1,8-Diazabicyclo(5.4.0)undec-7-ene → (E)-2-{2-[2-(1H-indazol-3-yl)vinyl]phenoxy}ethanol

HRID 1821342Notes

Reaction equation

HRID 1821342 reaction equation
[Br-].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[N:3]1.C1CCN2C(=NCCC2)CC1.[OH:42][CH2:43][CH2:44][O:45][C:46]1[CH:53]=[CH:52][CH:51]=[CH:50][C:47]=1[CH:48]=O>CO>[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](/[CH:11]=[CH:48]/[C:47]2[CH:50]=[CH:51][CH:52]=[CH:53][C:46]=2[O:45][CH2:44][CH2:43][OH:42])=[N:3]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 939892-(2-Hydroxyethoxy)benzaldehydeHCID 178419401HCID 178419401, compound

Product 1

HCID 69004426(E)-2-{2-[2-(1H-indazol-3-yl)vinyl]phenoxy}ethanolYield 40.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.10 g, 0.21 mmol) in methanol (0.60 mL), DBU (0.079 mL, 0.53 mmol) was added and 2-(2-hydroxyethoxybenzaldehyde (0.039 g, 0.23 mmol) was further added, followed by stirring at room temperature for 2.0 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5). The obtained compound was added with 2.0 mol/L hydrogen chloride-ethyl acetate solution (2.0 mL) and washed, then the precipitated solid was collected by filtration. The obtained solid was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate solution to separate the mixture into organic layer and aqueous layer. The organic layer was concentrated under reduced pressure and the residue was dried under reduced pressure to obtain Compound 134 (0.024 g, 9%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5)
  3. additionThe obtained compound was added with 2.0 mol/L hydrogen chloride-ethyl acetate solution (2.0 mL)
  4. washwashed
  5. filtrationthe precipitated solid was collected by filtration
  6. additionThe obtained solid was added with ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  7. customto separate the mixture into organic layer and aqueous layer
  8. concentrationThe organic layer was concentrated under reduced pressure
  9. customthe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-fb90c19993d8494799da6996c5e5984e
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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