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Triphenylphosphine → 7-(4-fluorophenyl)-7-methoxy-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazole

HRID 2235750
Notes
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Reaction equation

HRID 2235750 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([O:52][CH3:53])([C:31]2[NH:32][N:33]=[C:34](/[CH:36]=[CH:37]/[C:38]3[CH:43]=[CH:42][C:41]([N:44]4[CH:48]=[C:47]([CH3:49])[N:46]=[CH:45]4)=[C:40]([O:50][CH3:51])[CH:39]=3)[N:35]=2)[CH2:28][CH2:29]O)=[CH:23][CH:22]=1>C(Cl)(Cl)(Cl)Cl.C1COCC1>[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([O:52][CH3:53])[C:31]3[N:32]([N:33]=[C:34](/[CH:36]=[CH:37]/[C:38]4[CH:43]=[CH:42][C:41]([N:44]5[CH:48]=[C:47]([CH3:49])[N:46]=[CH:45]5)=[C:40]([O:50][CH3:51])[CH:39]=4)[N:35]=3)[CH2:29][CH2:28]2)=[CH:23][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 670672233-(4-fluorophenyl)-3-methoxy-3-(5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-2H-[1,2,4]triazol-3-yl)propan-1-ol

Product 1

HCID 592997037-(4-fluorophenyl)-7-methoxy-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-6,7-dihydro-5H-pyrrolo[1,2-b][1,2,4]triazoleYield 1.9%

Reagents, catalysts & solvents 2

HCID 5943
Carbon Tetrachloride
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (22 mg) was added to a suspension of 3-(4-fluorophenyl)-3-methoxy-3-(5-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-2H-[1,2,4]triazol-3-yl)propan-1-ol (38 mg) in carbon tetrachloride (2 mL) and THF (2 mL), and the reaction solution was heated under reflux for seven hours. The reaction solution was left to cool to room temperature and concentrated under reduced pressure. Ethyl acetate and a saturated sodium bicarbonate solution were added to the resulting residue, and the organic layer was separated. The organic layer washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane-ethyl acetate system), again purified with silica gel column chromatography (elution solvent: ethyl acetate-methanol system) and then purified by LC-MS. After concentrating the target fraction, ethyl acetate and a saturated sodium bicarbonate solution were added to the residue, and the organic layer was separated. The organic layer washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 0.69 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureunder reflux for seven hours
  3. waitThe reaction solution was left
  4. concentrationconcentrated under reduced pressure
  5. additionEthyl acetate and a saturated sodium bicarbonate solution were added to the resulting residue
  6. customthe organic layer was separated
  7. washThe organic layer washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (carrier: Chromatorex™ NH; elution solvent: heptane-ethyl acetate system)
  11. customagain purified with silica gel column chromatography (elution solvent: ethyl acetate-methanol system)
  12. custompurified by LC-MS
  13. concentrationAfter concentrating the target fraction, ethyl acetate
  14. additiona saturated sodium bicarbonate solution were added to the residue
  15. customthe organic layer was separated
  16. washThe organic layer washed with brine
  17. dry with materialdried over anhydrous magnesium sulfate
  18. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a145ceae31d6499a8798085c88d42d8b
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07713993B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes