Potassium Carbonate → HCID 9921211, compound

HRID 2213324Notes

Reaction equation

HRID 2213324 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[N:2]1.C(=O)([O-])[O-].[K+].[K+].F[C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23]>CN(C=O)C>[N:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:3]1[N:4]=[CH:5][N:1]([C:19]2[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=2)[C:22]#[N:23])[N:2]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 678803-FluorobenzonitrileHCID 178420161HCID 178420161, compound

Product 1

HCID 9921211HCID 9921211, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
145 °C

Procedure

2-(1H-1,2,4-Triazol-3-yl)pyridine (0.24 g, 1.6 mmol), potassium carbonate (0.45 g, 3.2 mmol) and 3-fluorobenzonitrile (0.20 g, 1.6 mmol) were stirred in DMF (20 mL) at ambient temperature. The resulting reaction mixture was heated at 145° C. for 16 h, after which time it was quenched with H2O (30 mL) and diluted with EtOAc (200 mL). The EtOAc solution was washed with H2O (3×100 mL), then brine (100 mL) and dried (MgSO4), filtered, and concentrated in vacuo. The resulting residue was chromatographed on silica gel eluting with hexane:EtOAc (40:60) to afford 3-(3-pyridin-2-yl-1H-1,2,4-triazol-1-yl)benzonitrile as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. customafter which time it was quenched with H2O (30 mL)
  3. additiondiluted with EtOAc (200 mL)
  4. washThe EtOAc solution was washed with H2O (3×100 mL)
  5. dry with materialbrine (100 mL) and dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was chromatographed on silica gel eluting with hexane:EtOAc (40:60)

Sources & evidence

ORD record
ord-9ad3c0d5134a412b8df25da103bfbd1c
Source dataset
uspto-grants-2006_09
Patent number
US07105548B2

Reaction notes

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