N-(4-chloropyridin-2-yl)cyclopropanecarboxamide → N-[4-[(6-Chloro-[1,3]dioxolo[4,5-B]pyridin-7-Yl)amino]-2-Pyridyl]cyclopropanecarboxamide

Temperature

150 °C

N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (4 g, 20.34 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (3.51 g, 20.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (1.412 g, 2.44 mmol), diacetoxypalladium (0.228 g, 1.02 mmol) and cesium carbonate (13.26 g, 40.68 mmol) were suspended in 1,4-dioxane (75 mL) and sealed into 5 microwave tubes. 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 (250 mL) and washed with water (250 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 and orange gum. The gum was dissolved in a little ether, then isohexane was added to precipitate N-(4-(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-ylamino)pyridin-2-yl)cyclopropanecarboxamide (2.180 g, 32.2 %) as a white solid.

ORD record

ord-e3d1bf887b8743b5ab0b5887f32d7a64

Source dataset

750 AstraZeneca ELN dataset

Original link

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