5-Methoxy-6-(trifluoromethyl)indoline → HCID 10837468、化合物

HRID 989219ノート

反応式

HRID 989219 の反応式
[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

参加物

4

反応物 2

HCID 112067135-Methoxy-6-(trifluoromethyl)indolineHCID 18005145HCID 18005145、化合物

生成物 1

HCID 10837468HCID 10837468、化合物収率 26%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Phenyl N-[2,3-dihydro-7-(pyrid-3-yl)benzofuran-5-yl]carbamate (D65) (0.20 g, 0.00060 mole) 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.

後処理

  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 eluting with 2% methanol/dichloromethane
  9. customfollowed by recrystallisation from ethyl acetate 60.80° petroleum ether

出典と根拠

ORDレコード
ord-56e7dc40820441d6a59207a31ee01d62
出典データセット
uspto-grants-2003_10
特許番号
US06638953B2

反応ノート

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