Ethyl Acetate → HCID 67260874, compound

HRID 2359049Notes

Reaction equation

HRID 2359049 reaction equation
[Br:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[S:14][C:13]([C:15]2[C:19]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:18][NH:17][N:16]=2)=[CH:12][CH:11]=1.C(OCC)(=O)C>CN(C)C=O>[Br:1][C:18]1[NH:17][N:16]=[C:15]([C:13]2[S:14][C:10]([Cl:9])=[CH:11][CH:12]=2)[C:19]=1[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimide2×HCID 178477995HCID 178477995, compound

Product 1

HCID 67260874HCID 67260874, compoundYield 123.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-Bromosuccinimide (1 eq, 0.38 mmol) was added to a solution of 4-[3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine (1 eq, 0.38 mmol) in 2 mL of N,N-dimethylformamide. The mixture was then stirred at 80° C. for 2 h. Further N-Bromosuccinimide (0.3 eq, 0.12 mmol) was added and the mixture was stirred for one more hour. After cooling to room temperature, ethyl acetate was added and the organic layer was washed with water, dried over MgSO4, filtered and evaporated. The residue was suspended in diisopropylether and dichloropethane, filtered and dried in a vacuum oven at 50° C. to afford 0.16 g of 4-[5-bromo-3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]pyridine.

Workup

  1. stirringthe mixture was stirred for one more hour
  2. temperatureAfter cooling to room temperature
  3. washthe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. filtrationdichloropethane, filtered
  8. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-bc524d7736a14ac5a9c322bfb21fcbae
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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