Isopropanol → methyl 2-[3-cyano-4-(4-phenyl-1H-1,2,3-triazol-1-yl)phenyl]isonicotinate

HRID 1160830Notes

Reaction equation

HRID 1160830 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=2)[C:13]([O:15][CH3:16])=[O:14])=[CH:6][C:5]=1[C:20]#[N:21])=[N+:2]=[N-:3].[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)#[CH:23].CC(O)C>O.S([O-])([O-])(=O)=O.[Cu+2]>[C:20]([C:5]1[CH:6]=[C:7]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:8]=[CH:9][C:4]=1[N:1]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=[N:2]1)#[N:21]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 10821PhenylacetyleneHCID 86626138Methyl 2-(4-azido-3-cyanophenyl)isonicotinate

Product 1

HCID 68622689methyl 2-[3-cyano-4-(4-phenyl-1H-1,2,3-triazol-1-yl)phenyl]isonicotinate

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent2×

Procedure

200 mg of methyl 2-(4-azido-3-cyanophenyl)isonicotinate, 54 μl of ethynylbenzene, 72 μl of aqueous 1 M sodium L(+)-ascorbate solution and 2 mg of copper sulfate were added to a mixture of 1.4 ml of water and 1.4 ml of 2-propanol, followed by vigorous stirring overnight at room temperature. The reaction mixture was diluted with 5 ml of water, the precipitate formed was collected by filtration, washed with iced cool water, and dried under reduced pressure to obtain 12 mg of methyl 2-[3-cyano-4-(4-phenyl-1H-1,2,3-triazol-1-yl)phenyl]isonicotinate.

Workup

  1. customthe precipitate formed
  2. filtrationwas collected by filtration
  3. washwashed
  4. temperaturewith iced cool water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-f19ee8674f1647dda416a3b6a3d40151
Source dataset
uspto-grants-2010_10
Patent number
US07816558B2

Reaction notes

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