4-Aminopyridine → 2,4,6-trichloro-N-(pyridin-4-yl)benzamide

Participants

Reaction Steps

A mixture of 2,4,6-trichlorobenzoic acid (224 mg, 10 mmol), 4-aminopyridine (141 mg, 1.5 mmol), HATU (1140 mg, 3 mmol), and DIPEA (646 mg, 5 mmol) in 5 mL anhydrous DMF was stirred under nitrogen at room temperature overnight. The reaction mixture was poured into ice-water (20 mL) and extracted EtOAc (2×50 mL). The combined organics were evaporated to dryness in vacuum and the residue was purified by silica gel column chromatography (EtOAc) to afford the desired product (72 mg, yield: 24%). 1HNMR: (CD3OD-d4, 400 MHz): δ 8.38 (d, J=6.0 Hz, 2H), 7.65 (d, J=6.0 Hz, 2H), 7.52 (s, 2H). LCMS (ESI) m/z: 301.1 [M+H+].

Provenance & Evidence