Potassium Carbonate → ethyl 4-(4-phenyl-1H-pyrazol-1-yl)butanoate

HRID 1664582Notes

Reaction equation

HRID 1664582 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:10]1([C:16]2[CH:17]=[N:18][NH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:10]1([C:16]2[CH:17]=[N:18][N:19]([CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:20]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 1391064-Phenylpyrazole

Product 1

HCID 66725907ethyl 4-(4-phenyl-1H-pyrazol-1-yl)butanoateYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The mixture of ethyl 4-bromobutyrate (0.400 g, 2.05 mmole), 4-phenyl-1H-pyrazole (0.296 g, 2.05 mmole) and K2CO3 (0.567 g, 4.10 mmole) in DMF (10 ml) was stirred at room temperature overnight. The reaction mixture was diluted with water (100 ml) and extracted with ethyl acetate (2×). The combined organic phases were washed with water and then brine, dried over Na2SO4, filtered and concentrated to give the crude product, which was purified by preparative to afford the desired product (73 mg, 52%) as colorless oil. LCMS calculated for C15H19N2O2 (M+H): 259. found: 259.1.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washThe combined organic phases were washed with water
  3. dry with materialbrine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas purified by preparative

Sources & evidence

ORD record
ord-efe75539ce124189b1094d90b8c1b03f
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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