Quinoline → HCID 89767976, compound

HRID 591479Notes

Reaction equation

HRID 591479 reaction equation
[C:1]([CH2:4][O:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[CH:14][C:9]=2[S:8][C:7]=1C(O)=O)([OH:3])=[O:2].N1C2C(=CC=CC=2)C=CC=1>CCOC(C)=O.[Cu]>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[CH2:16][O:15][C:13]1[CH:12]=[CH:11][C:10]2[C:6]([O:5][CH2:4][C:1]([OH:3])=[O:2])=[CH:7][S:8][C:9]=2[CH:14]=1

Participants

5

Reactant 2

HCID 7047QuinolineHCID 89767889HCID 89767889, compound

Product 1

HCID 89767976HCID 89767976, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
190 °C

Procedure

The mixture of 3-(carboxymethoxy)-6-((2,4-dichlorobenzyl)oxy)-1-benzothiophene-2-carboxylic acid (92.0 mg), copper (13.7 mg) and quinoline (1.5 mL) was heated at 190° C. for 10 min. The mixture was diluted with EtOAc. The mixture was washed successively with 1N HCl and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane), and washed with hexane to give the title compound (63.9 mg).

Workup

  1. washThe mixture was washed successively with 1N HCl and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)
  5. washwashed with hexane

Sources & evidence

ORD record
ord-e64c818d9ae54aedba4f7c17323e502c
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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