Pyrazole → 5-Bromo-3-nitro-2-(1H-pyrazol-1-yl)pyridine

HRID 1443858Notes

Reaction equation

HRID 1443858 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[NH:12]1[CH:16]=[CH:15][CH:14]=[N:13]1>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([N:12]2[CH:16]=[CH:15][CH:14]=[N:13]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 1048PyrazoleHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 263699265-Bromo-3-nitro-2-(1H-pyrazol-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 5-bromo-2-chloro-3-nitropyridine (10 g, 42 mmol) in 1,4-dioxane (100 ml) was added pyrazole (5.8 g, 85 mmol). The resulting mixture was stirred at 120° C. for 26.5 h., and then evaporated after cooling to r.t. The crude material was purified by flash chromatography (0 to 5% EtOAc/Hexanes) to give the desired product 5-Bromo-3-nitro-2-pyrazol-1-yl-pyridine. 1H NMR: (CD3OD) δ 8.77 (s, 1H), 8.56 (s, 1H), 8.45 (s, 1H), 7.73 (s, 1H), 6.57 (s, 1H); LC/MS: (ES+) m/z (M+H)+=269, 271, HPLC Rt=1.223.

Workup

  1. customevaporated
  2. temperatureafter cooling to r.t
  3. customThe crude material was purified by flash chromatography (0 to 5% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-053c51d0f156485e8a50d39dc9346df7
Source dataset
uspto-grants-2010_02
Patent number
US07662823B2

Reaction notes

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