Chloranil → 6,8-Dimethyl-1-tosylbenzo[cd]indol-5(1H)-one
Reaction equation
[CH3:1][C:2]1[C:3]([C:22](=[O:25])[CH:23]=[CH2:24])=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[N:7]([S:12]([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>CC(O)=O>[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]2[N:7]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:6]=[C:5]3[CH:24]=[CH:23][C:22](=[O:25])[C:3]=1[C:4]=23Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a mixture of 1-(5,7-dimethyl-1-tosyl-1H-indol-4-yl)prop-2-en-1-one (240 mg, 0.679 mmol), PdOAc2 (152 mg, 0.679 mmol) and P-CHLORANIL (167 mg, 0.679 mmol), AcOH (7 mL) was added and the reaction heated to 100° C. for 1.5 h. The reaction was stopped and filtered to remove precipitated salts. The AcOH was removed in vacuo and then the resulting residue was purified using FCC eluting with heptane:EtOAc 1:1 to give the title compound. MS (ESI+) m/z 352.3 (M+H).