Methyl iodide → n-Cyclobutyl-5-(2,6-dichloro-4-methoxymethyl-phenoxy)-2-methoxy-n-methyl-benzamide
Reaction equation
[CH:1]1([NH:5][C:6](=[O:27])[C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:19]([Cl:20])=[CH:18][C:17]([CH2:21][O:22][CH3:23])=[CH:16][C:15]=3[Cl:24])[CH:10]=[CH:9][C:8]=2[O:25][CH3:26])[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:30]I>CN(C)C=O.Cl>[CH:1]1([N:5]([CH3:30])[C:6](=[O:27])[C:7]2[CH:12]=[C:11]([O:13][C:14]3[C:19]([Cl:20])=[CH:18][C:17]([CH2:21][O:22][CH3:23])=[CH:16][C:15]=3[Cl:24])[CH:10]=[CH:9][C:8]=2[O:25][CH3:26])[CH2:4][CH2:3][CH2:2]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the title compound of Step E (170 mg, 0.41 mmol) in dimethylformamide (4 ml) at 0° C. under nitrogen was added sodium hydride (60% dispersion in mineral oil, 41 mg, 1 mmol). The resulting slurry mixture was stirred at 0° C. for about 30 minutes and gradually became a brownish-yellow solution. To this solution at 0° C. was added methyl iodide (0.13 ml, 2 mmol). The resulting solution was warmed to room temperature and stirred for about 19 hours. The solution was diluted with 1N HCl (30 ml) and extracted with ethyl acetate (3×15 ml). The combined organic extracts were washed with 1N HCl (3×50 ml), brine, dried, filtered, and concentrated. The residue was purified by preparative TLC (50% ethyl acetate in hexanes) to afford the title compound (155 mg). MS (APCl+) Calc: 423.1, found: 424.0 (M+1).
Workup
- temperatureThe resulting solution was warmed to room temperature
- stirringstirred for about 19 hours
- extractionextracted with ethyl acetate (3×15 ml)
- washThe combined organic extracts were washed with 1N HCl (3×50 ml), brine
- customdried
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by preparative TLC (50% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-c812e14bb2c346aa9e1ea5e4f5393c1e
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06620830B2
Reaction notes
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