Dichloromethane → HCID 67260951, compound

HRID 2359037Notes

Reaction equation

HRID 2359037 reaction equation
[Br: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[CH2:19][CH:20]([CH3:22])[CH3:21].C(=O)([O-])[O-].[Cs+].[Cs+].ClCCl>CN(C)C=O.O>[CH2:19]([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]([Br:1])=[CH:3][CH:4]=2)=[N:8]1)[CH:20]([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 65551-Bromo-2-methylpropaneHCID 10796Cesium carbonateHCID 178419363HCID 178419363, compound

Product 1

HCID 67260951HCID 67260951, compoundYield 56.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[3-(5-bromo-2-thienyl)-1H-pyrazol-4-yl]pyridine (1 eq, 8.8 mmol) in 50 mL N,N-dimethylformamide were added 1-bromo-2-methylpropane (1.5 eq, 13.2 mmol) and cesium carbonate (1.1 eq, 9.7 mmol). The reaction mixture was stirred overnight at room temperature and poured in 500 mL of water. The resulting precipitate was filtered and dried. The solid was then recristallised in a mixture diisopropylether:dichloromethane to afford 1.81 g of 4-[1-isobutyl-3-(5-bromo-2-thienyl)-1H-pyrazol-4-yl]pyridine (53% yield).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customdried

Sources & evidence

ORD record
ord-5357b1ad14ef4a6bb3dcb50a3a53ba91
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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