Triethylamine → 5-bromo-N-(2-(phenylamino)phenyl)nicotinamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromonicotinic acid (20.0 g, 99 mmol), N-phenyl-o-phenylenediamine (19.32 g, 105 mmol), diisopropylcarbodiimide (DIC) (26.5 g, 210 mmol), and triethylamine (TEA) (2.65 g, 27 mmol) in dichloromethane (DCM) (anhydrous, 350 mL) was heated to 50° C. and degassed with stirring overnight under argon. After cooling to room temperature (RT), the solids were filtered off. The filtrate was washed with water (2×200 mL), dried over sodium sulfate and loaded onto silica gel for purification by a flash chromatography column (gradient of 3% to 10% ethyl acetate in DCM) to yield Compound 1 (30.32 g of material; 83% yield).

Provenance & Evidence