Pyrazole → HCID 86758112, compound

HRID 2184908Notes

Reaction equation

HRID 2184908 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](/[C:9](/[CH2:16]Br)=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[NH:18]1[CH:22]=[CH:21][CH:20]=[N:19]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5](/[C:9](/[CH2:16][N:18]2[CH:22]=[CH:21][CH:20]=[N:19]2)=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 86758110HCID 86758110, compound

Product 1

HCID 86758112HCID 86758112, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl (Z) 3-(3-cyanophenyl)-4-bromo-2-butenoate (103 mg, 0.35 mmol) in 5 ml anhydrous di-methylformamide was added pyrazole (24 mg, 0.35 mmol) and cesium carbonate (228 mg, 0.7 mmol). Reaction mixture was stirred for 1.5 hours at room temperature after which 25 ml ethyl acetate was added. Organic was washed with 3×25 ml water, 3×50 ml saturated brine solution, dried over magnesium sulfate, filtered and concentrated to give ethyl (Z)-3-(3-cyanophenyl)-4-(1H-1-pyrazolyl)-2-butenoate (70 mg, 71%) as a brown residue which was sufficiently pure to be used without further purification. ES-MS (M+H+): 282.1

Workup

  1. customReaction mixture
  2. additionwas added
  3. washOrganic was washed with 3×25 ml water, 3×50 ml saturated brine solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4e6ecddf6405465ea365d3ef2c5df07c
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

Loading…