6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile → (6-Methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methanamine

HRID 475132Notes

Reaction equation

HRID 475132 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:17]#[N:18])[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:9]=2[CH:10]=1>[Ni].N.CO>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[C:4]([CH2:17][NH2:18])[CH:3]=1

Participants

4

Reactant 1

HCID 712724296-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile

Product 1

HCID 71272721(6-Methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methanamineYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

To a solution of 6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (120 mg, 0.5 mmol) in a solution of NH3/MeOH (7 N, 10 mL) was added Raney nickel (50 mg). The mixture was stirred under hydrogen at RT for 2 hours. It was filtered with Celite, and the filtrate was concentrated in vacuo to afford (6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methanamine (113) as brown solid (120 mg, ˜100%). MS (ESI): m/z=246.3 [M+1]+.

Workup

  1. filtrationIt was filtered with Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8bd25e4c3a2a403d871aa831b53cf9a8
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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