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

HRID 219565Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[N:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16])=[N+:8]=[N-:9].[O:17]1[CH2:21][CH2:20][CH2:19][CH:18]1[C:22](=O)[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CS(C)=O>[F:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:7]1[C:22]([CH:18]2[CH2:19][CH2:20][CH2:21][O:17]2)=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:9]=[N:8]1

Participants

Conditions

Temperature: 70 °C

Procedure

Potassium carbonate (2.419 g; 17.50 mmol; 2 eq.) was dissolved in DMSO (18 ml) and put under nitrogen atmosphere. 1-Azido-2-fluorobenzene, prepared according to Platz, M. S. et al. J. Org. Chem. 1989, 54, 5938-5945, (1.2 g; 8.75 mmol; 1 eq.) was dissolved in 10 mL of DMSO and ethyl 3-(tetrahydrofuran-2-yl)-3-oxopropanoate (Pharmacore, 1.793 mg; 9.63 mmol; 1.10 eq.) was added. This solution was added dropwise to the potassium carbonate solution at room temperature. The mixture was stirred at 70° C. for 3 hours. Water (30 mL) was added to the mixture and it was extracted with EtOAc (2×40 mL). Organics were washed with 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. HPLC (Method A) Rt 4.14 min (Purity: 86.6%).

Workup

extractionwas extracted with EtOAc (2×40 mL)
washOrganics were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-4297ff5b96fd428f97dff354b5c6ac86
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202856B2

Reaction notes

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