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A mixture of 200 mg (0.88 mmol) of 4-chlorobenzo[4,5]furo[3,2-b]pyridine-3-carbonitrile and 0.11 mL (0.97 mmol) of 4-chloro-2-fluoroaniline in 6 mL of 2-ethoxyethanol is heated at reflux temperature for 4 days. A catalytic amount of pyridine hydrochloride is added and the reaction mixture is heated at reflux temperature overnight then cooled to room temperature. The reaction mixture is partitioned between ethyl acetate and water. The organic layer is dried over sodium sulfate, filtered through a pad of diatomaceous earth and concentrated in vacuo to provide 120 mg (40%) of a beige solid, mp 259–261° C.

1. temperatureis heated
2. temperatureat reflux temperature for 4 days
3. temperaturethe reaction mixture is heated
4. temperatureat reflux temperature overnight
5. customThe reaction mixture is partitioned between ethyl acetate and water
6. dry with materialThe organic layer is dried over sodium sulfate
7. filtrationfiltered through a pad of diatomaceous earth
8. concentrationconcentrated in vacuo