Cesium carbonate → 4-(Bromomethyl)-2-methoxypyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of the above compound (0.060 g, 0.14 mmol) in a mixture of 1 mL of THF and 0.15 mL of water under an atmosphere of nitrogen was added 4-(bromomethyl)-2-methoxypyridine hydrobromide (0.048 g, 0.17 mmol), cesium carbonate (0.156 g, 4.80 mmol), and [1,1′-bis-(diphenyl-phosphino)-ferrocene]dichloro-palladium(II), 1:1 complex with dichloromethane (5.0 mg, 0.69 mmol). The mixture was heated at 80° C. for 3 h, cooled to rt, and diluted with dichloromethane. The organic solution was washed with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-5% methanol in dichloromethane to provide the title compound that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 433.2231 for [M+H]+[Calc'd for C23H29N4O3, [M+H]+=433.2234]. 1H NMR (400 MHz, CDCl3) δ 8.91-8.89 (m, 1H), 8.09-8.06 (m, 1H), 7.99-7.97 (m, 2H), 7.37 (dd, J=8.5 Hz, 4.1 Hz, 1H), 6.65 (d, J=5.2 Hz), 6.42 (s, 1H), 4.74-4.60 (m, 2H), 4.37-4.31 (m, 1H), 4.24 (s, 2H), 3.83 (s, 3H), 3.62-3.57 (m, 1H) 3.25 (s, 3H), 2.32-2.30 (m, 1H), 2.18-2.00 (m, 1H), 1.89-1.86 (m, 1H), 1.81-1.74 (m, 2H), 1.59-1.53 (m, 1H), 1.46-1.20 (m, 2H).

Provenance & Evidence