Hydrazine hydrate (1:1) → 3-[(1E)-2-(1H-indol-6-yl)ethenyl]-5-[(1E)-2-[2-methoxy-4-(2-tetrahydrofuranylmethoxy)phenyl]ethenyl]-1H-pyrazole

HRID 1056812Notes

Reaction equation

HRID 1056812 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[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][CH:25]4[CH2:29][CH2:28][CH2:27][O:26]4)=[CH:19][C:18]=3[O:30][CH3:31])[CH:8]=2)[CH:3]=[CH:2]1.O.[NH2:35][NH2:36]>C(O)(=O)C.C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[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][CH:25]5[CH2:29][CH2:28][CH2:27][O:26]5)=[CH:19][C:18]=4[O:30][CH3:31])[NH:36][N:35]=3)[CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86713212(1E,6E)-1-(1H-indol-6-yl)-7-[2-methoxy-4-(2-tetrahydrofuranylmethoxy)phenyl]hepta-1,6-diene-3,5-dione

Product 1

HCID 665715603-[(1E)-2-(1H-indol-6-yl)ethenyl]-5-[(1E)-2-[2-methoxy-4-(2-tetrahydrofuranylmethoxy)phenyl]ethenyl]-1H-pyrazoleYield 75.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

In 4.5 mL of acetic acid was dissolved 400 mg (0.898 mmol) of (1E,6E)-1-(1H-indol-6-yl)-7-[2-methoxy-4-(2-tetrahydrofuranylmethoxy)phenyl]hepta-1,6-diene-3,5-dione. To this solution was added 0.45 g (9.0 mmol) of hydrazine monohydrate at room temperature and the mixture was stirred at 60° C. for 3 hours. The resulting reaction mixture was diluted with ethyl acetate, washed with a saturated sodium bicarbonate aqueous solution and then 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 298 mg (75% yield) of the title compound as a pale yellowish white powder with the following properties.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with a saturated sodium bicarbonate aqueous solution
  3. dry with materialwith saturated brine, and dried 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-97772031548c447cb6852cb4b4eeb7f0
Source dataset
uspto-grants-2016_07
Patent number
US09399635B2

Reaction notes

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