5-Chloro-1,3-benzodioxol-4-amine → N-[4-[(5-chloro-1,3-benzodioxol-4-yl)amino]-2-pyridinyl]acetamide

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Reaction carried out in two batches in 20 ml microwave tubes. 5-chlorobenzo[d][1,3]dioxol-4-amine (1 g, 5.83 mmol), N-(4-chloropyridin-2-yl)acetamide (0.994 g, 5.83 mmol), XANTPHOS (0.405 g, 0.70 mmol), PALLADIUM(II) ACETATE (0.065 g, 0.29 mmol) and CESIUM CARBONATE (3.80 g, 11.66 mmol) were suspended in 2x DMA (12mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. LC/MS showed completion. The reaction mixture was concentrated and diluted with EtOAc , and washed sequentially with water and saturated brine. The organic layer was dried over MgSO4, filtered and evaporated. The crude oil was triturated with EtOAc, Et2O and hexane to give a solid which was collected by filtration and dried under vacuum to give P1 N-(4-(5-chlorobenzo[d][1,3]dioxol-4-ylamino)pyridin-2-yl)acetamide (680mg, 38%)as a tan solid. NMR of this product showed product plus some DMA and aromatic impurities. The filtrate from the the above was concentrated and triturated again to give P2 N-(4-(5-chlorobenzo[d][1,3]dioxol-4-ylamino)pyridin-2-yl)acetamide (800mg, 45%) as a pale orange solid. NMR of this product showed it to be much cleaner than P1.

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