Reaktion #139

ord-43b38b44db094a5e90893913a2fe3478

Reaktionsgleichung

Nc1c(Cl)cnc2c1OCO2
Nc1c(Cl)cnc2c1OCO2
O=C(Nc1cc(Cl)ccn1)C1CC1
O=C(Nc1cc(Cl)ccn1)C1
O=C(Nc1cc(Nc2c(Cl)cnc3c2OCO3)ccn1)C1CC1
O=C(Nc1cc(Nc2c(Cl)cn
Ausbeute 43.7%

Lösungsmittel

Reaktionsbedingungen

Temperatur
150°CELSIUS

Vorschrift

N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (0.8 g, 4.07 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (0.702 g, 4.07 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.282 g, 0.49 mmol), diacetoxypalladium (0.046 g, 0.20 mmol) and cesium carbonate (2.65 g, 8.14 mmol) were suspended in 1,4-dioxane (15 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 100% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford N-(4-(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-ylamino)pyridin-2-yl)cyclopropanecarboxamide (0.592 g, 43.7 %) as a white solid.

Quelle

750 AstraZeneca ELN dataset