HCID 67110846, compound → HCID 67111714, compound

HRID 540755Notes

Reaction equation

HRID 540755 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])=[CH:6][C:5]([O:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[N+:24]([O-])=O)=[N:4]1)[CH3:2].[H][H]>CO.[Pt]>[NH2:24][C:18]1[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=1[O:16][C:5]1[CH:6]=[C:7]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])[N:3]([CH2:1][CH3:2])[N:4]=1

Participants

5

Reactant 2

HCID 67110846HCID 67110846, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67111714HCID 67111714, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

Platinum (3% on carbon, poisoned with 0.6% vanadium, 24 mg, 3.8 mmol, 0.005 equiv) was added to a solution of 3-[1-ethyl-3-(4-fluoro-2-nitrophenoxy)-1H-pyrazol-5-yl]benzonitrile (266 mg, 0.755 mmol, 1 equiv) in methanol (7.6 mL). The reaction flask was capped with a three way valve attached to a vacuum line and a hydrogen balloon. The reaction flask was alternately evacuated and charged with hydrogen for 3 cycles, and finally left under an atmosphere of hydrogen at 22° C. The reaction mixture was stirred for 40 minutes, then filtered through celite with the aid of methanol. Concentrated to afford 3-[3-(2-amino-4-fluorophenoxy)-1-ethyl-1H-pyrazol-5-yl]benzonitrile (243 mg, 90% pure) as a light-yellow solid. Calcd (M+1)+: 323.1. Found: 323.0.

Workup

  1. customThe reaction flask was capped with a three way valve
  2. customThe reaction flask was alternately evacuated
  3. additioncharged with hydrogen for 3 cycles
  4. waitfinally left under an atmosphere of hydrogen at 22° C
  5. filtrationfiltered through celite with the aid of methanol
  6. concentrationConcentrated

Sources & evidence

ORD record
ord-37e6b96524a041369fbc692fd30da744
Source dataset
uspto-grants-2014_10
Patent number
US08871796B2

Reaction notes

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