Acetamide → HCID 90425939, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-((2-chloropyridin-4-yl)oxy)-6-iodo-2,4-dimethylpyridine (1.45 g, 4.02 mmol), acetamide (950 mg, 16.09 mmol), Cs2CO3 (1.965 g, 6.03 mmol) and X-phos (96 mg, 0.201 mmol) in dioxane (25 mL) was sparged with Ar, treated with Pd2(dba)3 (184 mg, 0.201 mmol), sparged again with Ar and heated at 85° C. overnight. The mixture was cooled to RT, diluted with EtOAc and the solids removed via filtration through diatomaceous earth. The filtrate was washed with water, then brine, dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(5-((2-chloropyridin-4-yl)oxy)-4,6-dimethylpyridin-2-yl)acetamide (598 mg, 51%). 1H NMR (400 MHz, DMSO-d6): δ 10.53 (s, 1 H), 8.26 (d, J=5.8 Hz, 1 H), 7.94 (s, 1 H), 6.99 (d, J=2.3 Hz, 1 H), 6.85 (dd, J=5.8, 2.3 Hz, 1 H), 2.17 (s, 3 H), 2.06 (d, J=1.7 Hz, 6 H); MS (ESI) m/z: 292.1 (M+H+).

Provenance & Evidence