HCID 58958600, compound → HCID 58958580, compound

HRID 915574Notes

Reaction equation

HRID 915574 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH:13]=[CH2:14])=[C:11]([NH2:15])[N:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])[N:9]=2)=[CH:4][CH:3]=1>[Pd].CCO>[CH2:13]([C:12]1[C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:9][N:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])[C:11]=1[NH2:15])[CH3:14]

Participants

4

Reactant 1

HCID 58958600HCID 58958600, compound

Product 1

HCID 58958580HCID 58958580, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a mixture of wet palladium on carbon (10 wt %, 10 mg) in EtOH (5 mL) was added 3-(4-fluorophenyl)-1-(2-methylphenyl)-4-vinyl-1H-pyrazol-5-amine (87 mg, 0.30 mmol) in EtOH (5 mL). The reaction was mixed on a Parr shaker under H2 atmosphere (55 psi) for 16 h. The palladium catalyst was filtered through Celite® and rinsed with EtOH (3×20 mL). The solution was concentrated under reduced pressure to afford the title compound (68 mg, 77%) containing trace impurities. This material was used in subsequent reactions without further purification: ES-MS m/z 296.2 (MH+); HPLC RT (min) 2.65.

Workup

  1. additionThe reaction was mixed on a Parr shaker under H2 atmosphere (55 psi) for 16 h
  2. filtrationThe palladium catalyst was filtered through Celite®
  3. washrinsed with EtOH (3×20 mL)
  4. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ecaf9d763839454ea6c63e87bdbbdf54
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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