Reacción #1350617

Ecuación de reacción

NaOH

LiAlH4

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

compound 94

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

Ethyl acetate

→

amine

Rendimiento 92.0%

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

Rendimiento 92.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to room temperature
2. 2
   Filtraciónthe suspension was filtered (Celite)
3. 3
   LavadoThe filter cake was washed with an addition portion of ethyl acetate (40 mL)
4. 4
   OtroCombined organic layers were evaporated under vacuum

Procedimiento

A solution of LiAlH4 (Aldrich, 10.5 mL, 10.5 mmol, 1.0 M) in THF was added dropwise into a yellow solution of 5-(azidomethyl)-1-(2-tetrahydropyranyl)indazole (compound 94, 2.6 g, 10.1 mmol) in THF (30 mL) at 0° C. The addition time was 10 minutes and gas was released. After stirring at 0° C. for 1 hour, NaOH (1.0M, 1.5 mL) was added. The reaction mixture was allowed to warm to room temperature. Ethyl acetate (100 mL) was added, and the suspension was filtered (Celite). The filter cake was washed with an addition portion of ethyl acetate (40 mL). Combined organic layers were evaporated under vacuum to give free amine 63 (2.14 g, 92%). MS (electrospray) 232.5 (M+1); 1H NMR (CDCl3) δ1.61 (m, 3H), 2.02 (m, 2H), 2.50 (m, 1H), 2.83 (br s, 2H), 3.68 (m, 1H), 3.85 (s, 2H), 3.95 (m, 1H), 5.62 (d, 1H, J=9.2 Hz), 7.29 (d, 1H, J=8.8 Hz), 7.48 (d, 1H, J=8.8 Hz), 7.53 (s, 1H), 7.92 (s, 1H).

Fuente