Pyrazole → methyl 2-[3-cyano-4-(1H-pyrazol-1-yl)phenyl]isonicotinate

HRID 1160825Notes

Reaction equation

HRID 1160825 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][C:8]=1F)#[N:2].[NH:20]1[CH:24]=[CH:23][CH:22]=[N:21]1.CC(C)([O-])C.[K+]>CS(C)=O.O>[C:1]([C:3]1[CH:4]=[C:5]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][C:8]=1[N:20]1[CH:24]=[CH:23][CH:22]=[N:21]1)#[N:2]

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 23665647Potassium tert-butoxideHCID 66995083Methyl 2-(3-cyano-4-fluorophenyl)isonicotinate

Product 1

HCID 66995162methyl 2-[3-cyano-4-(1H-pyrazol-1-yl)phenyl]isonicotinateYield 99.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

212 mg of methyl 2-(3-cyano-4-fluorophenyl)isonicotinate and 68 mg of pyrazole were dissolved in 4 ml of DMSO, and 102 mg of potassium tert-butoxide was added, followed by stirring at room temperature for 30 minutes. The reaction mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=67:33) to obtain 251 mg of methyl 2-[3-cyano-4-(1H-pyrazol-1-yl)phenyl]isonicotinate.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=67:33)

Sources & evidence

ORD record
ord-4f9acca778d44c298a3e6ae38dbed93b
Source dataset
uspto-grants-2010_10
Patent number
US07816558B2

Reaction notes

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