Chloranil → 6,8-Dimethyl-1-tosylbenzo[cd]indol-5(1H)-one

HRID 2174022Notes

Reaction equation

HRID 2174022 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]=23

Participants

4

Reactant 2

HCID 8371ChloranilHCID 867016201-(5,7-Dimethyl-1-tosyl-1H-indol-4-yl)prop-2-en-1-one

Product 1

HCID 867016216,8-Dimethyl-1-tosylbenzo[cd]indol-5(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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).

Workup

  1. additionwas added
  2. filtrationfiltered
  3. customto remove
  4. customprecipitated salts
  5. customThe AcOH was removed in vacuo
  6. customthe resulting residue was purified
  7. washeluting with heptane:EtOAc 1:1

Sources & evidence

ORD record
ord-1f6cb26a3f724ae9bfda78a02011d587
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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