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

HRID 475142Notes

Reaction equation

HRID 475142 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[C:10]([C:12]#[N:13])=[CH:9][CH:8]=[CH:7][C:6]=2[N:5]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[N:4]=1>[Ni].N.CO>[CH3:1][O:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:12][NH2:13])[N:5]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][O:15]2)[N:4]=1

Participants

4

Reactant 1

HCID 712722393-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile

Product 1

HCID 71272469(3-Methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methanamineYield 91.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A mixture of 3-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (140 mg, 0.544 mmol) and Raney nickel (20 mg) in NH3/MeOH (7N, 10 mL) was stirred under hydrogen overnight. The reaction mixture was filtered with Celite® and the filtrate concentrated in vacuo to afford (3-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methanamine as an oil (119) 130 mg, 91.4%). MS (ESI): m/z=262 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered with Celite®
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-8f4beb6792964960bf95b2d557ad83e6
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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