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

HRID 530031Notes

Reaction equation

HRID 530031 reaction equation
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:18]=[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=1>C(#N)C>[Cl:9][C:10]1[C:18]([I:1])=[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=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

N-iodosuccinimide (1.06 g, 4.74 mmol) was added to a solution of 2-chloro-pyrazolo-[1,5-a]pyridine (27-2; 0.6 g, 3.95 mmol) in acetonitrile (18.0 mL). The resulting mixture was stirred at room temperature for 2 h and then concentrated under reduced pressure. The resulting residue was diluted with dichloromethane, washed with saturated aqueous sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by silica gel flash chromatography (5-10% ethyl acetate in hexanes) provided the title compound. 1H NMR (400 MHz, CDCl3) δ 8.36-8.34 (d, J=6.8 Hz, 1 H), 7.40-7.37 (d, J=8.8 Hz, 1 H), 7.26-7.23 (m, 1 H), 6.84-6.81 (m, 1 H). MS (M+1): 279.0.

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 magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel flash chromatography (5-10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-026fe51dfcaf49f395c19ad0b857de4e
Source dataset
uspto-grants-2016_05
Patent number
US09351973B2

Reaction notes

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