N-Iodosuccinimide → HCID 66779473, compound

HRID 1042854Notes

Reaction equation

HRID 1042854 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-d8a13e5a455b4a93afcf2e5a8c070132
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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