Cesium carbonate → 2-(3-methyl-1H-indazol-1-yl)benzonitrile

HRID 1481888Notes

Reaction equation

HRID 1481888 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[CH3:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][N:9]=1.F[C:18]1[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=1[C:20]#[N:21]>CN(C=O)C.[NH4+].[Cl-]>[CH3:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([C:18]2[CH:25]=[CH:24][CH:23]=[CH:22][C:19]=2[C:20]#[N:21])[N:9]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 678552-FluorobenzonitrileHCID 178434273HCID 178434273, compound

Product 1

HCID 900375452-(3-methyl-1H-indazol-1-yl)benzonitrileYield 89.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Cs2CO3 (1.56 g, 4.8 mmol) was added to a solution of 3-methyl indazole (0.634 g, 4.8 mmol) and 2-fluorobenzonitrile (1 mL, 9.6 mmol) in DMF (20 mL). After 12 h the mixture was diluted with sat. NH4Cl and a precipitate formed. The solid was filtered, washed with H2O, hexane and dried under vacuum to give 2-(3-methyl-1H-indazol-1-yl)benzonitrile (1 g, 89%) which was used without purification.

Workup

  1. customa precipitate formed
  2. filtrationThe solid was filtered
  3. washwashed with H2O, hexane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-3945abfd7b1341d89b985353e7562b8f
Source dataset
uspto-grants-2016_08
Patent number
US09409888B2

Reaction notes

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