2-Bromobutane → HCID 67260260, compound

HRID 2359035Notes

Reaction equation

HRID 2359035 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.Br[CH:19]([CH2:21][CH3:22])[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)([CH2:21][CH3:22])[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)([CH2:21][CH3:22])[CH3:20]

Participants

6

Reactant 3

HCID 65542-BromobutaneHCID 10796Cesium carbonateHCID 178505590HCID 178505590, compound

Product 2

HCID 67260260HCID 67260260, compoundYield 60%HCID 67260973HCID 67260973, compoundYield 16%

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-bromobutane (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 112 mg of 4-[1-secbutyl-3-(5-fluoro-2-thienyl)-1H-pyrazol-4-yl]pyridine (60% yield) and 30 mg of 4-[1-secbutyl-5-(5-fluoro-2-thienyl)-1H-pyrazol-4-yl]pyridine (16% 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-118cc22a3def489cb44808566ff7d84f
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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