3-(4-Chlorophenyl)-4-(methylsulfanyl)-1h-indole-2-carboxylic acid → 3-(4-Chlorophenyl)-1h-indol-4-yl methyl sulfide

HRID 857320노트

반응식

HRID 857320 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[S:17][CH3:18])[NH:10][C:9]=2C(O)=O)=[CH:4][CH:3]=1>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH3:18][S:17][C:15]1[C:16]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[CH:9][NH:10][C:11]=2[CH:12]=[CH:13][CH:14]=1

참가 물질

4

반응물 1

HCID 218674693-(4-Chlorophenyl)-4-(methylsulfanyl)-1h-indole-2-carboxylic acid

생성물 1

HCID 218674683-(4-Chlorophenyl)-1h-indol-4-yl methyl sulfide수율 62.2%

시약·촉매·용매 2

HCID 23978Copper촉매HCID 7047Quinoline용매

실험 절차

To a solution of 1.4 g of the acid of Step 5 in quinoline (10 mL) was added 100 mg of copper powder. The reaction mixture was heated to reflux and stirred for 2 hours. The copper powder was removed by filtration and 6N HCl was added to the filtrate. The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 10% EtOAc in Hexanes to provide 750 mg of the title compound as an orange solid foam.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customThe copper powder was removed by filtration and 6N HCl
  4. additionwas added to the filtrate
  5. extractionThe aqueous layer was extracted with EtOAc
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography
  9. washeluted with 10% EtOAc in Hexanes

출처 및 근거

ORD 기록
ord-4b325d8d83d14537ac7866120097b3d6
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07144913B2

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