3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile → (3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methanamine

HRID 475123Notes

Reaction equation

HRID 475123 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[N:3]=1>N.CO.[Ni]>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][NH2:12])[N:4]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[N:3]=1

Participants

4

Reactant 1

HCID 712722493-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile

Product 1

HCID 71272763(3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methanamineYield 91.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

To a solution of 3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (130 mg, 0.54 mmol) in NH3/MeOH (7N, 10 mL) was added Raney nickel (20 mg). The mixture was stirred under hydrogen overnight. The reaction mixture was filtered, and the filtrate was concentrated to afford (3-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methanamine (120 mg, 91.5%). MS (ESI): m/z=246 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f9d1859ead324f5d803e9bab1dd901d2
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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