Ethyl 6-bromo-1-benzofuran-3-carboxylate → HCID 67517858, compound

HRID 2173347Notes

Reaction equation

HRID 2173347 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]2[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][O:8][C:4]=2[CH:3]=1.[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.[K]>CC(N(C)C)=O.[Cu]I>[O:21]=[C:19]1[C:18]2[C:17](=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16](=[O:26])[N:20]1[C:2]1[CH:15]=[CH:14][C:5]2[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 19371000Ethyl 6-bromo-1-benzofuran-3-carboxylateHCID 24194345Phthalimide potassium salt

Product 1

HCID 67517858HCID 67517858, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

A solution of ethyl 6-bromo-1-benzofuran-3-carboxylate (14.90 g, 55.4 mmol) in 200 mL of DMA was added potassium phthalimide (10.3 g, 55.4 mmol) and CuI (10.6 g, 55.4 mmol) and the mixture was stirred at 150° C. under nitrogen atmosphere overnight. The reaction mixture was concentrated under vacuum, and the residue was dissolved in DCM, filtered through Celite®. The filtration was concentrated and purified with silica gel column chromatograph to give ethyl 6-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-1-benzofuran-3-carboxylate.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionthe residue was dissolved in DCM
  3. filtrationfiltered through Celite®
  4. filtrationThe filtration
  5. concentrationwas concentrated
  6. custompurified with silica gel column chromatograph

Sources & evidence

ORD record
ord-4f33c8213622445386f2f2d185cd4427
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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