5-Methoxy-6-(trifluoromethyl)indoline → HCID 10837468, 화합물

HRID 1603807노트

반응식

HRID 1603807 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:15]3[O:14][CH2:13][CH2:12][C:11]=3[CH:10]=[C:9]([NH:16][C:17](=[O:25])OC3C=CC=CC=3)[CH:8]=2)[CH:2]=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][C:36]=1[C:37]([F:40])([F:39])[F:38])[NH:33][CH2:32][CH2:31]2>CN(C=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[C:15]3[O:14][CH2:13][CH2:12][C:11]=3[CH:10]=[C:9]([NH:16][C:17]([N:33]3[C:34]4[C:30](=[CH:29][C:28]([O:27][CH3:26])=[C:36]([C:37]([F:39])([F:40])[F:38])[CH:35]=4)[CH2:31][CH2:32]3)=[O:25])[CH:8]=2)[CH:2]=1

참가 물질

4

반응물 2

HCID 112067135-Methoxy-6-(trifluoromethyl)indolineHCID 18005145HCID 18005145, 화합물

생성물 1

HCID 10837468HCID 10837468, 화합물수율 26%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Phenyl N-[2,3-dihydro-7-(pyrid-3-yl)benzofuran-5-yl]carbamate (D65) (0.20 g, 0.00060mole) in dry DMF (10 ml) was treated under argon with 5-methoxy-6 trifluoromethyl indoline (D11) (0.13 g, 0.00060 mole) and heated under reflux for 18 hours. The reaction was allowed to cool to ambient temperature and the solvent was removed in vacuo. The residue was dissolved in dichloromethane, washed with deionised water and 10% sodium hydroxide solution, dried (Na2SO4) and evaporated in vacuo. The resulting brown oil was purified by flash column chromatography on silica gel, eluting with 2% methanol/dichloromethane, followed by recrystallisation from ethyl acetate 60-80° petroleum ether to afford the title compound (0.07 g, 26%) as a beige solid.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 18 hours
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed with deionised water and 10% sodium hydroxide solution
  6. dry with materialdried (Na2SO4)
  7. customevaporated in vacuo
  8. customThe resulting brown oil was purified by flash column chromatography on silica gel
  9. washeluting with 2% methanol/dichloromethane
  10. customfollowed by recrystallisation from ethyl acetate 60-80° petroleum ether

출처 및 근거

ORD 기록
ord-5b68f605669e4833aec4f968db261665
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05990133

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