Sodium hydride → 1-(1,3-benzodioxol-5-ylsulfonyl)-5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde

HRID 1426660Notes

Reaction equation

HRID 1426660 reaction equation
[F: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.[O:32]1[C:36]2[CH:37]=[CH:38][C:39]([S:41](Cl)(=[O:43])=[O:42])=[CH:40][C:35]=2[O:34][CH2:33]1>O1CCCC1.C(=O)([O-])O.[Na+]>[O:32]1[C:36]2[CH:37]=[CH:38][C:39]([S:41]([N:12]3[C:8]([C:7]4[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=4)=[CH:9][C:10]([CH:13]=[O:14])=[CH:11]3)(=[O:42])=[O:43])=[CH:40][C:35]=2[O:34][CH2:33]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 49134011,3-Benzodioxole-5-sulfonyl chlorideHCID 58349828HCID 58349828, compound

Product 1

HCID 866239781-(1,3-benzodioxol-5-ylsulfonyl)-5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehydeYield 64%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (200 mg) in tetrahydrofuran (20 mL) was added sodium hydride (60% in oil, 64 mg) at room temperature and the mixture was stirred for 10 min. 15-Crown-5 (348 mg) was added dropwise, and the mixture was stirred for 5 min. 1,3-Benzodioxole-5-sulfonyl chloride (250 mg) was added, and the mixture was further stirred for 30 min. 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=3:2→2:3) and crystallized from diethyl ether to give the title compound as colorless crystals (yield 250 mg, 64%).

Workup

  1. stirringthe mixture was stirred for 5 min
  2. stirringthe mixture was further stirred for 30 min
  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=3:2→2:3)
  8. customcrystallized from diethyl ether

Sources & evidence

ORD record
ord-9cfbb840c67f4c33a014d6873db66e24
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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