Sodium hydride → HCID 66924958, compound

HRID 554263Notes

Reaction equation

HRID 554263 reaction equation
[Br:1][C:2]1[NH:6][C:5]([CH3:7])=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.Cl.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([S:37](Cl)(=[O:39])=[O:38])[CH:32]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[Br:1][C:2]1[N:6]([S:37]([C:33]2[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=2)(=[O:39])=[O:38])[C:5]([CH3:7])=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=1

Participants

7

Reactant 5

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 516892Sodium BicarbonateHCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideHCID 52987784HCID 52987784, compound

Product 1

HCID 66924958HCID 66924958, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-bromo-2-methyl-1H-pyrrole-3-carboxylate (2.26 g) was dissolved in tetrahydrofuran (100 mL), sodium hydride (60% in oil, 1.16 g) was added and the mixture was stirred at room temperature for 15 min. 15-Crown-5 (5.90 mL) was added and the mixture was further stirred at the same temperature for 15 min, and 3-pyridinesulfonyl chloride hydrochloride (3.13 g) was added. The reaction mixture was stirred at room temperature for 1 hr, saturated aqueous sodium hydrogencarbonate solution was added, and the mixture was 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=19:1→7:3) to give the title compound as a yellow oil (yield 2.31 g, 64%).

Workup

  1. stirringthe mixture was further stirred at the same temperature for 15 min
  2. stirringThe reaction mixture was stirred at room temperature for 1 hr
  3. extractionthe mixture was extracted 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=19:1→7:3)

Sources & evidence

ORD record
ord-4edc92abb9364c1cb3bc80efc7e0bff7
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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