Sodium hydride → 3-{[2-(2-chloropyridin-3-yl)-4-formyl-1H-pyrrol-1-yl]sulfonyl}benzonitrile

HRID 1426726Notes

Reaction equation

HRID 1426726 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+].[C:17]([C:19]1[CH:20]=[C:21]([S:25](Cl)(=[O:27])=[O:26])[CH:22]=[CH:23][CH:24]=1)#[N:18]>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[C:7]([C:8]2[N:12]([S:25]([C:21]3[CH:20]=[C:19]([CH:24]=[CH:23][CH:22]=3)[C:17]#[N:18])(=[O:27])=[O:26])[CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 28013603-Cyanobenzene-1-sulfonyl chlorideHCID 866239825-(2-chloropyridin-3-yl)-1H-pyrrole-3-carbaldehyde

Product 1

HCID 866239983-{[2-(2-chloropyridin-3-yl)-4-formyl-1H-pyrrol-1-yl]sulfonyl}benzonitrileYield 76%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-(2-chloropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (110 mg) in tetrahydrofuran (11 mL) was added sodium hydride (60% in oil, 64 mg) at room temperature and the mixture was stirred for 10 min. 3-Cyanobenzenesulfonyl chloride (215 mg) was added and the mixture was further stirred for 15 min. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The obtained extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from diethyl ether to give the title compound as colorless crystals (yield 150 mg, 76%).

Workup

  1. stirringthe mixture was further stirred for 15 min
  2. extractionextracted with ethyl acetate
  3. extractionThe obtained extract
  4. washwas washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-2fb299da3c0f4b52a5ac489ccbebded6
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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