Potassium Phosphate, Tribasic → HCID 86270036, compound

Participants

Reaction Steps

A solution of Pd2(dba)3 (10.12 mg, 0.011 mmol) and Me4t-BuXPhos (0.012 g, 0.025 mmol) in toluene (0.2 mL) and dioxane (0.4 mL) was heated at 120° C. for 3 min, cooled to RT, added to a degassed suspension of N-(5-((2-chloropyridin-4-yl)oxy)-4-methylpyridin-2-yl)-3-methyl-2-oxoimidazolidine-1-carboxamide (0.1 g, 0.276 mmol), 4-methyl imidazole (0.030 g, 0.359 mmol) and K3PO4 (0.117 g, 0.553 mmol) in toluene (0.4 mL) and dioxane (0.8 mL) and heated at 110° C. overnight. The mixture was treated with additional catalyst (synthesized from Pd2(dba)3 (10.12 mg, 0.011 mmol) and Me4t-BuXPhos (0.012 g, 0.025 mmol) in toluene (0.2 mL) and dioxane (0.4 mL) as above) and heated at 110° C. overnight. The mixture was cooled to RT, treated with satd. NaHCO3, extracted with EtOAc (5×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified twice via silica gel chromatography (MeOH/DCM). The material was treated with MeCN, heated to reflux, cooled to RT and the resulting solid collected via filtration and dried to afford 3-methyl-N-(4-methyl-5-((2-(4-methyl-1H-imidazol-1-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-oxoimidazolidine-1-carboxamide (20 mg, 17%). 1H NMR (400 MHz, DMSO-d6): δ 10.92 (s, 1 H), 8.39 (d, J=1.4 Hz, 1 H), 8.30 (d, J=5.8 Hz, 1 H), 8.13 (s, 1 H), 8.02 (s, 1 H), 7.64 (t, J=1.3 Hz, 1 H), 7.33 (d, J=2.2 Hz, 1 H), 6.73 (dd, J=5.8, 2.2 Hz, 1 H), 3.79-3.78 (m, 2 H), 3.46-3.44 (m, 2 H), 2.80 (s, 3 H), 2.15 (s, 3 H), 2.13 (s, 3H); MS (ESI) m/z: 408.2 (M+H+).

Provenance & Evidence