Bis(trimethylsilyl)carbodiimide → 7-Fluoro-6-(2-fluoro-pyridin-3-yl)-2-phenylchroman-4-ylidene-cyanamide

Participants

Reaction Steps

To a solution of 7-fluoro-6-(2-fluoropyridin-3-yl)-2-phenylchroman-4-one (78 mg, 0.23 mmol) in CH2Cl2 (5 mL) under N2 was added TiCl4 (1 M solution in DCM, 1.15 mL, 1.15 mmol) dropwise within 15 minutes at room temperature under dark. After addition, the reaction mixture was stirred for 1 h. To this mixture was added bis-trimethylsilylcarbodiimide (94.3 mg, 0.506 mmol) dropwise. The resulting mixture was stirred overnight. The reaction mixture was poured into ice-water and extracted with DCM. The combined organic phases were dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated to give 7-fluoro-6-(2-fluoro-pyridin-3-yl)-2-phenyl-chroman-4-ylidene-cyanamide (100 mg, 100%).

Provenance & Evidence