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