N-Iodosuccinimide → 4-Iodofuro[2,3-c]pyridin-7-amine

HRID 389483Notes

Reaction equation

HRID 389483 reaction equation
[O:1]1[C:5]2=[C:6]([NH2:10])[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C1C(=O)N([I:18])C(=O)C1>C(#N)C>[I:18][C:9]1[CH:8]=[N:7][C:6]([NH2:10])=[C:5]2[O:1][CH:2]=[CH:3][C:4]=12

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 23402647Furo[2,3-c]pyridin-7-amine

Product 1

HCID 667598494-Iodofuro[2,3-c]pyridin-7-amineYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of furo[2,3-c]pyridine-7-ylamine (1.5 g, 11.2 mmol) in acetonitrile (40 mL) was added NIS (3.02 g, 13.4 mmol) portionwise over a period of 15 min. The resultant mixture was stirred at RT for 16 h. The reaction mixture was quenched with 20% aqueous sodium thiosulfate solution (20 mL) and stirred for 10 min. The mixture was extracted with ethyl acetate (70 mL). The organic layer was washed with aqueous 20% sodium thiosulfate solution (20 mL), water (2×50 mL), and brine (40 mL), dried over sodium sulfate, filtered, and concentrated. Purification of the residue by column chromatography (25% ethyl acetate:hexanes) afforded 2.5 g (86%) of the title compound.

Workup

  1. customThe reaction mixture was quenched with 20% aqueous sodium thiosulfate solution (20 mL)
  2. extractionThe mixture was extracted with ethyl acetate (70 mL)
  3. washThe organic layer was washed with aqueous 20% sodium thiosulfate solution (20 mL), water (2×50 mL), and brine (40 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by column chromatography (25% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-2dd0ae2e514940e08f4c2a58b56807c9
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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