Aluminium lithium hydride → ({4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}methyl)amine

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Reaction Steps

Lithium aluminium hydride (12.44 ml, 2 M in THF solution, 24.88 mmol) and THF (30 ml) were stirred in an ice bath under argon. A solution of 4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]benzonitrile (1.812 g, 6.22 mmol) in THF (30 ml) was added dropwise over 15 mins. Then the ice bath was removed and the reaction mixture was allowed to stir at room temperature for 1.5 hrs. Then the reaction mixture was cooled using an ice bath and quenched with water dropwise, solvent was removed under vacuo (i.e reduced pressure). Residual material was diluted with DCM and water. Insoluble solid filtered off and organic layer separated, washed with brine, dried over sodium sulphate. The solvent was removed by rotary evaporation. The desired product was isolated using a 25 g SCX column initially washed with DCM (30 ml), DCM/MeOH (60 ml), MeOH (30 ml) and then the desired product was eluted with 1M ammonia in MeOH (25 ml). Solvent evaporated off under reduced pressure to give the title compound as a brown oil (1.563 g, 85%).

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