Potassium Carbonate → HCID 59773474、化合物

HRID 2114273ノート

反応式

HRID 2114273 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 59773474HCID 59773474、化合物

試薬・触媒・溶媒 2

HCID 311Citric Acid溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e8a31bada58841b4bbb0df52f1feb51f
出典データセット
uspto-grants-2008_10
特許番号
US07432379B2

反応ノート

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