Cesium carbonate → tert-Butyl {4-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]cyclohex-3-en-1-yl}carbamate

Participants

Reaction Conditions

Reaction Steps

To a microwave vial was added 5-chloro-1-(2,2-dimethylpropyl)-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (1-4) (410 mg, 1.616 mmol), Cs2CO3 (1.14 g, 3.50 mmol), tert-butyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl]carbamate (692 mg, 2.141 mmol), & bis(tri-t-butylphosphine)palladium(0) (183 mg, 0.358 mmol), followed by anhydrous 1,4-dioxane (2.5 mL) & water (0.5 mL). The reaction mixture was then heated to 100° C. for 10 minutes under microwave irradiation. The reaction was then cooled to room temperature, diluted with MeOH & NMP, filtered & resulting residue was purified by reverse-phase chromatography (10-100% CH3CN:0.1% TFA in H2O) to yield tert-Butyl {4-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]cyclohex-3-en-1-yl}carbamate (17-1) as a yellow solid/foam. HRMS m/z (M+H): calculated=415.2704; observed=415.2705

Provenance & Evidence