Diethyl Ether → HCID 86663059, compound

Participants

Reaction Steps

Methyl 3-amino-6-bromo-2-(4-morpholinophenyl)isonicotinate (2.0 g, 5.1 mmol) was quickly dissolved in TFA (25 mL) and the light brown solution was cooled in an ice-bath. Solid sodium nitrite (0.405 g, 5.86 mmol) was added in small portions over 5 min with stirring to give a dark red mixture. After 30 min, solid sodium azide (1.24 g, 19.1 mmol) was added over 1 min followed by Et2O (25 mL). The mixture was stirred in the ice-bath for 30 min. Water was added and the mixture was extracted with EtOAc. The combined organic phases were washed with water (3×), brine, sat. aq. NaHCO3 solution (until aq. phases were basic), and brine (1×). After drying with sodium sulfate, the solvent was removed and silica gel chromatography (step gradient elution with hexane containing 5, 10, 15, 20% EtOAc) to afford methyl 3-azido-6-bromo-2-(4-morpholinophenyl)isonicotinate (1.27 g, 3.04 mmol, 60% yield) as a solid. 1H NMR (500 MHz, chloroform-d) δ ppm 7.77 (2H, d, J=9.16 Hz), 7.70 (1H, s), 6.99 (2H, d, J=9.16 Hz), 4.02 (3H, s), 3.87-3.92 (4H, m), 3.26-3.31 (4H, m).

Provenance & Evidence