Cesium carbonate → HCID 86657919, compound

HRID 2359033Notes

Reaction equation

HRID 2359033 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:13]3[S:14][C:15]([Cl:18])=[CH:16][CH:17]=3)=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].ClC1[CH:31]=[C:30]([C:32]2C(C3SC(Cl)=CC=3)=NN(CC(C)C)C=2)[CH:29]=CN=1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:12]=[N:11][N:10]([CH2:29][CH:30]([CH3:32])[CH3:31])[C:9]=2[C:13]2[S:14][C:15]([Cl:18])=[CH:16][CH:17]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 86657920HCID 86657920, compoundHCID 178477882HCID 178477882, compound

Product 1

HCID 86657919HCID 86657919, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-4-[3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (6.7 mmol) in 53 mL N,N-dimethylformamide were added bromoisobutyle (10.1 mmol) and cesium carbonate (7.4 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 (heptane:ethyl acetate 1:0 to 1:1) to afford 2.21 g of a mixture of 2-chloro-4-[1-isobutyl-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine and 2-chloro-4-[1-isobutyl-5-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (8:2; 88% yield). The mixture was used as such in the next step.

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 (heptane:ethyl acetate 1:0 to 1:1)

Sources & evidence

ORD record
ord-f5e5c72885034f7fa0c89731d5ae021b
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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