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 490442Notes

Reaction equation

HRID 490442 reaction equation
[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

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 739534-Piperidineethanol2×HCID 67147680HCID 67147680, compound

Product 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]ethanolYield 57%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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:

Workup

  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)]

Sources & evidence

ORD record
ord-ecaa2b8145774eaab6cb37b6f331355c
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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