Dimethylformamide → [6-Chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-carbamic acid tert-butyl ester

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Reaction Steps

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.

Provenance & Evidence