Isopropyl iodide → 1H-Imidazole-5-carboxaldehyde,1-(1-methylethyl)-(9CI)
Reaction equation
[NH:1]1[C:5]([CH:6]=[O:7])=[CH:4][N:3]=[CH:2]1.I[CH:9]([CH3:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:9]([N:1]1[C:5]([CH:6]=[O:7])=[CH:4][N:3]=[CH:2]1)([CH3:11])[CH3:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 1H-imidazole-5-carbaldehyde (800 mg, 8.3 mmol), 2-iodopropane (1.7 g, 10 mmol) and potassium carbonate (1.4 g) in DMF (30 mL) was heated to 50° C. overnight. The mixture was evaporated under reduced pressure, and then extracted with ethyl acetate (100 mL×4). The combined organic layers were dried over anhydrous sodium sulfate, concentrated to give 1-isopropyl-1H-imidazole-5-carbaldehyde (1.1 g), LC-MS (ESI) m/z: 139 (M+1)+. This compound (1.1 g, 8.0 mmol) and (E)-4-(benzylideneamino)isobenzofuran-1(3H)-one (1.7 g, 7.2 mmol) were added in ethyl propionate (50 mL) then sodium ethoxide was added under 0° C. The mixture was stirred overnight at room temperature. The mixture was concentrated and the residue was extracted with ethyl acetate (100 mL×4). The organic layer dried over anhydrous sodium sulfate, purified by chromatography (silica gel, petroleum ether/ethyl acetate=10:1 to 1:1) to give ethyl 3-(1-isopropyl-1H-imidazol-5-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (770 mg, yield 30%). LC-MS (ESI) m/z: 404 (M+1)+.
Workup
- customThe mixture was evaporated under reduced pressure
- extractionextracted with ethyl acetate (100 mL×4)
- dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d5a55dc1f123466abc658986de46e688
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420650B2
Reaction notes
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