N-Iodosuccinimide → 2-Chloro-3-iodopyrazolo[1,5-A]pyridine

HRID 530015Notes

Reaction equation

HRID 530015 reaction equation
[Cl:1][C:2]1[CH:10]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[I:11]N1C(=O)CCC1=O>C(#N)C>[Cl:1][C:2]1[C:10]([I:11])=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 122844332-Chloropyrazolo[1,5-a]pyridine

Product 1

HCID 717433402-Chloro-3-iodopyrazolo[1,5-A]pyridine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-pyrazolo[1,5-a]pyridine (0.500 g, 3.28 mmol) in acetonitrile (16.4 mL) was added N-iodosuccinimide (0.885 g, 3.93 mmol). The resulting mixture was stirred at room temperature for 2 hours, then concentrated under reduced pressure. The resulting residue was diluted with dichloromethane, washed with saturated aqueous sodium chloride solution, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by flash chromatography on silica gel (0-15% ethyl acetate in hexanes) provided the title compound. LCMS m/z 278.72 [M+H]+, 280.64 [M+2+H]+, 1H NMR (500 MHz, CDCl3) 8.35 (d, J=6.8 Hz, 1 H), 7.38 (d, J=9.0 Hz, 1H), 7.24 (d, J=8.6 Hz, 1 H), 6.84-6.81 (m, 1 H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting residue was diluted with dichloromethane
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by flash chromatography on silica gel (0-15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7895939d8b494ae0b01a25432ada00a1
Source dataset
uspto-grants-2016_05
Patent number
US09351973B2

Reaction notes

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