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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A mixture of N-(4-chloropyridin-2-yl)cyclopropanecarboxamide (1 g, 5.09 mmol), 6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-amine (0.878 g, 5.09 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.324 g, 0.56 mmol), diacetoxypalladium (0.090 g, 0.40 mmol), cesium carbonate (4.14 g, 12.71 mmol) and dioxane (18 mL) was degased, purged (x3) with argon and heated to reflux over a period of 4 hours in an oil bath (110°C). The reaction was complete. The reaction mixture was allowed to warm to room temperature diluted with water (25ml), a saturated solution of NH4Cl (35ml). Extraction with dichloromethane (x2), the organic was washed with a saturated aqueous solution of brine, dried over magnesium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 0 to 2% methanol in dichloromethane. The solvent was evaporated, the product was diluted in dichloromethane. The solution was filtered through PTFE filter 0.45µm, the filtrate was concentrated to dryness to afford N-(4-(6-chloro-[1,3]dioxolo[4,5-b]pyridin-7-ylamino)pyridin-2-yl)cyclopropanecarboxamide (1.200 g, 70.9 %) as a white crystalline solid.

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