethyl acetate (10 mL), filtered through Celite and rinsed with ethyl acetate (3×7 mL) and water (1×3 mL).

Provenance & Evidence