Sodium hydride → HCID 67396861, compound

HRID 1426774Notes

Reaction equation

HRID 1426774 reaction equation
[H-].[Na+].[C:3]([C:5]1[C:10]([C:11]2[NH:15][CH:14]=[C:13]([CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:12]=2)=[CH:9][CH:8]=[CH:7][N:6]=1)#[N:4].[CH3:26][O:27][C:28]1[N:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1>O1CCCC1.C1OCCOCCOCCOCCOC1>[C:3]([C:5]1[C:10]([C:11]2[N:15]([S:34]([C:31]3[CH:32]=[N:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=3)(=[O:35])=[O:36])[CH:14]=[C:13]([CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])[CH:12]=2)=[CH:9][CH:8]=[CH:7][N:6]=1)#[N:4]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 223447096-Methoxypyridine-3-sulfonyl chlorideHCID 67397275HCID 67397275, compound

Product 1

HCID 67396861HCID 67396861, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 3633615-Crown-5Solvent

Procedure

To a suspension of sodium hydride (60% in oil, 26 mg) in tetrahydrofuran (4 mL) were added dropwise a solution of tert-butyl {[5-(2-cyanopyridin-3-yl)-1H-pyrrol-3-yl]methyl}methylcarbamate (156 mg) in tetrahydrofuran (2 mL), 15-crown-5 (0.13 mL) and 6-methoxypyridine-3-sulfonyl chloride (135 mg) under ice-cooling, and the mixture was stirred for 30 min. The reaction mixture was diluted with ice water, and extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer 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=9:1→2:3) to give the title compound as a pale-yellow oil (yield 235 mg, 97%).

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. extractionThe separated aqueous layer was extracted again with ethyl acetate
  4. washThe combined organic layer 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=9:1→2:3)

Sources & evidence

ORD record
ord-d95b8556309c4f018f3e63dd5c9b98d3
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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