Sodium hydride → HCID 86623995, compound

HRID 1426707Notes

Reaction equation

HRID 1426707 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([C:10]2[NH:14][CH:13]=[C:12]([CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:11]=2[F:25])=[CH:8][CH:7]=[CH:6][N:5]=1.C1OCCOCCOCCOCCOC1.[N:41]1[CH:46]=[CH:45][CH:44]=[C:43]([S:47](Cl)(=[O:49])=[O:48])[CH:42]=1>O1CCCC1.O>[Cl:3][C:4]1[C:9]([C:10]2[N:14]([S:47]([C:43]3[CH:42]=[N:41][CH:46]=[CH:45][CH:44]=3)(=[O:49])=[O:48])[CH:13]=[C:12]([CH2:15][N:16]([CH3:24])[C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:22])[CH3:20])[C:11]=2[F:25])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 3164136Pyridine-3-sulfonyl chlorideHCID 86623992HCID 86623992, compound

Product 1

HCID 86623995HCID 86623995, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60% in oil, 60 mg) in tetrahydrofuran (5 mL) were added tert-butyl {[5-(2-chloropyridin-3-yl)-4-fluoro-1H-pyrrol-3-yl]methyl}methylcarbamate, 15-crown-5 (330 mg) and pyridine-3-sulfonyl chloride (266 mg) under ice-cooling and the mixture was stirred for 15 min. The reaction mixture was diluted with 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=4:1→1:1) to give the title compound as a pale-yellow oil (yield 465 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=4:1→1:1)

Sources & evidence

ORD record
ord-a2adcb92e4cc4632a1d77a479200d57e
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

Loading…