Cesium carbonate → HCID 86691825, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave vial, 3-bromo-4-methylbenzonitrile (250 mg, 1.28 mmol), Bispinnacoloto(diboron) (356 mg, 1.4 mmol), Potassium Acetate (560 mg, 5.74 mmol), and Bis(diphenylphosphino)ferrocene dicholoropalladium (180 mg, 0.25 mmol) was added under nitrogen and suspended in dioxane (2.5 ml). The mixture was refluxed at 90° C. overnight, and showed the intermediate boronic ester. The reaction was cooled to room temperature and to the reaction mixture was added 14-1 (191 mg, 0.76 mmol), cesium carbonate (830 mg, 2.6 mmol), bis(tri-t-butylphosphine)palladium(0) (65 mg, 0.13 mmol) and water (0.7 mL). The mixture was refluxed at 90° C. overnight, at the desired coupled product was observed by LC/MS. The mixture was diluted with methanol and purified using reverse phase chromatography (10-100%, 0.1% TFA in H2O/Acetonitrile); the desired fractions were collected and concentrated to produce 3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-4-methylbenzonitrile (15-1). HRMS (M+H)+: observed=335.1865, calculated=335.1866.

Provenance & Evidence