Reacción #139

ord-43b38b44db094a5e90893913a2fe3478

Ecuación de reacción

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
Rendimiento 43.7%

Disolventes

Condiciones de reacción

Temperatura
150°CELSIUS

Procedimiento

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.

Fuente

750 AstraZeneca ELN dataset