Ethyl Acetate → HCID 90425921, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 6-iodo-2,4-dimethylpyridin-3-ol (5.10 g, 20.48 mmol) in DMA (60 mL) was sparged with Ar, treated with 2,4-dichloropyridine (3.94 g, 26.60 mmol) and K2CO3 (3.40 g, 24.57 mmol) and heated at 105° C. overnight. The mixture was cooled to RT, treated with EtOAc and water, filtered to remove solids, then treated with charcoal, warmed to reflux, cooled to RT and filtered through diatomaceous earth. The layers of the filtrate were separated, the aqueous layer extracted with additional EtOAc (1×) and the combined organics were washed with brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 3-((2-chloropyridin-4-yl)oxy)-6-iodo-2,4-dimethylpyridine (1.476 g, 20%). 1H NMR (400 MHz, DMSO-d6): δ 8.27 (d, J=5.8 Hz, 1 H), 7.75 (s, 1 H), 7.05 (d, J=2.3 Hz, 1 H), 6.89 (dd, J=5.8, 2.3 Hz, 1 H), 2.20 (s, 3 H), 2.02 (s, 3 H); MS (ESI) m/z: 361.0 (M+H+).

Provenance & Evidence