3,5-Dimethylaniline → N-(3,5-Dimethylphenyl)-2-(2-fluoropyridin-4-ylmethylthio)pyridine-3-carboxamide

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Reaction Steps

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (3.0 g, 7.9 mmol) was added to a solution of 2-(2-fluoropyridin-4-ylmethylthio)pyridine-3-carboxylic acid (Reference compound No. 2-1, 1.5 g, 5.7 mmol), 3,5-xylidine (0.90 g, 7.4 mmol) and N,N-diisopropylethylamine (2.0 mL, 11 mmol) in N,N-dimethylformamide (20 mL) at room temperature, and the mixture was stirred for 12 hours. Ethyl acetate (30 mL) was added to the reaction mixture, the whole was washed with brine (50 mL), and then the organic layer was dried over anhydrous magnesium sulfate. The organic layer was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 0.91 g of the title reference compound as a colorless solid. (Yield 44%)

Provenance & Evidence