1H-Indazole-5-carbonitrile → 5-(Aminomethyl)-1H-indazole

Temperature

0 °C

To a solution of LiAl H4 (0.76 g, 20.1 mmol) in THF (10 mL) cooled to 0° C. was added a solution of 5-cyanoindazole (0.64 g, 4.47 mmol) in THF (10 mL) dropwise. After 0.5 h the reaction mixture was warmed to reflux for 2 h, then cooled to 0° C. and quenched by the careful addition of water (0.76 mL), 1.0 N sodium hydroxide (0.76 mL), and water (2.28 mL). This mixture was filtered through a pad of celite and washed with THF/MeOH (3:1, 300 mL). Removal of the solvent in vacuo provided a solid which was purified via flash column chromatography (25×150 mm column; elution with MeOH:CH2Cl2:CH2Cl2 saturated with NH3, 10:60:30). This afforded the title compound as a light yellow solid:

1. temperatureAfter 0.5 h the reaction mixture was warmed
2. temperatureto reflux for 2 h
3. customquenched by the careful addition of water (0.76 mL), 1.0 N sodium hydroxide (0.76 mL), and water (2.28 mL)
4. filtrationThis mixture was filtered through a pad of celite
5. washwashed with THF/MeOH (3:1, 300 mL)
6. customRemoval of the solvent in vacuo
7. customprovided a solid which
8. customwas purified via flash column chromatography (25×150 mm column; elution with MeOH:CH2Cl2:CH2Cl2 saturated with NH3, 10:60:30)

ORD record

ord-5002a3a397694005bff0f67d171d89d0

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610692B1