Reacción #1350616

Ecuación de reacción

water

5-(bromomethyl)-1-(2-tetrahydropyranyl)indazole

compound 93

5-(bromomethyl)-1-(2-tetrahydropyranyl)indazole

sodium azide

→

product ( 94 )

Rendimiento 99.5%

5-(azidomethyl)-1-(2-tetrahydropyranyl)indazole

Rendimiento 99.5%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroa yellow solution formed
2. 2
   TemperaturaAfter cooling to room temperature
3. 3
   Extracciónextracted with ether (2×150 mL)
4. 4
   LavadoCombined organic layers were washed with brine
5. 5
   Secadodried (MgSO4)
6. 6
   OtroEvaporation of solvent

Procedimiento

To a solution of 5-(bromomethyl)-1-(2-tetrahydropyranyl)indazole (compound 93, 3.0 g, 10.2 mmol) in DMF (30 mL), was added with sodium azide (Aldrich, 2.64 g, 40.6 mmol) in one portion. The suspension was heated at 90° C. for 30 minutes and a yellow solution formed. After cooling to room temperature, the reaction mixture was poured into water (100 mL) and extracted with ether (2×150 mL). Combined organic layers were washed with brine, then dried (MgSO4). Evaporation of solvent gave the product (94) as a yellow oil (2.61 g, 99%). TLC Rf 0.63 (60:40 hexane-ethyl acetate); MS (electrospray) 258 (M+1); 1H NMR (CDCl3) δ2.03-2.15 (m, 2H), 2.55 (m, 1H), 3.72 (m, 1H), 4.02 (m, 1H), 4.52 (s, 1H), 5.71 (d, 1H, J=9.4 Hz), 7.32 (d, 1H, J=8.8 Hz), 7.56 (d, 1H, J=8.8 Hz), 7.63 (s, 1H), 8.00 (s, 1H).

Fuente