Dichloromethane → 1,5-Anhydro-2,3-dideoxy-3-{[(4-{[6-(1-methyl-1H-pyrazol-4-yl)pyridine-3-yl]methyl}-5,6,7,8-tetrahydroquinolin-2-yl)carbonyl}amino]-L-threo-pentitol

Participants

Reaction Steps

To a solution of 1,5-anhydro-3-[({4-[(6-chloropyridin-3-yl)methyl]-5,6,7,8-tetrahydroquinolin-2-yl}carbonyl)amino]-2,3-dideoxy-L-threo-pentitol (Example 1, 0.081 g, 0.20 mmol) in a mixture of 2 mL of THF and 0.2 mL of water under an atmosphere of nitrogen was added cesium carbonate (0.197 g, 0.605 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.050 g, 0.24 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II), 1:1 complex with dichloromethane (0.016 g, 0.020 mmol). The reaction was irradiated in a microwave reactor at 100° C. for 30 min, cooled to rt, and diluted with ethyl acetate. The mixture was filtered through celite, concentrated in vacuo, and purified via silica gel chromatography, eluting with 1-6% methanol in dichloromethane, to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 448.0 for [M+H]+: 1H NMR (400 MHz, d6-DMSO) δ 8.38 (s, 1H), 8.31 (d, J=8.2 Hz, 1H), 8.25 (s, 1H), 7.97 (s, 1H), 7.62-7.54 (m, 3H), 4.03 (br s, 2H), 3.88 (s, 2H), 3.82-3.71 (m, 3H), 3.59-3.52 (m, 1H), 3.41-3.29 (m, 2H), 3.04-2.99 (m, 1H), 2.91 (br s, 2H), 2.74 (br s, 2H), 1.85 (br s, 1H), 1.80 (s, 3H), 1.65-1.55 (m, 1H), 1.11-1.07 (m, 1H).

Provenance & Evidence