1,8-Diazabicyclo(5.4.0)undec-7-ene → (E)-3-[2-(2-methylsulfanylphenyl)vinyl]-1H-indazole

HRID 1821350Notes

Reaction equation

HRID 1821350 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.[CH3:42][S:43][C:44]1[CH:51]=[CH:50][CH:49]=[CH:48][C:45]=1[CH:46]=O>CO>[CH3:42][S:43][C:44]1[CH:51]=[CH:50][CH:49]=[CH:48][C:45]=1/[CH:46]=[CH:11]/[C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:2][N:3]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2864432-(Methylthio)benzaldehydeHCID 178419401HCID 178419401, compound

Product 1

HCID 69001353(E)-3-[2-(2-methylsulfanylphenyl)vinyl]-1H-indazoleYield 28.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (1H-indazol-3-ylmethyl)triphenylphosphonium bromide (0.10 g, 0.21 mmol) in methanol (0.60 mL) was added with DBU (0.047 mL, 0.32 mmol) and 2-methylsulfanylbenzaldehyde (0.035 g, 0.23 mmol) obtained in Step 2 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 washed with hydrogen chloride-ethyl acetate solution and the precipitated solid was filtered. Then the solid was added with saturated aqueous sodium hydrogencarbonate solution and ethyl acetate to separate the mixture into organic layer and aqueous layer. The organic layer was concentrated under reduced pressure and the residue was washed with ethyl acetate/hexane (2/1, 1.0 mL) to obtain Compound 146 (0.016 g, 28%).

Workup

  1. additionwas further added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 95/5)
  4. washThe obtained compound was washed with hydrogen chloride-ethyl acetate solution
  5. filtrationthe precipitated solid was filtered
  6. additionThen the solid was added with saturated aqueous sodium hydrogencarbonate solution and ethyl acetate
  7. customto separate the mixture into organic layer and aqueous layer
  8. concentrationThe organic layer was concentrated under reduced pressure
  9. washthe residue was washed with ethyl acetate/hexane (2/1, 1.0 mL)

Sources & evidence

ORD record
ord-a60b3e257aab4a8eb5befc131dd49330
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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