2-Chloropyridine → 3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-5-(pyridin-2-yloxy)-1H-indole

HRID 1683929ノート

反応式

HRID 1683929 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=1.[NH2:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][CH:29]=[C:28]2[CH:34]1[CH2:39][CH2:38][N:37]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:36][CH2:35]1.[C:47]([O:51][C:52]([N:54]1[CH2:59][CH2:58][C:57]([C:60]2[C:68]3[C:63](=[CH:64][CH:65]=[C:66]([OH:69])[CH:67]=3)[NH:62][CH:61]=2)=[CH:56][CH2:55]1)=[O:53])([CH3:50])([CH3:49])[CH3:48].Cl[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][N:72]=1.C(=O)([O-])O.[Na+]>O1CCCC1.O1CCOCC1>[C:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][C:11]([C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:36]4[CH:35]=[CH:34][CH:39]=[CH:38][N:37]=4)[CH:3]=3)[NH:7][CH:6]=2)=[CH:12][CH2:13]1)=[O:18])([CH3:23])([CH3:22])[CH3:21].[C:43]([O:42][C:40]([N:37]1[CH2:38][CH2:39][CH:34]([C:28]2[C:27]3[C:31](=[CH:32][CH:33]=[C:25]([NH:24][C:55]4[CH:56]=[CH:57][CH:58]=[CH:59][N:54]=4)[CH:26]=3)[NH:30][CH:29]=2)[CH2:35][CH2:36]1)=[O:41])([CH3:46])([CH3:45])[CH3:44].[C:47]([O:51][C:52]([N:54]1[CH2:59][CH2:58][C:57]([C:60]2[C:68]3[C:63](=[CH:64][CH:65]=[C:66]([O:69][C:71]4[CH:76]=[CH:75][CH:74]=[CH:73][N:72]=4)[CH:67]=3)[NH:62][CH:61]=2)=[CH:56][CH2:55]1)=[O:53])([CH3:50])([CH3:48])[CH3:49]

参加物

10

反応物 5

HCID 79772-ChloropyridineHCID 516892Sodium BicarbonateHCID 158394613-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-5-hydroxy-1H-indoleHCID 53986362tert-butyl 4-(5-amino-1H-indol-3-yl)piperidine-1-carboxylateHCID 543263845-amino-3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-1H-indole

生成物 3

HCID 190407253-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-5-(pyridin-2-yloxy)-1H-indoleHCID 190407463-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-5-(pyrid-2-ylamino)-1H-indoleHCID 190407603-(N-t-butoxycarbonylpiperid-4-yl)-5-(pyrid-2-ylamino)-1H-indole

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 5-amino-3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-1H-indole, 5-amino-3-(N-t-butoxycarbonylpiperid-4-yl)-1H-indole, or 3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-5-hydroxy-1H-indole (10.0 mmol) and a base (12.0 mmol, 1.2 eq) in anhydrous tetrahydrofuran or dioxane (35 mL) was added the 2-chloropyridine (11.0 mmol, 1.1 eq). The resulting reaction solution was stirred at reflux or at room temperature under nitrogen for 3-48 hours, depending on substrate and reaction solvent. A saturated solution of sodium hydrogen carbonate (25 mL) was then added to the reaction mixture, and this aqueous mixture was extracted with ethyl acetate (3×25 mL). The organic extracts were combined, dried (Mg SO4), and evaporated under reduced pressure. The extraction residue was column chromatographed using silica gel (approximately 150 g) and elution with the appropriate solvent system to afford the desired 3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-5-(pyrid-2-ylamino)-1H-indole, 3-(N-t-butoxycarbonylpiperid-4-yl)-5-(pyrid-2-ylamino)-1H-indole or 3-(N-t-butoxycarbonyl-1,2,5,6-tetrahydropyrid-4-yl)-5-(pyridin-2-yloxy)-1H-indole.

後処理

  1. customThe resulting reaction solution
  2. customdepending on substrate and reaction solvent
  3. extractionthis aqueous mixture was extracted with ethyl acetate (3×25 mL)
  4. dry with materialdried (Mg SO4)
  5. customevaporated under reduced pressure
  6. customchromatographed
  7. washsilica gel (approximately 150 g) and elution with the appropriate solvent system

出典と根拠

ORDレコード
ord-f3e79bd8c22b4d3b848b337eb36962ef
出典データセット
uspto-grants-1997_06
特許番号
US05639752

反応ノート

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