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Sodium hydride → tert-butyl({5-bromo-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamate

HRID 1012518
Notes
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Reaction equation

HRID 1012518 reaction equation
[C:1]([O:5][C:6](=[O:16])[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([Br:15])[NH:12][CH:11]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C1OCCOCCOCCOCCOC1.[CH3:34][C:35]1[N:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>O1CCCC1.O>[C:1]([O:5][C:6](=[O:16])[N:7]([CH2:9][C:10]1[CH:14]=[C:13]([Br:15])[N:12]([S:41]([C:38]2[CH:39]=[N:40][C:35]([CH3:34])=[CH:36][CH:37]=2)(=[O:43])=[O:42])[CH:11]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 223987146-Methylpyridine-3-sulfonyl chlorideHCID 57522147tert-Butyl ((5-bromo-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Product 1

HCID 66974470tert-butyl({5-bromo-1-[(6-methylpyridin-3-yl)sulfonyl]-1H-pyrrol-3-yl}methyl)methylcarbamateYield 79%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl[(5-bromo-1H-pyrrol-3-yl)methyl]methylcarbamate (207 mg) in tetrahydrofuran (30 mL) was added sodium hydride (60% in oil, 31 mg) at 0° C., and the mixture was stirred at the same temperature for 10 min. A solution (3 mL) of 15-crown-5 (0.16 mL) and 6-methylpyridin-3-ylsulfonyl chloride (117 mg) in tetrahydrofuran was added at the same temperature. After stirring at room temperature for 30 min, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a 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=4:1) to give the title compound as a brown oil (yield 213 mg, 79%).

Workup

  1. stirringAfter stirring at room temperature for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=4:1)

Sources & evidence

ORD record
ord-1cd83f3f5dbd4c9a8c373c2dc31ea413
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977488B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes