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

HRID 219564Notes

Reaction equation

HRID 219564 reaction equation
C1CCN2C(=NCCC2)CC1.[CH2:12]([O:14][C:15](=[O:22])[CH2:16][C:17]([CH:19]1[CH2:21][CH2:20]1)=O)[CH3:13].[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>[CH:19]1([C:17]2[N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[N:24]=[N:25][C:16]=2[C:15]([O:14][CH2:12][CH3:13])=[O:22])[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 262979Ethyl 3-cyclopropyl-3-oxopropanoateHCID 116079241-Azido-2-fluorobenzene

Product 1

HCID 68649104Ethyl 5-cyclopropyl-1-(2-fluorophenyl)-1H-1,2,3-triazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

DBU (2.99 ml; 20.06 mmol; 1.10 eq.) was dissolved in DMF (37.5 ml) and put under nitrogen atmosphere. 3-Cyclopropyl-3-oxo-propionic acid ethyl ester (Betapharma, 3.132 g; 20.06 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, (2.5 g; 18.23 mmol; 1 eq.) in DMF (5 mL) was added dropwise to the solution at room temperature. Water (50 mL) was added to the cooled reaction mixture and the aqueous layer was extracted with EtOAc (3×50 mL). Combined organics were washed with water and brine, dried over MgSO4 and concentrated under vacuum affording the title compound as a brown oil. It was used in the next step without further purification. LC/MS (Method B): 276.1 (M+H)+.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
  2. washCombined organics were washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-59ffb5b717d145edbe0ffa8943f7b38d
Source dataset
uspto-grants-2012_06
Patent number
US08202856B2

Reaction notes

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