Potassium Carbonate → HCID 59773474, 화합물

HRID 2114273노트

반응식

HRID 2114273 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 59773474HCID 59773474, 화합물

시약·촉매·용매 2

HCID 311Citric Acid용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e8a31bada58841b4bbb0df52f1feb51f
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432379B2

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