Cesium carbonate → HCID 53236425, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[(5-bromopyridin-2-yl)methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]-4-oxo-4H-quinolizine-3-carboxamide (Example 2, 0.045 g, 0.099 mmol) in 2 mL of THF under an atmosphere of nitrogen was added aqueous cesium carbonate (1 N, 0.20 mL, 0.20 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.062 g, 0.30 mmol), and bis(tri-tert-butylphosphine)palladium(0) (5.0 mg, 0.010 mmol). The reaction was heated at 100° C. for 15 h, cooled to rt, and concentrated in vacuo. The resultant residue was subjected to purification via reverse phase HPLC to provide the title compound that gave a proton NMR spectra consistent with theory and a high resolution mass spectrum (ES+) m/z of 472.2330 calculated for M+H+ [C27H30N5O3: 472.2343]: 1H NMR (400 MHz, CD3OD) δ 9.50 (d, J=7.0 Hz, 1H), 8.83 (s, 1H), 8.53-8.50 (m, 1H), 8.35-8.30 (m, 1H), 8.16 (s, 1H), 8.06-7.97 (m, 2H), 7.88 (d, J=8.0 Hz, 1H), 7.56 (d, J=8.2 Hz, 1H), 7.52-7.48 (m, 1H), 4.62 (s, 2H), 3.95 (s, 3H), 3.86-3.81 (m, 1H), 3.55-3.48 (m, 1H), 3.21-3.12 (m, 1H), 2.13-2.10 (m, 1H), 2.03-1.87 (m, 1H), 1.79-1.73 (m, 2H), 1.40-1.24 (m, 3H).

Provenance & Evidence