Sodium hydride → tert-Butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamate

HRID 554364Notes

Reaction equation

HRID 554364 reaction equation
[Br:1][C:2]1[NH:6][CH:5]=[C:4]([CH2:7][N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.Cl.[N:35]1[CH:40]=[CH:39][CH:38]=[C:37]([S:41](Cl)(=[O:43])=[O:42])[CH:36]=1>CN(C)C=O.O1CCCC1.O>[Br:1][C:2]1[N:6]([S:41]([C:37]2[CH:36]=[N:35][CH:40]=[CH:39][CH:38]=2)(=[O:43])=[O:42])[CH:5]=[C:4]([CH2:7][N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH:3]=1

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideHCID 57522147tert-Butyl ((5-bromo-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Product 1

HCID 57522258tert-Butyl {[5-bromo-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]methyl}methylcarbamateYield 85.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution (3 mL) of tert-butyl [(5-bromo-1H-pyrrol-3-yl)methyl]methylcarbamate (410 mg) in N,N-dimethylformamide was added to a suspension (10 mL) of sodium hydride (60% in oil, 204 mg) in tetrahydrofuran at 0° C., 15-crown-5 (938 mg) and pyridin-3-ylsulfonyl chloride hydrochloride (456 mg) were added at the same temperature. After stirring at room temperature for 2 hr, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=8:1→3:1) to give the title compound as a pale-yellow powder (yield 522 mg, 85%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=8:1→3:1)

Sources & evidence

ORD record
ord-7139ab2d223d45738fba99fc06801da8
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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