Ethyl Acetate → HCID 71184874, compound

HRID 1629969Notes

Reaction equation

HRID 1629969 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([N:7]1[CH2:11][CH2:10][C:9]([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[C:15]#N)=[N:8]1)=[O:6].CCOC(C)=O>CCO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:5]([N:7]2[CH2:11][CH2:10][C:9]([C:12]3[CH:13]=[C:14]([CH3:15])[CH:17]=[CH:18][CH:19]=3)=[N:8]2)=[O:6])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 71184873HCID 71184873, compound

Product 1

HCID 71184874HCID 71184874, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-[1-(3-Fluoro-benzoyl)-4,5-dihydro-1H-pyrazol-3-yl]-benzonitrile (88 mg, 0.30 mmol), dissolved in EtOH (10 mL) and EtOAc (10 mL) was passed through the H-cube equipped with a 10% Pd/C cartridge. Temperature 80° C., 50 bar, flow rate, 1 mL/min. LC-MS showed consumption of SM. The solvent was evaporated under pressure and the material was purified by chromatography using a 12 g silica cartridge eluting with heptane-EtOAc, gradient 0 to 50% EtOAc. Amount obtained: 30 mg, 0.11 mmol, 35% yield. LC-MS (ESI) m/e 283 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.40 (s, 3H) 3.26-3.33 (m, 2 H) 4.27 (t, J=9.96 Hz, 2 H) 7.17-7.26 (m, 2 H) 7.32 (t, J=7.81 Hz, 1H) 7.43 (td, J=7.98, 5.81 Hz, 1H) 7.49-7.54 (m, 2 H) 7.73-7.84 (m, 2 H).

Workup

  1. customTemperature 80° C., 50 bar, flow rate, 1 mL/min
  2. customconsumption of SM
  3. customThe solvent was evaporated under pressure
  4. customthe material was purified by chromatography
  5. washeluting with heptane-EtOAc, gradient 0 to 50% EtOAc
  6. customAmount obtained

Sources & evidence

ORD record
ord-589143b3eee541b89fb8135cb212762f
Source dataset
uspto-grants-2014_07
Patent number
US08791114B2

Reaction notes

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