Water → Ethyl 1-(2-fluorophenyl)-5-isopropyl-1H-1,2,3-triazole-4-carboxylate

HRID 219569Notes

Reaction equation

HRID 219569 reaction equation
C1CCN2C(=NCCC2)CC1.[C:12]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])(=O)[CH:13]([CH3:15])[CH3:14].[N:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32])=[N+:24]=[N-:25].O>CN(C=O)C>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[N:23]1[C:12]([CH:13]([CH3:15])[CH3:14])=[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:25]=[N:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81583Ethyl isobutyrylacetateHCID 116079241-Azido-2-fluorobenzene

Product 1

HCID 68649348Ethyl 1-(2-fluorophenyl)-5-isopropyl-1H-1,2,3-triazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

DBU (3.6 ml; 24.07 mmol; 1.10 eq.) was dissolved in DMF (45 ml) and put under nitrogen atmosphere. Ethyl isobutyrylacetate (Aldrich, 3.807 g; 24.07 mmol; 1.10 eq.) was added to the mixture and it was stirred for 15 min. Then a solution of 1-azido-2-fluorobenzene, prepared according to Platz, M. S. et al. J. Org. Chem. 1989, 54, 5938-5945, (3 g; 21.858 mmol; 1 eq.) in DMF (10 mL) was added dropwise to the solution at room temperature. The reaction mixture was stirred at 70° C. for 5 hours. Water (80 mL) was added to the reaction mixture. The aqueous layer was extracted with EtOAc (2×100 mL). Combined organics were washed with HCl 0.1N, brine, dried over MgSO4 and concentrated under vacuum giving the title compound as a brown oil. It was used in the next step without further purification. LC/MS (Method B): 278.2 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at 70° C. for 5 hours
  2. extractionThe aqueous layer was extracted with EtOAc (2×100 mL)
  3. washCombined organics were washed with HCl 0.1N, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b71d95016474453e8541cb1c85129c48
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Reaction notes

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