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Potassium Carbonate → 2-[1-(2-{3-[4-chloro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxyindol-1-yl}ethyl)piperidin-4-yl]ethanol

HRID 2426838
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HRID 2426838 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:9]([C:11]3[C:19]4[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]([CH2:24][CH2:25]I)[CH:12]=3)=[CH:10][C:3]=12.C(=O)([O-])[O-].[K+].[K+].[NH:43]1[CH2:48][CH2:47][CH:46]([CH2:49][CH2:50][OH:51])[CH2:45][CH2:44]1>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([S:27]([C:30]3[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=3)(=[O:29])=[O:28])[C:9]([C:11]3[C:19]4[C:14](=[CH:15][C:16]([O:22][CH3:23])=[C:17]([O:20][CH3:21])[CH:18]=4)[N:13]([CH2:24][CH2:25][N:43]4[CH2:48][CH2:47][CH:46]([CH2:49][CH2:50][OH:51])[CH2:45][CH2:44]4)[CH:12]=3)=[CH:10][C:3]=12
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참가 물질

5

반응물 3

HCID 11430Potassium Carbonate2회HCID 739534-Piperidineethanol2회HCID 67147680HCID 67147680, 화합물

생성물 1

HCID 671474712-[1-(2-{3-[4-chloro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxyindol-1-yl}ethyl)piperidin-4-yl]ethanol수율 57%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

A suspension of 0.280 g of 4-chloro-2-[1-(2-iodoethyl)-5,6-dimethoxy-1H-indol-3-yl]-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine, 0.061 g of potassium carbonate and 0.114 g of 2-piperidin-4-ylethanol in 30 ml of acetonitrile is brought to a temperature in the region of 60° C. After heating at this temperature for approximately 5 hours, 0.061 g of potassium carbonate and 0.114 g of 2-piperidin-4-ylethanol are again added and the mixture is agitated at this temperature for approximately 2 hours. After returning to a temperature in the region of 20° C., the mixture is concentrated to dryness under reduced pressure (13 kPa), and then taken up with 50 ml of water and extracted with three times 40 ml of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (13 kPa). The residue is purified by flash chromatography on a silica column [eluent: dichloromethane/methanol (95/5 by volume)]. 0.16 g of 2-[1-(2-{3-[4-chloro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxyindol-1-yl}ethyl)piperidin-4-yl]ethanol is obtained in the form of an oil, the characteristics of which are as follows:

후처리

  1. customis brought to a temperature in the region of 60° C
  2. temperatureAfter heating at this temperature for approximately 5 hours
  3. customAfter returning to a temperature in the region of 20° C.
  4. concentrationthe mixture is concentrated to dryness under reduced pressure (13 kPa)
  5. extractionextracted with three times 40 ml of dichloromethane
  6. dry with materialThe combined organic phases are dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure (13 kPa)
  9. customThe residue is purified by flash chromatography on a silica column [eluent: dichloromethane/methanol (95/5 by volume)]

출처 및 근거

ORD 기록
ord-2e1a05abb60b4eb8ada270ee19143a03
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07968566B2

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