Sodium hydride → HCID 67398445, compound

HRID 1426749Notes

Reaction equation

HRID 1426749 reaction equation
[F:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[O:40]1[C:44]([C:45]2[S:49][C:48]([S:50](Cl)(=[O:52])=[O:51])=[CH:47][CH:46]=2)=[CH:43][CH:42]=[N:41]1>O1CCCC1.C(=O)([O-])O.[Na+]>[F:1][C:2]1[C:7]([C:8]2[N:12]([S:50]([C:48]3[S:49][C:45]([C:44]4[O:40][N:41]=[CH:42][CH:43]=4)=[CH:46][CH:47]=3)(=[O:51])=[O:52])[CH:11]=[C:10]([CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 27953305-isoxazol-5-ylthiophene-2-sulfonyl chlorideHCID 67396538HCID 67396538, compound

Product 1

HCID 67398445HCID 67398445, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of tert-butyl {[5-(2-fluoropyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate (200 mg) in tetrahydrofuran (10 mL) was added sodium hydride (60% in oil, 53 mg) under ice-cooling, and the mixture was stirred for 20 min. After stirring, 15-crown-5 (290 mg) was added. 5-Isoxazol-5-ylthiophene-2-sulfonyl chloride (246 mg) was added and the mixture was further stirred under ice-cooling 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 colorless oil (yield 80 mg, 24%).

Workup

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

Sources & evidence

ORD record
ord-5e6f0ab99fa24c7d90f43cd3440590f3
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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