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Sodium hydride → 5-(2-chloropyridin-3-yl)-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrole-3-carbaldehyde

HRID 1426666
Notes
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Reaction equation

HRID 1426666 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[CH3:32][C:33]1[N:38]=[CH:37][C:36]([S:39](Cl)(=[O:41])=[O:40])=[CH:35][CH:34]=1>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[C:7]([C:8]2[N:12]([S:39]([C:36]3[CH:37]=[N:38][C:33]([CH3:32])=[CH:34][CH:35]=3)(=[O:41])=[O:40])[CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 223987146-Methylpyridine-3-sulfonyl chlorideHCID 866239825-(2-chloropyridin-3-yl)-1H-pyrrole-3-carbaldehyde

Product 1

HCID 866239835-(2-chloropyridin-3-yl)-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrole-3-carbaldehydeYield 25%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-(2-chloropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (207 mg) in tetrahydrofuran (20 mL) was added sodium hydride (60% in oil, 100 mg) at room temperature and the mixture was stirred for 10 min. 15-Crown-5 (552 mg) was added dropwise, and the mixture was stirred for 5 min. 6-Methylpyridine-3-sulfonyl chloride (250 mg) was added, and the mixture was further stirred for 1 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=3:7→1:4) to give the title compound as a colorless oil (yield 90 mg, 25%).

Workup

  1. stirringthe mixture was stirred for 5 min
  2. stirringthe mixture was further stirred for 1 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=3:7→1:4)

Sources & evidence

ORD record
ord-b0949d2d2bc14c1a83f85c6006316aaa
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08933105B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes