Triethylamine → 3,3-Bis-(4-hydroxy-3,5-dimethyl-phenyl)-1-[3-(4-methoxy-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-1,3-dihydro-indol-2-one

HRID 1297800ノート

反応式

HRID 1297800 の反応式
[OH:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2([C:22]3[CH:27]=[C:26]([CH3:28])[C:25]([OH:29])=[C:24]([CH3:30])[CH:23]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]#[N:20])[C:10]2=[O:21])=[CH:4][C:3]=1[CH3:31].[OH:32][N:33]=[C:34](Cl)[C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1.C(N(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(OCC)C.C1COCC1.O.C(OCC)(=O)C>[OH:29][C:25]1[C:26]([CH3:28])=[CH:27][C:22]([C:9]2([C:5]3[CH:4]=[C:3]([CH3:31])[C:2]([OH:1])=[C:7]([CH3:8])[CH:6]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]3[O:32][N:33]=[C:34]([C:35]4[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=4)[N:20]=3)[C:10]2=[O:21])=[CH:23][C:24]=1[CH3:30]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 27633714-Methoxy-N-hydroxybenzenecarboximidoyl chlorideHCID 86597007[3,3-Bis-(4-hydroxy-3,5-dimethyl-phenyl)-2-oxo-2,3-dihydro-indol-1-yl]-acetonitrile

生成物 1

HCID 589147213,3-Bis-(4-hydroxy-3,5-dimethyl-phenyl)-1-[3-(4-methoxy-phenyl)-[1,2,4]oxadiazol-5-ylmethyl]-1,3-dihydro-indol-2-one収率 27.8%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Combine [3,3-Bis-(4-hydroxy-3,5-dimethyl-phenyl)-2-oxo-2,3-dihydro-indol-1-yl]-acetonitrile (0.563 g, 0.878 mmol), N-hydroxy-4-methoxy-benzenecarboximidoyl chloride (1.63 g, 8.78 mmol), and diethyl ether (20 mL). Add a solution of triethylamine (1.35 mL, 9.66 mmol) in diethyl ether (10 mL) over 30 minutes. Stir the reaction at room temperature overnight. Dilute the reaction with ethyl acetate (200 mL) and water (200 mL). Separate the layers, and dry the organic layer with sodium sulfate. Concentrate in vacuo. Chromatograph on silica gel eluting with 20% ethyl acetate in hexanes and concentrate. Dissolve the resulting compound (0.217 g, 0.275 mmol) in THF (2 mL). Add a solution of tetrabutylammonium fluoride (1.0 M) in THF (0.69 mL) and stir the reaction at room temperature for 30 minutes. Quench with 1N aqueous HCl (10 mL), ethyl acetate (50 mL), and water (40 mL). Separate the layers and wash the organic layer with brine (50 mL). Dry the ethyl acetate with sodium sulfate, and concentrate in vacuo. Chromatograph on silica gel eluting with a gradient from 25% to 50% ethyl acetate in hexanes to give 0.137 g of the title compound: mass spectrum (ion spray): m/z=562(M+1); 1H NMR(DMSO-d6): δ8.23 (s, 2H), 7.84-7.82 (m, 2H), 7.28-7.25 (m, 2H), 7.16-7.04 (m, 6H), 6.71 (s, 4H), 5.42 (s, 2H), 3.81 (s, 3H), 2.04 (s, 12H).

後処理

  1. customthe reaction at room temperature overnight
  2. additionDilute
  3. customSeparate the layers
  4. dry with materialdry the organic layer with sodium sulfate
  5. concentrationConcentrate in vacuo
  6. concentrationChromatograph on silica gel eluting with 20% ethyl acetate in hexanes and concentrate
  7. stirringstir
  8. customthe reaction at room temperature for 30 minutes
  9. customQuench with 1N aqueous HCl (10 mL), ethyl acetate (50 mL), and water (40 mL)
  10. customSeparate the layers
  11. washwash the organic layer with brine (50 mL)
  12. dry with materialDry the ethyl acetate with sodium sulfate
  13. concentrationconcentrate in vacuo

出典と根拠

ORDレコード
ord-b06b1398f7e6431da16e216057445028
出典データセット
uspto-grants-2007_07
特許番号
US07250442B2

反応ノート

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