N-Iodosuccinimide → HCID 66779473, compound

HRID 503589Notes

Reaction equation

HRID 503589 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([Si](C)(C)C)[O:10][C:3]=12.C1C(=O)N([I:22])C(=O)C1.[F-].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([I:22])[O:10][C:3]=12

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 522689Potassium FluorideHCID 594273397-Chloro-2-(trimethylsilyl)furo[3,2-b]pyridine

Product 1

HCID 66779473HCID 66779473, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7-Chloro-2-(trimethylsilyl)furo[3,2-b]pyridine (0.250 g, 1.11 mmol) and NIS (2.49 g, 11.1 mmol) were dissolved in 3 mL of ACN and stirred for 5 minutes. Potassium fluoride (0.0708 g, 1.22 mmol) was added and the reaction was stirred at 50° C. for one hour. The reaction was concentrated, redissolved in ethyl acetate, and washed with saturated sodium thiosulfate, water and brine. The organic layer was dried with sodium sulfate, filtered, and concentrated. The crude material was purified via column chromatography (gradient elution 0-100% EtOAc:Hex) to afford 7-chloro-2-iodofuro[3,2-b]pyridine as a white solid. MS: M+H+=280.2.

Workup

  1. stirringthe reaction was stirred at 50° C. for one hour
  2. concentrationThe reaction was concentrated
  3. dissolutionredissolved in ethyl acetate
  4. washwashed with saturated sodium thiosulfate, water and brine
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified via column chromatography (gradient elution 0-100% EtOAc:Hex)

Sources & evidence

ORD record
ord-b20e5367d3584dd89867de49cf6d095e
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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