N-Iodosuccinimide → HCID 58608105, compound

HRID 2243578Notes

Reaction equation

HRID 2243578 reaction equation
[CH2:1]([N:8]1[CH:13]=[CH:12][C:11](=[O:14])[C:10]2[C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:16]([Si](C)(C)C)[O:17][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:28]N1C(=O)CCC1=O>CN(C)C=O>[CH2:1]([N:8]1[CH:13]=[CH:12][C:11](=[O:14])[C:10]2[C:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[C:16]([I:28])[O:17][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 58608150HCID 58608150, compound

Product 1

HCID 58608105HCID 58608105, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 7-benzyl-3-phenyl-2-(trimethylsilyl)furo[2,3-b]pyridin-4(7H)-one 4d was taken up in N,N-dimethylformamide (50 mL), and N-Iodosuccinimide (15.704 g, 69.95 mmol) was added. The mixture stirred at room temperature for 1.5 h and was then concentrated. The residue was partitioned between dichloromethane and an aqueous solution of sodium thiosulfate. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford an orange brown oil. Purification via column chromatography on silica gel (eluting with ethyl acetate) afforded 7-benzyl-2-iodo-3-phenylfuro[2,3-b]pyridin-4(7H)-one 4f as a brown solid. MS (MH+) 428.0; Calculated 427 for C20H14INO2.

Workup

  1. concentrationwas then concentrated
  2. customThe residue was partitioned between dichloromethane
  3. customThe aqueous phase was separated
  4. extractionextracted with dichloromethane
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford an orange brown oil
  10. customPurification via column chromatography on silica gel (eluting with ethyl acetate)

Sources & evidence

ORD record
ord-e98a8d3a2f6a412a81232bf2d989227a
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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