Potassium Carbonate → HCID 67086543, compound

HRID 2174993Notes

Reaction equation

HRID 2174993 reaction equation
F[C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N:11]1[NH:12][N:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:10][C:9]1[C:2]([N:12]2[N:13]=[CH:14][CH:15]=[N:11]2)=[C:3]([CH:6]=[CH:7][CH:8]=1)[C:4]#[N:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 675161H-1,2,3-TriazoleHCID 231603592-Fluoro-3-methylbenzonitrile

Product 1

HCID 67086543HCID 67086543, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 2-fluoro-3-methylbenzonitrile (4.0 g, 29.6 mmol) and 2H-1,2,3-triazole (2.04 g, 29.6 mmol) in DMF (80 mL) was added potassium carbonate (8.26 g, 59.2 mmol). The resulting mixture was heated to 120° C. for 2 h. The mixture was cooled, diluted with water and extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (SiO2, ethyl acetate/hexanes, gradient 0-50%) to yield the title compound (1.5 g, 26%). MS (ESI) mass calcd. for C10H8N4, 184.2; m/z found, 185.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.95 (s, 2H), 7.66 (d, J=7.7, 0.7 Hz, 1H), 7.59 (d, J=7.8, 0.6 Hz, 1H), 7.50 (dd, J=9.8, 5.7 Hz, 1H), 2.20 (s, 3H).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by FCC (SiO2, ethyl acetate/hexanes, gradient 0-50%)

Sources & evidence

ORD record
ord-b6552bbd86b643a981dd9adae116c5f9
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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