Hydrazine hydrate (1:1) → 3-[(1E)-2-(1H-indol-5-yl)ethenyl]-5-[(1E)-2-[4-(2-pyridylmethoxy)phenyl]ethenyl]-1H-pyrazole

HRID 1056818Notes

Reaction equation

HRID 1056818 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6](/[CH:10]=[CH:11]/[C:12](=O)[CH2:13][C:14](=O)/[CH:15]=[CH:16]/[C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=4)=[CH:19][CH:18]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.O.[NH2:34][NH2:35]>C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6](/[CH:10]=[CH:11]/[C:12]3[CH:13]=[C:14](/[CH:15]=[CH:16]/[C:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=5)=[CH:19][CH:18]=4)[NH:35][N:34]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86713216(1E,6E)-1-(1H-indol-5-yl)-7-[4-(2-pyridylmethoxy)phenyl]hepta-1,6-diene-3,5-dione

Product 1

HCID 665716143-[(1E)-2-(1H-indol-5-yl)ethenyl]-5-[(1E)-2-[4-(2-pyridylmethoxy)phenyl]ethenyl]-1H-pyrazoleYield 24%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

In 0.34 mL of acetic acid was dissolved 15 mg (35 μmol) of (1E,6E)-1-(1H-indol-5-yl)-7-[4-(2-pyridylmethoxy)phenyl]hepta-1,6-diene-3,5-dione. To this solution was added 34 μL (0.70 mmol) of hydrazine monohydrate at room temperature and the mixture was stirred at 60° C. for 3 hours. The reaction mixture was neutralized with a saturated sodium bicarbonate aqueous solution and extraction with ethyl acetate was performed. The resulting organic layer was washed with saturated brine and dried over magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate or methylene chloride/methanol). The resulting solid was washed with an organic solvent to give 3.5 mg (24% yield) of the title compound as a pale yellowish white powder with the following properties.

Workup

  1. extractionThe reaction mixture was neutralized with a saturated sodium bicarbonate aqueous solution and extraction with ethyl acetate
  2. washThe resulting organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate or methylene chloride/methanol)
  7. washThe resulting solid was washed with an organic solvent

Sources & evidence

ORD record
ord-1e93aab32cbb474b83513f1d853f681b
Source dataset
uspto-grants-2016_07
Patent number
US09399635B2

Reaction notes

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