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

HRID 2205819Notes

Reaction equation

HRID 2205819 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-8a12f44189f1496f9eea1992a55f38b0
Source dataset
uspto-grants-2016_06
Patent number
US09371332B2

Reaction notes

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