Sodium hydride → 4-chloro-5-(2-fluoropyridin-3-yl)-1-{[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrole-3-carbaldehyde

HRID 1426662Notes

Reaction equation

HRID 1426662 reaction equation
[Cl:1][C:2]1[C:3]([CH:14]=[O:15])=[CH:4][NH:5][C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[CH3:33][S:34]([C:37]1[CH:38]=[C:39]([S:43](Cl)(=[O:45])=[O:44])[CH:40]=[CH:41][CH:42]=1)(=[O:36])=[O:35]>O1CCCC1.C(=O)([O-])O.[Na+]>[Cl:1][C:2]1[C:3]([CH:14]=[O:15])=[CH:4][N:5]([S:43]([C:39]2[CH:40]=[CH:41][CH:42]=[C:37]([S:34]([CH3:33])(=[O:36])=[O:35])[CH:38]=2)(=[O:45])=[O:44])[C:6]=1[C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 2203303-(Methylsulfonyl)benzenesulfonyl chlorideHCID 866239794-chloro-5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde

Product 1

HCID 866239804-chloro-5-(2-fluoropyridin-3-yl)-1-{[3-(methylsulfonyl)phenyl]sulfonyl}-1H-pyrrole-3-carbaldehydeYield 57%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 4-chloro-5-(2-fluoropyridin-3-yl)-1H-pyrrole-3-carbaldehyde (250 mg) in tetrahydrofuran (25 mL) was added sodium hydride (60% in oil, 89 mg) at room temperature and the mixture was stirred for 5 min. 15-Crown-5 (490 mg) was added dropwise, and the mixture was stirred for 5 min. 3-(Methylsulfonyl)benzenesulfonyl chloride (426 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=1:1) to give the title compound as a pale-yellow oil (yield 280 mg, 57%).

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=1:1)

Sources & evidence

ORD record
ord-3cfd8552602c445cbb30a05a07bdac7c
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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