Sodium hydride → HCID 67147558, compound

HRID 490522Notes

Reaction equation

HRID 490522 reaction equation
[H-].[Na+].[N:3]1([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][C:25]=1[O:26][CH3:27])[N:22]([CH3:28])[CH:21]=[C:20]2[C:29]1[N:43]([S:44]([C:47]2[CH:52]=[CH:51][C:50]([CH3:53])=[CH:49][CH:48]=2)(=[O:46])=[O:45])[C:32]2=[N:33][CH:34]=[CH:35][C:36]([CH2:37]OS(C)(=O)=O)=[C:31]2[CH:30]=1>C1COCC1.O.C(OCC)(=O)C>[CH3:15][O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][C:25]=1[O:26][CH3:27])[N:22]([CH3:28])[CH:21]=[C:20]2[C:29]1[N:43]([S:44]([C:47]2[CH:48]=[CH:49][C:50]([CH3:53])=[CH:51][CH:52]=2)(=[O:46])=[O:45])[C:32]2=[N:33][CH:34]=[CH:35][C:36]([CH2:37][N:12]3[CH2:13][CH2:14][CH:9]([N:3]4[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]4)[CH2:10][CH2:11]3)=[C:31]2[CH:30]=1

Participants

7

Reactant 3

HCID 24758Sodium hydrideHCID 786071,4'-BipiperidineHCID 86612141HCID 86612141, compound

Product 1

HCID 67147558HCID 67147558, compoundYield 85.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.003 g of sodium hydride is added to a solution of 0.008 g of 4-piperidinopiperidine in 0.5 cm3 of THF, at a temperature in the region of 20° C. The reaction medium is stirred at room temperature for 20 minutes. 0.04 g of methanesulfonic acid 2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl ester is added. The reaction medium is heated at 60° C. for 3 hours. After cooling, the reaction medium is concentrated under reduced pressure. The residue obtained is taken up in 2 cm3 of water and 3 cm3 of ethyl acetate. After separation of the phases by settling, the organic phase is dried over magnesium sulfate, filtered and then concentrated under reduced pressure. After purification by flash-pack chromatography (SiO2, dichloromethane/methanol 90/10 by volume as eluent), 0.026 g of 1′-[2-(5,6-dimethoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyrid-4-ylmethyl][1,4′]bipiperidyl is obtained, the characteristics of which are as follows:

Workup

  1. temperatureThe reaction medium is heated at 60° C. for 3 hours
  2. temperatureAfter cooling
  3. concentrationthe reaction medium is concentrated under reduced pressure
  4. customThe residue obtained
  5. customAfter separation of the phases
  6. dry with materialthe organic phase is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customAfter purification by flash-pack chromatography (SiO2, dichloromethane/methanol 90/10 by volume as eluent)

Sources & evidence

ORD record
ord-669bf91d54084db996b40a021c32e091
Source dataset
uspto-grants-2009_05
Patent number
US07528147B2

Reaction notes

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