Cesium carbonate → 7-({2-[(Cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid

Participants

Reaction Steps

A mixture of N-(4-nitropyridin-2-yl)cyclopropanecarboxamide (2.75 g, 13.3 mmol), 7-hydroxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (2.55 g, 13.3 mmol) and Cs2CO3.(13.0 g, 39.8 mmol) in DMF (40 mL) was heated at 80° C. for 18 h. The reaction mixture was cooled to rt and concentrated. The residue was acidified to approximately pH 3 by the addition of 1N HCl. The precipitate was filtered and washed with water then hexane and dried under vacuum to provide 7-({2-[(cyclopropylcarbonyl)amino]pyridin-4-yl}oxy)-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (4.08 g, 87.2%) as a beige solid. LCMS: (FA) ES+ 353.2, ES− 351.3.

Provenance & Evidence