Chloroform → HCID 58608117, compound

HRID 2243579Notes

Reaction equation

HRID 2243579 reaction equation
C([N:8]1[CH:13]=[CH:12][C:11](=O)[C:10]2[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:16]([I:18])[O:17][C:9]1=2)C1C=CC=CC=1.C(Cl)(Cl)[Cl:26].C(Cl)(=O)C(Cl)=O>CN(C)C=O>[Cl:26][C:11]1[CH:12]=[CH:13][N:8]=[C:9]2[O:17][C:16]([I:18])=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:10]=12

Participants

5

Reactant 3

HCID 6212ChloroformHCID 65578Oxalyl chlorideHCID 58608105HCID 58608105, compound

Product 1

HCID 58608117HCID 58608117, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100-ml round bottomed flask equipped with a reflux condenser fitted with a nitrogen inlet adapter was charged with 7-benzyl-2-iodo-3-phenylfuro[2,3-b]pyridin-4(7H)-one 4f (3.08 g, 3.46 mmol) and chloroform (35 mL). Oxalyl chloride (1.76 g, 1.21 mL, 13.84 mmol) and N,N-dimethylformamide (0.20 mL) were added, and the reaction was heated at reflux for 18 h. The reaction mixture was concentrated, and the residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. 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 a black oil. Purification via column chromatography on silica gel (gradient elution with 0-25% ethyl acetate-hexane) afforded 4-chloro-2-iodo-3-phenylfuro[2,3-b]pyridine 6d as a brown oil. MS (MH+) 356.0; Calculated 355 for C13H7ClINO.

Workup

  1. customA 100-ml round bottomed flask equipped with a reflux condenser
  2. customfitted with a nitrogen inlet adapter
  3. temperaturethe reaction was heated
  4. temperatureat reflux for 18 h
  5. concentrationThe reaction mixture was concentrated
  6. customthe residue was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  7. customThe aqueous phase was separated
  8. extractionextracted with dichloromethane
  9. washThe combined organic phases were washed with brine
  10. dry with materialdried over anhydrous sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto afford a black oil
  14. customPurification via column chromatography on silica gel (gradient elution with 0-25% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-b01e72f8d14841328059756b4d263f35
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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