Potassium Carbonate → HCID 59773474, compound

HRID 2114273Notes

Reaction equation

HRID 2114273 reaction equation
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[SH:12])[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:19][O:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28]Br>CN(C=O)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH3:19][O:20][C:21](=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][S:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[N:2]=[CH:3][CH:4]=[CH:5]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 3082386Quinoline-8-thiol hydrochloride

Product 1

HCID 59773474HCID 59773474, compound

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4.0 eq. of quinoline-8-thiol hydrochloride (39, Aldrich, cat. no. 35,978-5) was dissolved in DMF. To this was added 32.0 eq. of potassium carbonate. The mixture was stirred at room temperature for 20 minutes and 1.0 eq of 2-bromomethyl-benzoic acid methyl ester (40, J. Org. Chem, 2002, 67, 2160) was added. The mixture was stirred at room temperature for a time sufficient enough for reaction completion. The mixture was diluted with 0.1 M citric acid and extracted with EtOAc. The organic layer was washed with brine and dried with Na2SO4, filtered, and concentrated. The product was purified by flash chromatography on silica gel using a mixture of EtOAc-hexanes as eluant to give 41.

Workup

  1. stirringThe mixture was stirred at room temperature for a time sufficient enough for reaction completion
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by flash chromatography on silica gel using
  8. additiona mixture of EtOAc-hexanes as eluant

Sources & evidence

ORD record
ord-e8a31bada58841b4bbb0df52f1feb51f
Source dataset
uspto-grants-2008_10
Patent number
US07432379B2

Reaction notes

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