Water → HCID 178470402, compound
Reaction equation
N([O-])=O.[Na+].O.N[C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].[OH-].[Na+].[H+].[B-](F)(F)(F)[F:21]>>[F:21][C:7]1[N:8]=[CH:9][NH:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]Participants
Conditions
- Temperature
- -10 °C
Procedure
Ethyl 4-fluoro-1H-imidazole-5-carboxylate was prepared as described in J. Org. Chem. 1984, 49, 1951. A solution of NaNO2 (76 mg, 2.2 mmol) in minimum amount of H2O was added to a solution of ethyl 4-amino-1H-imidazole-5-carboxylate (310 mg, 2.0 mmol) in 50% HBF4 (7.0 mL) at −10° C. The reaction was stirred for 10 min and then irradiated with medium-pressure mercury vapor lamp (450 W) for 3 h at the same temperature. The mixture was neutralized with NaOH (5N) to Ph=5 while the temperature was maintained at −10° C. The resulting mixture was extracted with EtOAc and the extracts were over sodium sulfate and concentrated. The residue was purified by column chromatography (0-50% EtOAc in Hexane) to give the title compound (50 mg, 16%) as a white solid.
Workup
- customEthyl 4-fluoro-1H-imidazole-5-carboxylate was prepared
- customirradiated with medium-pressure mercury vapor lamp (450 W) for 3 h at the same temperature
- extractionThe resulting mixture was extracted with EtOAc
- concentrationconcentrated
- customThe residue was purified by column chromatography (0-50% EtOAc in Hexane)
Sources & evidence
- ORD record
- ord-eb58e670184d47329672629efdcc2938
- Source dataset
- uspto-grants-2012_11
- Patent number
- US08304419B2
Reaction notes
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