HCID 71272741, compound → HCID 71272561, compound

HRID 475160Notes

Reaction equation

HRID 475160 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[CH:14]=[C:13]([C:16]([F:19])([F:18])[F:17])[CH:12]=[C:11]([C:20]#[N:21])[C:10]=2[CH:9]=[N:8]1>N.[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]([CH2:20][NH2:21])[CH:12]=[C:13]([C:16]([F:17])([F:18])[F:19])[CH:14]=2)[CH:9]=[N:8]1

Participants

4

Reactant 1

HCID 71272741HCID 71272741, compound

Product 1

HCID 71272561HCID 71272561, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

To a solution of 1-(tetrahydro-2H-pyran-2-yl)-6-(trifluoromethyl)-1H-indazole-4-carbonitrile (440 mg, 1.49 mmol) in ammonia (2M solution in methanol, 10 mL) was added Raney-Ni (1.27 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 (1-(tetrahydro-2H-pyran-2-yl)-6-(trifluoromethyl)-1H-indazol-4-yl)methanamine (127, 267 mg, yield: 60%). MS (ESI) m/z: 300.2 [M+1]+.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ead9d1977c694c6eae12d403c939f94c
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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