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1,4-Dioxane → 5-(1-tert-butoxycarbonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 513859
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인쇄 미리보기

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HRID 513859 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:5])[CH3:2].[C:26]([O:30][C:31]([N:33]1[CH2:38][CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].P([O-])([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:36]1[CH2:37][CH2:38][N:33]([C:31]([O:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:32])[CH2:34][CH:35]=1)=[CH:10][CH:9]=2)=[O:5])[CH3:2]
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참가 물질

7

반응물 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 135158625-bromo-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

생성물 1

HCID 680056275-(1-tert-butoxycarbonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

5-Bromo-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester (844 mg, 2.0 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (742 mg, 2.4 mmol), potassium phosphate (848 mg, 4.0 mmol), and tetrakis(triphenylphosphine) palladium (116 mg, 0.1 mmol) were placed into a flask. After deaeration, the air was replaced with nitrogen. Anhydrous dioxane (16 ml) and water (4 ml) were added to the flask, and this was stirred at 80° C. for 15 hours. After cooling it to room temperature, the reaction mixture was filtered through Celite, and then washed with ethyl acetate. The filtrate was concentrated, and the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography. Thus, 5-(1-tert-butoxycarbonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester was obtained as a colorless amorphous material (1.0 g, 97.2%).

후처리

  1. temperatureAfter cooling it to room temperature
  2. filtrationthe reaction mixture was filtered through Celite
  3. washwashed with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customthe residue obtained by concentration under reduced pressure
  6. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-b157c636ef984b3b9137e71bbbed3293
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09102692B2

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