Reaktion #694

ord-c9fc8ca9766b49dfbbd86d67f996e21e

Reaktionsgleichung

Fc1cnc(Cl)cc1-c1cnn2c1CCCC2
Fc1cnc(Cl)cc1-c1cnn2
CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(N)=O)C1
CC(C)(C)OC(=O)N[C@@H
CC(C)(C)OC(=O)N[C@@H]1CCC[C@H](C(=O)Nc2cc(-c3cnn4c3CCCC4)c(F)cn2)C1
CC(C)(C)OC(=O)N[C@@H
Ausbeute 37.4%

Lösungsmittel

Reaktionsbedingungen

Temperatur
120°CELSIUS

Vorschrift

Tetrakis(triphenylphosphine)palladium(0) (0.092 g, 0.08 mmol) was added to 3-(2-chloro-5-fluoropyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine (0.200 g, 0.79 mmol), tert-butyl ((1R,3S)-3-carbamoylcyclohexyl)carbamate (0.231 g, 0.95 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.092 g, 0.16 mmol) and Cesium carbonate (0.777 g, 2.38 mmol) in 1,4-dioxane (5.98 ml). Degassed for 5 mins under nitrogen and the resulting suspension was stirred at 120 °C for 2 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. Still impure but telescoped through to next stage without further purification. (136mg).

Quelle

750 AstraZeneca ELN dataset