1,4-Dioxane → HCID 136387332, compound

Participants

Reaction Steps

A solution of Pd2(dba)3 (0.012 g, 0.013 mmol) and Me4tBuXPhos (0.012 g, 0.025 mmol) in toluene (2 mL) and dioxane (4 mL) was heated in a screw capped tube (10 mL) at 120° C. for 3 min. The reaction mixture was cooled to RT and the pre-formed catalyst was transferred to a re-sealable pressure tube (50 mL) containing a degassed suspension of Example A8 (0.250 g, 0.628 mmol), 4-methyl imadazole (0.100 g, 1.218 mmol) and potassium phosphate (0.250 g, 1.178 mmol) in a mixture of toluene (4 mL) and dioxane (8 mL) followed by heating at 110° C. for 8 hours. The solids from the reaction mixture was filtered and washed with DCM and THF. The filtrate was completely evaporated and the residue was subjected to chromatography using (0-15% MeOH/DCM) to provide 3-(4-fluorophenyl)-1-(6-methyl-5-((2-(4-methyl-1H-imidazol-1-yl)pyridin-4-yl)oxy)pyridin-2-yl)-1H-1,2,4-triazol-5(4H)-one (0.050 g, 18% yield) as white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.71 (s, 1H), 8.41 (d, J=1.4 Hz, 1H), 8.34 (d, J=5.8 Hz, 1H), 7.98-7.93 (m, 3H), 7.78 (d, J=8.8 Hz, 1H), 7.65 (t, J=1.3 Hz, 1H), 7.48 (br s, 1H), 7.40 (m, 2H), 6.82 (dd, J=5.8, 2.2 Hz, 1H), 2.38 (s, 3H), 2.13 (s, 3H); MS (ESI) m/z: 444.2 (M+H+).

Provenance & Evidence