Dimethylformamide → [6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:9]=[N:10][C:11]([Cl:21])=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])([CH3:4])([CH3:3])[CH3:2].[CH3:23]N(C)C=O.CI>>[C:1]([O:5][C:6](=[O:22])[N:7]([C:8]1[CH:9]=[N:10][C:11]([Cl:21])=[CH:12][C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[Cl:20])[CH3:23])([CH3:4])([CH3:2])[CH3:3]Participants
4
Procedure
To a solution of 1.21 g (3.57 mmol) [6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-carbamic acid tert-butyl ester in 35 ml N,N-dimethylformamide 0.18 g (3.7 mmol) sodium hydride (55% dispersion in mineral oil) were added at room temperature. After 30 min 0.25 ml (3.9 mmol) methyl iodide were added and the reaction mixture was stirred for 1 h. Quenching was followed by extraction with tert-butyl methyl ether. The organic layer was washed with two portions of water, and the combined aqueous layers were extracted with two portions of tert-butyl methyl ether. The combined organic layers were dried with sodium sulfate and concentrated to give 1.26 g (100%) of the title compound as a light yellow amorphous mass.
Workup
- customQuenching
- extractionwas followed by extraction with tert-butyl methyl ether
- washThe organic layer was washed with two portions of water
- extractionthe combined aqueous layers were extracted with two portions of tert-butyl methyl ether
- dry with materialThe combined organic layers were dried with sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-8b175499e4524146bcacc3de91c16429
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06770637B2
Reaction notes
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