Trimethylsilyl iodide → HCID 67209859, compound

HRID 402502Notes

Reaction equation

HRID 402502 reaction equation
C[O:2][C:3]1[N:8]=[C:7]2[N:9]([CH3:18])[CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]2=[C:5]([C:19]([F:22])([F:21])[F:20])[CH:4]=1.C[Si](I)(C)C>CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl>[CH3:18][N:9]1[C:7]2[NH:8][C:3](=[O:2])[CH:4]=[C:5]([C:19]([F:21])([F:20])[F:22])[C:6]=2[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10]1

Participants

5

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 67209277HCID 67209277, compound

Product 1

HCID 67209859HCID 67209859, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 6-Methoxy-1-methyl-3-phenyl-4-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine (70 mg, 0.23 mmol), trimethylsilyl iodide (686 mg, 3.43 mmol) and DMAP (3 mg, 0.01 mmol) in chloroform (3 ml) was heated at reflux for 3 days. The reaction mixture was concentrated under reduced pressure. To the mixture water was added and the solution was extracted with EtOAc. The organic layer was washed with water, saturated aqueous sodium bisulfite solution and brine, filtered and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure. The crude product was purified by flash column chromatography (20% EtOAc in hexane) to yield the title compound (43 mg, 64%). [LCMS RtC=0.45 min; [M+H]+=292.8]

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 days
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. additionTo the mixture water was added
  5. extractionthe solution was extracted with EtOAc
  6. washThe organic layer was washed with water, saturated aqueous sodium bisulfite solution and brine
  7. filtrationfiltered
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationThe organic layer was concentrated under reduced pressure
  10. customThe crude product was purified by flash column chromatography (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-75159965d6ee4c13a6360b8aa401b5e6
Source dataset
uspto-grants-2014_06
Patent number
US08742106B2

Reaction notes

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