Ammonia → 4-aminomethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]#[N:17])[C:10]=2[CH:9]=[N:8]1.N>CO.[Ni]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[C:11]([CH2:16][NH2:17])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[N:8]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 198 (430 mg, 1.89 mmol) in a 7N solution of NH3 in MeOH (20 mL) was added Raney nickel (50 mg), and the mixture was stirred under hydrogen (1 atm) at RT overnight. The Raney nickel was removed by filtration. The filtrate was concentrated to afford 340 mg (79%) of (1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl) methanamine (199) as yellow syrup: MS (ESI) m/z=232.2 [M+1]+.