Sodium hydride → HCID 86620761, compound

HRID 554333Notes

Reaction equation

HRID 554333 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:11][CH:10]=[C:9]([CH:12]=[O:13])[CH:8]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[F:31][C:32]1[CH:33]=[C:34]([S:39](Cl)(=[O:41])=[O:40])[CH:35]=[CH:36][C:37]=1[F:38]>O1CCCC1.[Cl-].[Na+].O>[F:31][C:32]1[CH:33]=[C:34]([S:39]([N:11]2[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:8][C:9]([CH:12]=[O:13])=[CH:10]2)(=[O:40])=[O:41])[CH:35]=[CH:36][C:37]=1[F:38]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 27369133,4-Difluorobenzene-1-sulfonyl chlorideHCID 86232757HCID 86232757, compound

Product 1

HCID 86620761HCID 86620761, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution (16 mL) of 5-(pyridin-2-yl)-1H-pyrrole-3-carbaldehyde (80 mg) in tetrahydrofuran was added sodium hydride (60% in oil, 56 mg) at room temperature and the mixture was stirred for 30 min. 15-Crown-5 (307 mg) was added dropwise and the mixture was stirred for 30 min, 3,4-difluorobenzenesulfonyl chloride (198 mg) was added, and the mixture was further stirred for 1 hr. Saturated brine was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract 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), and crystallized from diisopropyl ether to give the title compound as colorless crystals (yield 114 mg, 70%).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. stirringthe mixture was further stirred for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract 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)
  8. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-ecbc28cab98149a99febc65049c07bca
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

Loading…