Tert-butyl cis-(3-carbamoylcyclohexyl)carbamate → tert-butyl N-[(1R,3S)-3-[[4-(6,6-dimethyl-5,7-dihydropyrrolo[1,2-a]imidazol-3-yl)-5-fluoro-2-pyridinyl]carbamoyl]cyclohexyl]carbamate

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Tetrakis(triphenylphosphine)palladium(0) (43.5 mg, 0.04 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-6,6-dimethyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole (100 mg, 0.38 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (109 mg, 0.45 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (43.6 mg, 0.08 mmol) and Cesium carbonate (368 mg, 1.13 mmol) in 1,4-dioxane (5.98 ml). Degassed for 5 mins under nitrogen and the resulting suspension was stirred at 120 °C for 3 hours in the microwave reactor. The reaction mixture was partitioned between water (20ml) and DCM (40ml) and separated using a phase separation cartridge. The organics were absorbed onto silica and purified by flash silica chromatography, elution gradient 0 to 60% EtOAc in heptane. Pure fractions were evaporated to dryness to afford starting material (100mg).

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