Iodine → 2-Iodofuro[3,2-c]pyridin-4-amine

HRID 2304302Notes

Reaction equation

HRID 2304302 reaction equation
[O:1]1[C:9]2[CH:8]=[CH:7][N:6]=[C:5]([NH2:10])[C:4]=2[CH:3]=[CH:2]1.C([O-])(=O)C.[Na+].[I:16]I.[OH-].[Na+]>C(O)(=O)C.O1CCCC1>[I:16][C:2]1[O:1][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([NH2:10])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 22665882Furo[3,2-c]pyridin-4-amine

Product 1

HCID 226659052-Iodofuro[3,2-c]pyridin-4-amineYield 68.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Furo[3,2-c]pyridin-4-ylamine (7.8 g) was dissolved in 175 mL of glacial acetic acid and sodium acetate (14.3 g) added in portions (exothermic!). Subsequently a solution of iodine (44.2 g) in 150 mL of tetrahydrofuran was added dropwise and the resulting mixture allowed to stir for 4 d at ambient temperature. The mixture was poured on ice and the pH value adjusted to pH 10 by adding 10 N sodium hydroxide solution, followed by extraction with ethyl acetate. The organic extract was washed several times with sodium thiosulfate solution and brine, dried (Na2SO4) and concentrated. The crude product was purified by silica chromatography (ethyl acetate/isohexane=5/5, 7.5/2.5, 10/0) to give 10.3 g (68%) of the title compound as a brownish solid. M.p. 170-173° C.; EI-MS: 260 (M+).

Workup

  1. additionThe mixture was poured on ice
  2. extractionfollowed by extraction with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed several times with sodium thiosulfate solution and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by silica chromatography (ethyl acetate/isohexane=5/5, 7.5/2.5, 10/0)

Sources & evidence

ORD record
ord-8b31d7946ac34d2fbda204f1efa5bc17
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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