Iodobenzene → HCID 21714953, compound

HRID 650311Notes

Reaction equation

HRID 650311 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[CH2:12][CH:11]=[CH:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC([O-])=O.CC([O-])=O.[Pd+2].C(N(CC)CC)C>[C:17]1([C:11]2[CH2:12][C:13]3[C:9]([CH:10]=2)=[N:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:15][CH:14]=3)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 11575IodobenzeneHCID 21714966HCID 21714966, compound

Product 1

HCID 21714953HCID 21714953, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

20 ml of triethylamine, 3.86 g (20 mmol) of 5-phenyl-4-aza-indene, 4.08 g (20 mmol) of iodo-benzene and 0.134 g (0.6 mmol) of Pd(OAc)2 were stirred under reflux for 10 h. After that all triethylamine was removed under reduced pressure. The residue was treated with the mixture 50 ml of dichloromethane and 50 ml of water. Organic layer was separated, washed twice with water, filtered and dried over Na2SO4. Dichloromethane was removed and the residue was recrystallized from 20 ml of EtOH. The yield of product was 23%.

Workup

  1. temperatureunder reflux for 10 h
  2. customAfter that all triethylamine was removed under reduced pressure
  3. additionThe residue was treated with the mixture 50 ml of dichloromethane and 50 ml of water
  4. customOrganic layer was separated
  5. washwashed twice with water
  6. filtrationfiltered
  7. dry with materialdried over Na2SO4
  8. customDichloromethane was removed
  9. customthe residue was recrystallized from 20 ml of EtOH

Sources & evidence

ORD record
ord-92278580a92a4b5cafa8006be51bb275
Source dataset
uspto-grants-2001_08
Patent number
US06271411B1

Reaction notes

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