Potassium Carbonate → 2-(4-iodo-1H-pyrazol-1-yl)-5-nitropyridine

HRID 537578Notes

Reaction equation

HRID 537578 reaction equation
[I:1][C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[I:1][C:2]1[CH:3]=[N:4][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]=2)[CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 770224-IodopyrazoleHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 644297722-(4-iodo-1H-pyrazol-1-yl)-5-nitropyridineYield 100.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the 4-iodo-1H-pyrazole (4.59 g, 23.7 mmol) and 2-chloro-5-nitropyridine (3.75 g, 23.7 mmol) in N,N-dimethylformamide (11.8 ml) was treated with potassium carbonate (3.76 g, 27.2 mmol). The mixture was heated to 80° C. for 12 hours. The reaction mixture was diluted with excess water resulting in the precipitation of a solid that was collected by filtration. Further drying in vacuo afforded the product (7.5 g, 100%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 9.27 (d, J=2.3 Hz, 1H), 8.70 (s, 1H), 8.62 (dd, J=9.0, 2.5 Hz, 1H), 8.12 (d, J=9.0 Hz, 1H), 7.80 (s, 1H).

Workup

  1. filtrationthat was collected by filtration
  2. customFurther drying in vacuo

Sources & evidence

ORD record
ord-0927464c4e03494bb61db8a587de442f
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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