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

HRID 1426670Notes

Reaction equation

HRID 1426670 reaction equation
[H-].[Na+].[Br:3][C:4]1[NH:8][CH:7]=[C:6]([CH2:9][N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=1.C1OCCOCCOCCOCCOC1.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([S:40](Cl)(=[O:42])=[O:41])[CH:35]=1>O1CCCC1.O>[C:13]([O:12][C:11](=[O:17])[N:10]([CH2:9][C:6]1[CH:5]=[C:4]([Br:3])[N:8]([S:40]([C:36]2[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=2)(=[O:42])=[O:41])[CH:7]=1)[CH3:18])([CH3:14])([CH3:15])[CH3:16]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 3164136Pyridine-3-sulfonyl chlorideHCID 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 68.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 7.4 g) in tetrahydrofuran (300 mL) was added a solution of tert-butyl [(5-bromo-1H-pyrrol-3-yl)methyl]methylcarbamate (44.5 g) in tetrahydrofuran (60 mL) at 0° C., and 15-crown-5 (40.7 g) and pyridine-3-sulfonyl chloride (30.1 g) were added at the same temperature. The mixture was stirred at room temperature for 30 min, water was added and the mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with a mixed solvent of diisopropyl ether-hexane=1:1 to give the title compound as colorless crystals (yield 45.2 g, 68%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with a mixed solvent of diisopropyl ether-hexane=1:1

Sources & evidence

ORD record
ord-c8767b0e778848c18c92b5cec2839a8d
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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