Cesium carbonate → HCID 66742549, compound

Participants

Reaction Conditions

Reaction Steps

A flask containing 2-(6-amino-pyridin-3-yloxy)-2-methyl-propionic acid ethyl ester (1.365 g, 6.09 mmol), 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one (1.77 g, 7.91 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (528 mg, 0.913 mmol) and cesium carbonate (6.94 g, 21.3 mmol) in dry dioxane (60 ml) was evacuated under vacuum and back filled with argon (repeat 3 times). Tris(dibenzylideneacetone)dipalladium (0) (418 mg, 0.457 mmol) was added and the flask evacuated under vacuum and back filled with argon (repeat 3 times). The flask was place in an oil bath heated to 90° C. and stirred for 16 hours under argon atmosphere. The flask was cooled to ambient and the material was filtered through a plug of celite, rinsing well with dioxane. The volatiles were concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 5% to 25% ethyl acetate/hexane to provide the desired product as a light yellow-brown powder (2.035 g). (M+H)+=367 m/e. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.30 (t, J=7.18 Hz, 3 H) 1.59 (s, 6 H) 3.80 (s, 3 H) 4.26 (q, J=7.18 Hz, 2 H) 6.83 (d, J=9.06 Hz, 1 H) 7.26-7.30 (m, 1 H) 8.04 (d, J=3.02 Hz, 1 H) 8.18 (s, 1 H) 8.22 (s, 1 H).

Provenance & Evidence