Water → 5-Chloro-4-(2-chloropyridin-4-yloxy)-2-fluorobenzenamine

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Reaction Steps

A solution of 4-amino-2-chloro-5-fluorophenol (6.0 g, 37 mmol), 2,4-dichloro-pyridine (5.3 g, 37 mmol) and K2CO3 (5.2 g, 37 mmol) in DMSO (100 mL) was heated at 80° C. under nitrogen overnight. The mixture was cooled to RT, poured into water (300 mL), and extracted with EtOAc (3×200 mL). The combined organics were washed with brine (3×100 mL), dried over Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (EtOAc/petroleum ether) to give 5-chloro-4-(2-chloro-pyridin-4-yloxy)-2-fluoro-phenylamine as a white solid (3.0 g, 32% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.33 (d, J=5.7 Hz, 1 H), 7.34-7.31 (m, 1 H), 7.01-6.82 (m, 3 H), 5.63 (br s, 2 H).

Provenance & Evidence