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

HRID 1683929노트

반응식

HRID 1683929 반응식
[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]

참가 물질

10

반응물 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

생성물 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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f3e79bd8c22b4d3b848b337eb36962ef
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639752

반응 노트

불러오는 중…