4-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole → 1-(Tetrahydro-2H-pyran-4-YL)-1H-pyrazol-4-amine
Reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:8]=1)([O-])=O>CO.[Pd]>[O:12]1[CH2:11][CH2:10][CH:9]([N:7]2[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]2)[CH2:14][CH2:13]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 4-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole (568 mg, 2.88 mmol, 1 equiv) in methanol was circulated through a H-Cube® Continuous-flow hydrogenation reactor (ThalesNano) fitted with a palladium on carbon catalyst cartridge at 50° C. The collected solution was concentrated in vacuo to afford product as pink solid (458 mg, 95% yield). LCMS (ESI) m/z: 168.0.
Workup
- concentrationThe collected solution was concentrated in vacuo
Sources & evidence
- ORD record
- ord-70bae89315f14c35bf0aa6bb6e2e96bd
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434732B2
Reaction notes
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