Isopropanol → Ethyl 5-methyl-1,2-diphenyl-1H-imidazole-4-carboxylate
Reaction equation
[C:1]1([NH:7][C:8](=[NH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH:17]([CH2:23]C)[C:18](=O)[C:19]([O-:21])=[O:20].C([O-])(O)=O.[Na+].[CH3:30][CH:31](O)C>>[CH3:23][C:17]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:15][C:18]=1[C:19]([O:21][CH2:30][CH3:31])=[O:20]Participants
5
Conditions
- Temperature
- 90 °C
Procedure
A mixture of N-phenylbenzimidamide (compound 22, 1.0 g, 5.10 mmol), 3-bromo-2-oxovalerate (compound 23, 1.3 g, 6.12 mmol) and NaHCO3 in i-PrOH was stirred at 90° C. for 12 hrs. The reaction mixture was concentrated under reduced pressure, then the residue was diluted with EtOAc and washed with H2O. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography (Biotage Isolera™ FLASH Purification System was used for normal phase column chromatography with EtOAc and hexane) to provide the title compound (0.86 g, 55%) as a yellow solid.
Workup
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionthe residue was diluted with EtOAc
- washwashed with H2O
- dry with materialThe organic layer was dried over anhydrous MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash column chromatography (Biotage Isolera™ FLASH Purification System was used for normal phase column chromatography with EtOAc and hexane)
Sources & evidence
- ORD record
- ord-2230100354204c6ea8c8f083fc2df950
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835436B2
Reaction notes
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