Cesium carbonate → HCID 136387314, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of Example A8 (0.250 g, 0.628 mmol), cyclopropane carboxamide (0.100 g, 1.175 mmol), Cs2CO3 (0.400 g, 1.228 mmol) and X-Phos (0.012 g, 0.025 mmol) in dioxane (20 mL) was purged with argon for 5 minutes. To the reaction mixture was added Pd2(dba)3 (0.012 g, 0.013 mmol) and the mixture wass heated in a reclosable sealed tube (100 mL) at 110° C. for 8 h. The solids from the reaction mixture was filtered and washed with DCM and THF. The filtrate was evaporated and the residue subjected to chromatography using (0-100% EtOAc/DCM) to provide N-(4-((6-(3-(4-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)-2-methylpyridin-3-yl)oxy)pyridin-2-yl)cyclopropanecarboxamide (0.072 g, 24%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 12.73 (s, 1H), 10.89 (s, 1H), 8.21 (d, J=5.7 Hz, 1H), 7.98-7.93 (m, 3H), 7.75 (d, J=8.8 Hz, 1H), 7.59 (d, J=2.4 Hz, 1H), 7.40 (t, J=8.8 Hz, 2H), 6.71 (dd, J=5.7, 2.4 Hz, 1H), 2.33 (s, 3H), 1.95 (t, J=6.1 Hz, 1H), 0.75 (d, J=6.2 Hz, 4H), MS (ESI) m/z: 447.2 (M+H+).

Provenance & Evidence