Pyridine → HCID 59226944, compound

Participants

Reaction Steps

To a solution of 4-cyano-2,3-difluoro-benzoic acid (623 mg, 3.4 mmol) (Example I10) and N,N-dimethylformamide (2 drops) in dichloromethane (17 ml) under a nitrogen atmosphere was added oxalyl chloride (0.3455 ml, 4.08 mmol). The reaction mixture was stirred for one hour at ambient temperature and then at 60° C. for 1.5 hours. The reaction mixture was concentrated and the residue dissolved in tetrahydrofuran (5 ml). The solution was added drop-wise to a solution of 2,6-dimethyl-4-(heptafluoroprop-2-yl)aniline (prepared according to EP 1,006,102) (787 mg, 2.72 mmol) and pyridine (547 μl, 6.8 mmol) in tetrahydrofuran (12 ml). The reaction mixture was stirred at ambient temperature for 16 hours. Then the reaction mixture was poured into aqueous sodium hydrogen carbonate (1M) and the mixture extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by reverse-phase chromatography (eluent: trifluoroacetic acid/water/acetonitrile 1:4:5 to 1:1:8) to give 4-cyano-2,3-difluoro-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-benzamide (0.675 g, 44% yield). 1H-NMR (400 MHz, CDCl3): 2.35 (6H, s), 7.38 (2H, s), 7.57 (1H, m), 7.79 (1H, d), 8.03 (1H, m) ppm.

Provenance & Evidence