Potassium Carbonate → HCID 178511383, compound

HRID 1471904Notes

Reaction equation

HRID 1471904 reaction equation
[C:1]1([C:7]2[CH2:11][C:10](=[O:12])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:14][C:15]#[N:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:1]1([C:7]2[CH:11]=[C:10]([O:12][CH2:14][C:15]#[N:16])[NH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 785775-Phenyl-4H-pyrazol-3-ol

Product 1

HCID 178511383HCID 178511383, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-phenyl-1H-pyrazol-5(4H)-one (1.00 g, 6.24 mmol) in DMF (5.0 mL) was added 2-bromoacetonitrile (0.520 mL, 7.80 mmol) and K2CO3 (0.863 g, 6.24 mmol). The reaction was stirred at 25° C. for 12 h, quenched with water (40.0 mL), extracted with EtOAc (3×50.0 mL) and washed with brine. The combined organics were dried over MgSO4, filtered, and concentrated to give the title compound as a yellow oil. This yellow oil was purified by silica gel flash chromatography to give the title compound as a clear oil (0.990 g). LCMS m/z=200.3 [M+H]+.

Workup

  1. customquenched with water (40.0 mL)
  2. extractionextracted with EtOAc (3×50.0 mL)
  3. washwashed with brine
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-359c0623da4248698bf27c564fcff170
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

Loading…