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

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To a stirred solution of N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (15 g, 76.28 mmol) in dioxane (200 mL) was added 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (13.16 g, 76.28 mmol), cesium carbonate (62.1 g, 190.71 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (4.86 g, 8.39 mmol) and diacetoxypalladium (1.370 g, 6.10 mmol). Mixture was degassed 3 times with N2 and heated at reflux (110°C) for 4h: OK. Reaction was cooled down, diluted with 200mL of CH2Cl2 and filtered. The filtrate was concentrated and the residue purified on silica, eluting with 2% of MeOH in CH2Cl2. Solvent were evaporated, diluted with a little CH2Cl2 until crystallisation occurs and diethyl ether was added. Solid was filtered, washed with diethyl ether and dried to afford N-(4-(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-ylamino)pyridin-2-yl)cyclopropanecarboxamide (15.00 g, 59.1 %) as a white powder. 1H NMR OK.

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