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1,2-Dimethoxyethane → 1-[(5-Chloroindol-2-yl)sulfonyl]-4-[[5-(pyridin-4-yl)pyrimidin-2-yl]carbonyl]piperazine

HRID 352914
Notes
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Reaction equation

HRID 352914 reaction equation
C(COC)OC.Br[C:8]1[CH:9]=[N:10][C:11]([C:14]([N:16]2[CH2:21][CH2:20][N:19]([S:22]([C:25]3[NH:26][C:27]4[C:32]([CH:33]=3)=[CH:31][C:30]([Cl:34])=[CH:29][CH:28]=4)(=[O:24])=[O:23])[CH2:18][CH2:17]2)=[O:15])=[N:12][CH:13]=1.[N:35]1[CH:40]=[CH:39][C:38](OB(O)O)=[CH:37][CH:36]=1.[F-].[Cs+]>[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.CO>[Cl:34][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[NH:26][C:25]([S:22]([N:19]1[CH2:20][CH2:21][N:16]([C:14]([C:11]3[N:10]=[CH:9][C:8]([C:38]4[CH:39]=[CH:40][N:35]=[CH:36][CH:37]=4)=[CH:13][N:12]=3)=[O:15])[CH2:17][CH2:18]1)(=[O:24])=[O:23])=[CH:33]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 25953Cesium fluorideHCID 218058124-Pyridylboric acidHCID 227095721-[(5-Bromopyrimidin-2-yl)carbonyl]-4-[(5-chloroindol-2-yl)sulfonyl]piperazine

Product 1

HCID 53268791-[(5-Chloroindol-2-yl)sulfonyl]-4-[[5-(pyridin-4-yl)pyrimidin-2-yl]carbonyl]piperazineYield 40%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolvent

Procedure

In a mixed solvent of dimethoxyethane (10 ml) and methanol (10 ml), 1-[(5-bromopyrimidin-2-yl)carbonyl]-4-[(5-chloroindol-2-yl)sulfonyl]piperazine (485 mg) and 4-pyridylboric acid (197 mg) were suspended at room temperature, followed by the successive addition of tetrakis(triphenylphosphine) palladium (0) (116 mg) and cesium fluoride (1.00 g). The resulting mixture was heated under reflux for 1 week. After the reaction mixture was cooled to room temperature, it was concentrated under reduced pressure. Dichloromethane and water were added to the concentrate to separate the organic layer. The organic layer thus obtained was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (2% methanol—dichloromethane). The pale yellow crystals precipitated in ethanol were collected by filtration and dissolved in dichloromethane. To the resulting solution, 1N aqueous hydrochloride in ethanol was added and the resulting mixture was distilled under reduced pressure to remove the solvent. The yellow crystals precipitated in ethyl acetate were collected by filtration and dried, whereby the title compound (40%) was obtained.

Workup

  1. customwere suspended at room temperature
  2. temperatureThe resulting mixture was heated
  3. temperatureunder reflux for 1 week
  4. concentrationit was concentrated under reduced pressure
  5. additionDichloromethane and water were added to the
  6. concentrationconcentrate
  7. customto separate the organic layer
  8. customThe organic layer thus obtained
  9. dry with materialwas dried over anhydrous sodium sulfate
  10. customThe residue obtained
  11. distillationby distilling off the solvent under reduced pressure
  12. customwas purified by chromatography on a silica gel column (2% methanol—dichloromethane)
  13. customThe pale yellow crystals precipitated in ethanol
  14. filtrationwere collected by filtration
  15. dissolutiondissolved in dichloromethane
  16. additionTo the resulting solution, 1N aqueous hydrochloride in ethanol was added
  17. distillationthe resulting mixture was distilled under reduced pressure
  18. customto remove the solvent
  19. customThe yellow crystals precipitated in ethyl acetate
  20. filtrationwere collected by filtration
  21. customdried

Sources & evidence

ORD record
ord-517d46abee494e63ab9b657d7a796e18
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06747023B1

Reaction notes

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