HCID 71278662, compound → HCID 178498961, compound

HRID 1749910Notes

Reaction equation

HRID 1749910 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[C:7](=[O:10])[CH2:8][O:9][C:5]=2[C:4]=1[C:13]([O:15][CH3:16])=[O:14].[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH:26]=O)=[N:18]1>CO.N1CCCCC1>[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19](/[CH:26]=[C:8]2\[O:9][C:5]3[C:4]([C:13]([O:15][CH3:16])=[O:14])=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:6]=3[C:7]\2=[O:10])=[N:18]1

Participants

5

Reactant 2

HCID 71278662HCID 71278662, compoundHCID 178520025HCID 178520025, compound

Product 1

HCID 178498961HCID 178498961, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl 6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-carboxylate (0.070 g, 0.32 mmol) in methanol (5.0 mL) was added with 1H-indazole-3-carboxaldehyde (0.046 g, 0.32 mmol). Then, the mixture was added with 7 drops of piperidine, then the mixture was stirred at room temperature for 2 hours, and the solid formed was collected by filtration to obtain the objective substance. Further, the filtrate was concentrated, and then the residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (97:3→90:10)) to obtain the objective substance. Two portions of the objective substance was combined to obtain 0.090 g (80%) of methyl (Z)-2-[(1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-carboxylate.

Workup

  1. customthe solid formed
  2. filtrationwas collected by filtration
  3. customto obtain the objective substance
  4. concentrationFurther, the filtrate was concentrated
  5. washthe residue was subjected to silica gel column chromatography (eluted with chloroform/methanol (97:3→90:10))
  6. customto obtain the objective substance

Sources & evidence

ORD record
ord-890ba2018ae24504b53b6c6f13d0570f
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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