Methyl iodide → HCID 71279224, compound
Reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:22](=O)([O-])[O-].[K+].[K+].IC.C(OCC)(=O)C.CCCCCCC>CN(C=O)C>[CH3:22][N:10]1[CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=[C:9]1[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A suspension of tert-butyl 2-(4-phenyl-1H-imidazol-2-yl)ethylcarbamate (1.071 g, 3.73 mmol) and potassium carbonate (1.13 g, 8.2 mmol) in DMF (10 mL) was stirred at 20° C. for 30 min. Then the reaction mixture was cooled to 0-5° C. and iodomethane (280 μl, 4.47 mmol) was added and the resulting mixture was stirred for 30 min. After removal of the ice bath the reaction mixture was stirred at 20° C. for 6 h, poured into water (10 mL) and extracted with dichloromethane (2×20 mL). The organic layers were combined, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (using silica gel amine phase and an ethyl acetate/heptane gradient) to give the product as light yellow solid (835 mg, 2.77 mmol, 74.3%).
Workup
- temperatureThen the reaction mixture was cooled to 0-5° C.
- stirringthe resulting mixture was stirred for 30 min
- customAfter removal of the ice bath the reaction mixture
- stirringwas stirred at 20° C. for 6 h
- additionpoured into water (10 mL)
- extractionextracted with dichloromethane (2×20 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated in vacuo
- customThe crude material was purified by flash chromatography (
Sources & evidence
- ORD record
- ord-492a91bf7b5743fdae735ac57eb751b5
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772510B2
Reaction notes
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