Isopropyl iodide → HCID 67260829, compound

HRID 2359031Notes

Reaction equation

HRID 2359031 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=3)=[CH:10][NH:9][N:8]=2)=[CH:4][CH:3]=1.I[CH:19]([CH3:21])[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH:19]([N:9]1[CH:10]=[C:11]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:8]1)([CH3:21])[CH3:20].[CH:19]([N:8]1[C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:11]([C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:10]=[N:9]1)([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 178477995HCID 178477995, compound

Product 2

HCID 67260257HCID 67260257, compoundYield 10%HCID 67260829HCID 67260829, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (1.9 mmol) in 10 mL N,N-dimethylformamide were added 2-iodopropane (2.9 mmol) and cesium carbonate (2.1 mmol). The reaction mixture was stirred overnight at room temperature and the solvent was then evaporated. The residue was diluted with water and extracted three times with ethyl acetate. The combined organic extracts were dried over MgSO4 filtered and concentrated. The residue was purified by chromatography on silica gel (dichloromethane:ethyl acetate 20:1 to 5:1) to afford 0.37 g of 4-[1-isopropyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (61% yield) and 63 mg of 4-[1-isopropyl-5-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (10% yield).

Workup

  1. customthe solvent was then evaporated
  2. additionThe residue was diluted with water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel (dichloromethane:ethyl acetate 20:1 to 5:1)

Sources & evidence

ORD record
ord-7f1dede14b8a4ccc9929d63a6eb0868c
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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