Potassium Carbonate → 5-(2H-1,2,3-Triazol-2-yl)indan-1-one

HRID 1913409Notes

Reaction equation

HRID 1913409 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[NH:12]1[CH:16]=[CH:15][N:14]=[N:13]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O.[Cu]=O>[N:12]1[N:13]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[CH2:6][CH2:5]3)[N:14]=[CH:15][CH:16]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 5206955-Bromo-1-indanoneHCID 178418936HCID 178418936, compound

Product 1

HCID 584384785-(2H-1,2,3-Triazol-2-yl)indan-1-oneYield 55%

Reagents, catalysts & solvents 4

HCID 14829Copper oxideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-1-indanone (5.0 g, 24 mmol) and 1H-triazole (4.90 g, 71.1 mmol) in 20 mL of DMF was added Fe(acac)3 (838 mg, 2.37 mmol), copper (II) oxide (188 mg, 2.36 mmol) and potassium carbonate (3.27 g, 23.7 mmol). The reaction mixture was degassed with nitrogen for 10 minutes. The mixture was stirred at 90° C. for 6.5 hours and at 80° C. for 15 hours. The cooled reaction mixture was diluted with ethyl acetate and water. The biphasic mixture was passed through a thin Celite® pad, which was washed thoroughly with ethyl acetate. The combined organic layers were washed with water, brine and dried over anhydrous magnesium sulfate. Filtration and solvent removal afforded the crude product which was purified by silica chromatography using an ISCO (Teledyne Isco Inc., Lincoln Nebr.) column eluting with a 0-40% ethyl acetate/heptanes gradient to give the desired product as a pale yellow solid (2.60 g, 55%). MS (ES+) 200.1 (M+H)+. 1H NMR (CDCl3) δ 2.85 (t, 2H), 3.24 (t, 2H), 7.83-7.90 (m, 3H), 8.15 (d, 1H), 8.21 (s, 1H).

Workup

  1. customThe reaction mixture was degassed with nitrogen for 10 minutes
  2. customThe cooled reaction mixture
  3. washwas washed thoroughly with ethyl acetate
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration and solvent removal
  7. customafforded the crude product which
  8. customwas purified by silica chromatography
  9. washeluting with a 0-40% ethyl acetate/heptanes gradient

Sources & evidence

ORD record
ord-ca837d218a404d51aedc82791be6a68e
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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