Cesium carbonate → HCID 90410934, compound

Participants

Reaction Steps

A suspension of Example A1 (2.00 g, 7.95 mmol), Cs2CO3 (5.00 g, 15.35 mmol), X-Phos (0.200 g, 0.420 mmol), Pd2(dba)3 (0.200 g, 0.218 mmol) and isobutyramide (1.00 g, 11.48 mmol) in dioxane (20 mL), under Ar, was heated at 90° C. overnight. The mixture was cooled to RT, the solids removed via filtration, washed with DCM and THF and the filtrate concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(4-((6-nitropyridin-3-yl)oxy)pyridin-2-yl)isobutyramide (1.08 g, 45%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 10.65 (s, 1H), 8.58 (m, 1H), 8.41 (dd, J=8.9, 0.5 Hz, 1H), 8.31 (d, J=5.7 Hz, 1H), 7.99 (dd, J=8.9, 2.8 Hz, 1H), 7.85 (d, J=2.4 Hz, 1H), 6.89 (dd, J=5.7, 2.4 Hz, 1H), 2.72 (m, 1H), 1.03 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 303.1 (M+H+).

Provenance & Evidence