Reaktion #622

ord-3648f11ef3b2438f8cb66069ce02004a

Reaktionsgleichung

CC1(C)Cc2ncc(-c3cc(Cl)ncc3F)n2C1
CC1(C)Cc2ncc(-c3cc(C
CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1
CC(C)(C)OC(=O)N[C@@H
CC1(C)Cc2ncc(-c3cc(NC(=O)[C@H]4CCC[C@@H](NC(=O)OC(C)(C)C)C4)ncc3F)n2C1
CC1(C)Cc2ncc(-c3cc(N
Ausbeute 80.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
120°CELSIUS

Vorschrift

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).

Quelle

750 AstraZeneca ELN dataset