Sodium Iodide → 1-(4-Iodo-pyrazolo[3,4-b]pyridin-1-yl)ethanone

HRID 724437Notes

Reaction equation

HRID 724437 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.[I-:11].[Na+].[C:13](Cl)(=[O:15])[CH3:14].OS([O-])=O.[Na+]>C(#N)C>[I:11][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([C:13](=[O:15])[CH3:14])[N:9]=[CH:10][C:3]=12

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6367Acetyl chlorideHCID 3100454-Chloro-1H-pyrazolo[3,4-b]pyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 218774001-(4-Iodo-pyrazolo[3,4-b]pyridin-1-yl)ethanoneYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-1H-pyrazolo[3,4-b]pyridine (820 mg, 5.30 mmol), sodium iodide (2.4 mg, 16.0 mmol), and acetyl chloride (0.8 ml) in acetonitrile (6 ml) was refluxed 8 h. The mixture was then treated with a 10% aqueous solution of NaCO3 (10 ml), and a 10% aqueous solution of NaHSO3 (10 ml), and held 10 min. The mixture was extracted with ethyl acetate (50 ml), and the organics were washed with brine (10 ml), dried over MgSO4, and evaporated under reduced pressure. Purification by silica gel chromatography gave 1-(4-iodo-pyrazolo[3,4-b]pyridin-1-yl)-ethanone as a brown solid (650 mg, 42%). 1H NMR (300 MHz, CDCl3) δ 8.39 (d, 1H, J=5.0 Hz), 8.04 (s, 1H), 7.76 (d, 1H, J=5.0 Hz), 2.88 (s, 3H).

Workup

  1. temperaturewas refluxed 8 h
  2. extractionThe mixture was extracted with ethyl acetate (50 ml)
  3. washthe organics were washed with brine (10 ml)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-5c5e4f82afa14fedaf5fb02f98d54cdd
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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