Sodium hydride → HCID 67396658, compound

HRID 1426773Notes

Reaction equation

HRID 1426773 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].C1OCCOCCOCCOCCOC1.[C:41]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[S:49](Cl)(=[O:51])=[O:50])#[N:42]>O1CCCC1>[C:41]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[S:49]([N:15]1[C:11]([C:10]2[C:5]([C:3]#[N:4])=[N:6][CH:7]=[CH:8][CH:9]=2)=[CH:12][C:13]([CH2:16][N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[CH:14]1)(=[O:51])=[O:50])#[N:42]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 5223472-Cyanobenzenesulfonyl ChlorideHCID 67397275HCID 67397275, compound

Product 1

HCID 67396658HCID 67396658, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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) solution, 15-crown-5 (0.13 mL) and 2-cyanobenzenesulfonyl chloride (151 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=7:3→ethyl acetate) to give the title compound as a pale-yellow oil (yield 239 mg, 100%).

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=7:3→ethyl acetate)

Sources & evidence

ORD record
ord-8eb6381e20f3439485b34cf3d5a3d0be
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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