Isopropyl iodide → HCID 67260328, compound

HRID 2359036Notes

Reaction equation

HRID 2359036 reaction equation
[F: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]([F: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]([F: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 178505590HCID 178505590, compound

Product 2

HCID 67260328HCID 67260328, compoundYield 64%HCID 67260796HCID 67260796, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[3-(5-fluoro-2-thienyl)-1H-pyrazol-4-yl]pyridine (0.61 mmol) in 3 mL N,N-dimethylformamide were added 2-iodopropane (0.91 mmol) and cesium carbonate (0.67 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 ether. 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 114 mg of 4-[1-isopropyl-3-(5-fluoro-2-thienyl)-1H-pyrazol-4-yl]pyridine (64% yield) and 4 mg of 4-[1-isopropyl-5-(5-fluoro-2-thienyl)-1H-pyrazol-4-yl]pyridine (3% yield).

Workup

  1. customthe solvent was then evaporated
  2. additionThe residue was diluted with water
  3. extractionextracted three times with ethyl ether
  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-3718478461084b4c97f5ca9fdcdf145d
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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