Water → HCID 86630992, compound

HRID 2090719Notes

Reaction equation

HRID 2090719 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[CH:9]=1.[I:15]N1C(=O)CCC1=O.O>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:12][CH:11]=[C:10]([CH:13]=[O:14])[C:9]=1[I:15]

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 469085935-(2-Fluorophenyl)-1H-pyrrole-3-carboxaldehyde

Product 1

HCID 86630992HCID 86630992, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(2-Fluorophenyl)-1H-pyrrole-3-carbaldehyde (2.0 g) was dissolved in N,N-dimethylformamide (60 mL), N-iodosuccinimide (2.38 g) was added and the mixture was stirred at for 12 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed successively with a saturated aqueous sodium hydrogencarbonate solution, a 3% aqueous potassium hydrogensulfate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:3→1:1) to give the title compound as a pale-brown powder (yield 450 mg, 14%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed successively with a saturated aqueous sodium hydrogencarbonate solution
  3. dry with materiala 3% aqueous potassium hydrogensulfate solution and saturated brine, dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=7:3→1:1)

Sources & evidence

ORD record
ord-525281fe870c478ca5dfe400793a6b01
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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