Cesium carbonate → 6-(2-(Cyclopropanecarboxamido)pyridin-4-yloxy)quinoline-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

N-(4-Nitropyridin-2-yl)cyclopropanecarboxamide (Int-23, 150 mg, 0.722 mmol), 6-hydroxyquinoline-3-carboxylic acid (Int-15, 150 mg, 0.794 mmol), and cesium carbonate (706 mg, 2.17 mmol) were weighed into a 2-5 mL microwave vial. N,N-dimethylformamide (3.5 mL) was added and the vial was capped. The reaction mixture was heated in the microwave for 3 h at 150° C. The vial was allowed to cool to room temperature and the cap was removed. The reaction mixture was diluted with water (5 mL) and stirred for a few minutes. The resulting clear solution was acidified by addition of 1N HCl and extracted three times with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. A solid precipitated in the extracts, was isolated by filtration and found to be the product. Solid product was combined with product isolated by extraction (0.245 g, 97%). LC-MS: (FA) ES+ 350; 1H NMR (400 MHz, d6-DMSO) δ ppm 13.67-13.47 (m, 1H), 10.92 (s, 1H), 9.30 (d, J=2.1 Hz, 1H), 8.98 (d, J=2.0 Hz, 1H), 8.25 (d, J=5.7 Hz, 1H), 8.21-8.17 (m, 1H), 8.01-7.99 (m, 1H), 7.75 (dd, J=9.1, 2.7 Hz, 1H), 7.70 (d, J=2.3 Hz, 1H), 6.81 (dd, J=5.7, 2.4 Hz, 1H), 1.95 (tt, J=7.6, 7.6, 4.9, 4.9 Hz, 1H), 0.81-0.67 (m, 4H).

Provenance & Evidence