Cesium carbonate → Methyl 3-azido-2-(4-(2-methoxyethoxy)phenyl)-6-(4-methoxyphenyl)isonicotinate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 3-azido-2-(4-hydroxyphenyl)-6-(4-methoxyphenyl)isonicotinate (83 mg, 0.221 mmol), cesium carbonate (359 mg, 1.10 mmol), and 2-bromoethyl methyl ether (0.062 mL, 0.662 mmol) in acetonitrile (1 mL) was heated at 75° C. for 5 hr. The reaction was partitioned between EtOAc and water. The organic phase was separated and washed with brine, dried with sodium sulfate and the solvent removed. Radial silica gel chromatography (step gradient elution with hexane containing 0 to 30% EtOAc) afforded 42 mg of methyl 3-azido-2-(4-(2-methoxyethoxy)phenyl)-6-(4-methoxyphenyl)isonicotinate as an oil. MS (ESI) m/z 435.1 (M+H). 1H NMR (CDCl3) δ ppm 8.02 (2H, d, J=8.55 Hz), 7.93 (1H, s), 7.78-7.86 (2H, m), 7.05 (2H, d, J=8.85 Hz), 6.98 (2H, d, J=8.85 Hz), 4.16-4.24 (2H, m), 4.02 (3H, s), 3.85 (3H, s), 3.75-3.81 (2H, m), 3.47 (3H, s).

Provenance & Evidence