Ethanol → 3-(3-fluorophenyl)-4-(2-phenylethynyl)-1H-pyrazol-5-amine

HRID 588616Notes

Reaction equation

HRID 588616 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[C:11]([NH:21]C(=O)C)[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(O)C.[OH-].[Na+]>C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]#[C:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[C:11]([NH2:21])[NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 178474488HCID 178474488, compound

Product 1

HCID 1785091073-(3-fluorophenyl)-4-(2-phenylethynyl)-1H-pyrazol-5-amineYield 69.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-[3-(3-fluorophenyl)-4-(2-phenylethynyl)-1H-pyrazol-5-yl]acetamide (2 g, 6.2 mmol), ethanol (22 mL) and 25% aq. NaOH solution (22 mL) was stirred and heated to 80° C. for 1 h and cooled to room temperature. The reaction mixture was diluted with ethyl acetate and water. The organic phase was washed with water and brine, dried (phase separator cartridge) and concentrated in vacuo, to provide the title compound as a solid (1.2 g).

Workup

  1. temperaturecooled to room temperature
  2. washThe organic phase was washed with water and brine
  3. customdried (phase separator cartridge)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c5fceb3c465488cb1b57db898e23899
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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