N-Iodosuccinimide → HCID 57837525, compound

HRID 731737Notes

Reaction equation

HRID 731737 reaction equation
[CH:1]([C:4]1[CH:12]=[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][N:6]2[N:5]=1)([CH3:3])[CH3:2].[I:13]N1C(=O)CCC1=O>ClCCCl.O1CCCC1>[I:13][C:12]1[C:4]([CH:1]([CH3:3])[CH3:2])=[N:5][N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 113786582-Isopropylpyrazolo[1,5-a]pyridine

Product 1

HCID 57837525HCID 57837525, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Isopropyl-pyrazolo[1,5-a]pyridine (18.42 g, 115 mmol) and N-iodosuccinimide (28.45 g, 126 mmol) were dissolved in a mixture of 1,2-dichloroethane (300 ml) and tetrahydrofuran (300 ml). The mixture was stirred at reflux for 18 hours. The mixture was cooled and concentrated in vacuo. The crude material was purified by silica gel flash chromatography (0 to 20% ethyl acetate in hexanes) to give 30.9 g (94%) of 3-iodo-2-isopropyl-pyrazolo[1,5-a]pyridine. 1H-NMR (250 MHz, CDCl3) δ 8.36 (d, J=7.0 Hz, 1H), 7.36 (d, J=9.0 Hz, 1H), 7.12 (t, J=7.9 Hz, 1H), 6.67 (t, J=7.6 Hz, 1H), 3.20 (sept, J=7.0 Hz, 1H), 1.37 (d, J=6.8 Hz, 6H).

Workup

  1. temperatureat reflux for 18 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by silica gel flash chromatography (0 to 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-bf1fae3828b44c7b90f9bf65fc64201f
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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