Sodium hydride → HCID 86630977, compound

HRID 1962576Notes

Reaction equation

HRID 1962576 reaction equation
[H-].[Na+].[CH:3]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[NH:19][CH:18]=[C:17]([CH:20]=[O:21])[CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([S:28](Cl)(=[O:30])=[O:29])[CH:23]=1>O1CCCC1>[CH:3]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[N:19]([S:28]([C:24]4[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=4)(=[O:30])=[O:29])[CH:18]=[C:17]([CH:20]=[O:21])[CH:16]=3)=[CH:11][CH:10]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3164136Pyridine-3-sulfonyl chlorideHCID 86630972HCID 86630972, compound

Product 1

HCID 86630977HCID 86630977, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil, 68 mg) was added to a solution of 5-(4-cyclohexylphenyl)-1H-pyrrole-3-carbaldehyde (0.17 g) in tetrahydrofuran (12 mL) at room temperature. The mixture was stirred for 20 min, 3-pyridinesulfonyl chloride (0.19 g) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into ice water, 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=3:2→2:1) to give the title compound as crystals (yield 0.26 g, 97%).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=3:2→2:1)

Sources & evidence

ORD record
ord-915ed77b5d2b4e8980d5becb81491d41
Source dataset
uspto-grants-2013_04
Patent number
US08415368B2

Reaction notes

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