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A mixture of (E)-4-(4-((dimethylamino)methyl)benzylideneamino)-6-fluoroisobenzofuran-1(3H)-one (500 mg, 1.6 mmol) and 4-fluorobenzaldehyde (218 mg, 1.76 mmol) in ethyl propionate (10 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (110 mg, 4.8 mmol) in ethanol (5 mL)) was added dropwise. After the addition the mixture was stirred at room temperature for 3 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water and then extracted with ethyl acetate (100 mL×4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product, which was purified by chromatography (silica gel, petroleum ether/ethyl acetate=1:1) to give the title compound (100 mg, yield 13%). LC-MS (ESI) m/z: 465 (M+1)+.

1. additionAfter the addition the mixture
2. customThe mixture was quenched with water (10 mL) and solvent
3. customwas removed in vacuum
4. dissolutionThe residue was dissolved in water
5. extractionextracted with ethyl acetate (100 mL×4)
6. washThe combined organic layers were washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated
9. customto give crude product, which
10. customwas purified by chromatography (silica gel, petroleum ether/ethyl acetate=1:1)