Diethyl Ether → HCID 86663041, compound

Participants

Reaction Steps

Methyl 3-amino-6-bromo-2-(4-chlorophenyl)isonicotinate (3.86g, 11 3 mmol) was dissolved in TFA (57 mL) and the solution was cooled in an ice bath. Solid sodium nitrite (1.72 g, 24 9 mmol) was added slowly with stirring to give a brown solution with gas evolution. After 30 min solid sodium azide (7.35 g, 113 mmol) was added in portions over 5 min with gas evolution. Et2O (57 mL) was slowly added and a precipitate formed. After stirring for 0.5 h, water was added and the mixture was extracted with EtOAc. The combined organic phases were washed with water (3×) and brine (1×) and then saturated aqueous Na2CO3 solution (so that the aqueous phase was basic) and brine (1×). After drying with sodium sulfate, the solvent was removed to leave methyl 3-azido-6-bromo-2-(4-chlorophenyl)isonicotinate (2.41 g, 6.56 mmol, 58.0% yield) as a fluffy yellow solid. 1 H NMR (400 MHz, chloroform-d) δ ppm 7.79 (1H, s), 7.68-7.73 (2H, m), 7.42-7.47 (2H, m), 4.00 (3H, s).

Provenance & Evidence