Cesium carbonate → Benzyl {3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-6,6-dimethylcyclohex-2-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) (313 mg, 1.234 mmol), Cs2CO3 (804 mg, 2.467 mmol), benzyl [6,6-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-2-en-1-yl]carbamate (668 mg, 1.734 mmol), & bis(tri-t-butylphosphine)palladium(0) (129 mg, 0.252 mmol), followed by anhydrous 1,4-dioxane (2.5 mL) & water (0.5 mL). The reaction mixture was then heated to 100° C. for 2×10 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 benzyl {3-[1-(2,2-dimethylpropyl)-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-yl]-6,6-dimethylcyclohex-2-en-1-yl}carbamate (16-1) as a white solid/foam. HRMS m/z (M+H): calculated=477.2860; observed=477.2865.

Provenance & Evidence