Triethylamine → 3-(Azidocarbonyl)-2-chloropyridine

Temperatur

0 °C

To a solution of 2-chloronicotinic acid (1.0 g, 6.35 mmol) in a mixture of acetone (14 mL) and water (6 mL) was added triethylamine (0.97 mL, 6.98 mmol). The mixture was cooled to 0° C. in a ice-bath. Ethylchloroformate (1.03 g, 9.5 mmol) was then added and the resulting mixture was stirred for 1.0 hour at 0° C. To the mixture was added sodium azide (0.70 g, 10.8 mmol), and the mixture was stirred for another 3 hours. The mixture was concentrated, the residue was diluted with dichloromethane and washed with water. The organic layer was dried over MgSO4 and concentrated to give desired product (550 mg, 48%). 1HNMR (CDCl3) (δ) 8.57 (d, 1H), 8.22 (d, 1H), 7.37 (t, 1H).

1. stirringthe mixture was stirred for another 3 hours
2. concentrationThe mixture was concentrated
3. additionthe residue was diluted with dichloromethane
4. washwashed with water
5. dry with materialThe organic layer was dried over MgSO4
6. concentrationconcentrated

ORD-Eintrag

ord-2c1c739b239049bca928398ae3b7e3dc

Quelldatensatz

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06608077B2