Potassium tert-butoxide → HCID 15117076, compound

HRID 655014Notes

Reaction equation

HRID 655014 reaction equation
[C:1]1([NH:7][N:8]=[C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2F)[N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+]>O1CCCC1>[C:1]1([N:7]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:9]([N:10]3[CH2:15][CH2:14][N:13]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:12][CH2:11]3)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 54137959HCID 54137959, compound

Product 1

HCID 15117076HCID 15117076, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution, under nitrogen, of 9.1 g of 1-[(phenylhydrazono)(2-fluorophenyl)methyl]-4-phenylpiperazine in 100 ml of tetrahydrofuran was added, dropwise, a solution of 3.3 g of potassium t-butoxide in 35 ml of tetrahydrofuran. The reaction mixture was stirred at ambient temperature for 4 hours and concentrated. The concentrate was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated to a solid. The solid was flash chromatographed on silica gel utilizing hexane/ethyl acetate (30%) as the eluent. Concentration of the appropriate fractions followed by recrystallization from ethyl acetate/hexane gave 2.1 g (25%) of 1-phenyl-3-(4-phenyl-1-piperazinyl)-1H-indazole, mp 129-130°.

Workup

  1. concentrationconcentrated
  2. additionThe concentrate was diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated to a solid
  7. customchromatographed on silica gel
  8. customConcentration of the appropriate fractions followed by recrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-89ba5cbe5db840dcbceb4d2ff5d6d2e7
Source dataset
uspto-grants-1992_07
Patent number
US05134236

Reaction notes

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