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

HRID 475163Notes

Reaction equation

HRID 475163 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:18]#[N:19])[C:6]2[CH:7]=[N:8][N:9]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[C:10]=2[CH:11]=1>N.[Ni]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[N:8][N:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[C:5]([CH2:18][NH2:19])[CH:4]=1

Participants

4

Reactant 1

HCID 866947116-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile

Product 1

HCID 71272219(6-Methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methanamineYield 76%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

To a solution of 6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile (350 mg, 1.36 mmol) in ammonia (2M solution in methanol, 15 mL) was added Raney-Ni (1.17 g, suspension in water). The mixture was stirred under a hydrogen atmosphere (1 atm.) at RT for 16 h and then filtered. The filtrate was concentrated in vacuo to afford crude (6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-4-yl)methanamine (129, 270 mg, yield: 76%). MS (ESI) m/z: 262.4 [M+1]+.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2f10ab0f66a949c69165537d1d138b89
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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