5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1-[(4-pyridyl)methyl]-1H-pyrrole → HCID 22718414, compound

HRID 1582658Notes

Reaction equation

HRID 1582658 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH3:22])=[CH:12][C:11]=2[CH:23]([CH3:25])[CH3:24])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])(=[O:28])C.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Pb+4]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:13]([CH:22]=[O:28])=[CH:12][C:11]=2[CH:23]([CH3:25])[CH3:24])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 227183995-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1-[(4-pyridyl)methyl]-1H-pyrroleHCID 178418268HCID 178418268, compound3×

Product 1

HCID 22718414HCID 22718414, compoundYield 13.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 160 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1-[(4-pyridyl)methyl]-1H-pyrrole in 3 ml of acetic acid was added 200 mg of lead tetraacetate over 30 min. After stirring for 2 h at room temperature a further 100 mg of lead tetraacetate was added and the mixture stirred for 18 h. After this time a further 100 mg of lead tetraacetate was added and the mixture stirred for 18 h. The reaction was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using petrol/ethyl acetate (1:4 then 1:2) then ethyl acetate for the elution to give 23 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-[(4-pyridyl)methyl]-1H-pyrrole-2-carbaldehyde, mass spectrum (ESI) m/z 405 [M+H]+, as a brown oil and 51 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-[(4-pyridyl)methyl]-1H-pyrrole-2-acylmethanol as an impure yellow foaming oil, Mass spectrum (ESI) m/z 447 [M+H]+.

Workup

  1. additionwas added
  2. stirringthe mixture stirred for 18 h
  3. customThe reaction was quenched with saturated sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica gel
  9. wash1:2) then ethyl acetate for the elution

Sources & evidence

ORD record
ord-5d4b193b2db3405dbca4b9238859ae85
Source dataset
uspto-grants-2004_05
Patent number
US06737429B2

Reaction notes

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