Ethyl Acetate → HCID 66679602, compound

HRID 1842572Notes

Reaction equation

HRID 1842572 reaction equation
[I:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.F[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([N:4]2[CH:5]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]([I:1])=[N:3]2)=[N:14][CH:15]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 27628712,5-DifluoropyridineHCID 178469927HCID 178469927, compound

Product 1

HCID 66679602HCID 66679602, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 3-iodo-1H-pyrazole-4-carboxylate (8.5 g, 32.0 mmol) in DMF (160 mL) was added 2,5-difluoropyridine (11.0 g, 96.0 mmol) and potassium carbonate (13.3 g, 96.0 mmol). The mixture was stirred at 100° C. in a sealed reaction flask. After 18 h, the mixture was cooled to ambient temperature and ethyl acetate and water were added. The solid in the organic layer was filtered off and the filtrate was dried over MgSO4, filtered and concentrated. The product was recrystallized using ethyl acetate and ether to give 6.5 g of the title compound. The solution from recrystallization was concentrated and purified by silica gel chromatography (100% dichloromethane→98% dichloromethane/methanol) gave 0.8 g of the title compound (7.3 g total). MS 361.8 (M+1).

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. filtrationThe solid in the organic layer was filtered off
  3. dry with materialthe filtrate was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was recrystallized

Sources & evidence

ORD record
ord-8ca226e2055e491783def04f26064237
Source dataset
uspto-grants-2015_02
Patent number
US08946231B2

Reaction notes

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