Cesium carbonate → HCID 70873881, compound

Participants

Reaction Conditions

Reaction Steps

A nitrogen purged suspension of Pd(OAc)2 (77 mg, 0.34 mmol) and 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphane) (430 mg, 0.69 mmol) in 1,4-dioxane (11 ml) was heated at 40° C. for 1 hour. Oxan-4-amine (237 μl, 2.3 mmol), a solution of methyl 2-chloro-3-methylpyridine-4-carboxylate (213 mg, 1.2 mmol) in degassed dioxane (2 ml) and Cs2CO3 (562 mg, 1.7 mmol) were then added and the red suspension was heated at 100° C. for 6 hours. After cooling to room temperature, the mixture was diluted with CH2Cl2 (30 ml) and water (20 ml). The layers were separated and the aqueous phase was extracted with CH2Cl2 (3×15 ml). The combined organic phases were washed with brine (25 ml), dried (MgSO4), filtered and concentrated in-vacuo. The crude residue was purified by column chromatography (25 g SNAP cartridge, Isolera, 0-28% ethyl acetate:heptanes) followed by prep-HPLC (MeCN/Water) to give the title compound (112 mg, 39%) as a white crystalline solid. LC-MS 100%, m/z=251.0; 1H NMR (500 MHz, MeOD) δ ppm 7.91 (d, J=5.20 Hz, 1H) 6.77 (d, J=5.36 Hz, 1H) 4.07-4.17 (m, 1H) 3.98 (dd, J=12.06, 1.81 Hz, 2H) 3.88 (s, 3H) 3.55 (td, J=11.78, 1.66 Hz, 2H) 2.22 (s, 3H) 1.97 (dd, J=12.69, 1.97 Hz, 2H) 1.62 (qd, J=12.03, 4.41 Hz, 2H). NH not observed.

Provenance & Evidence