Sodium Chloride → 5-Chloro-2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)pyridine

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Reaction Steps

To a tetrahydrofuran (350 ml) solution of 5-chloropyridin-2-ylamine (10.28 g, 80.0 mmol) was added a hexane solution (1.58M, 50.6 ml, 80.0 mmol) of n-butyl lithium at −78° C. The resulting mixture was stirred for 1 hour. At the same temperature, a tetrahydrofuran (50 ml) solution of 1,2-bis(chlorodimethylsilyl)ethane (17.22 g, 80.0 mmol) was added to the reaction mixture, followed by stirring for 1 hour. A hexane solution (1.58M, 50.6 ml, 80.0 mmol) of n-butyl lithium was added at the same temperature and the resulting mixture was stirred for 30 minutes. At room temperature, a saturated aqueous solution of sodium chloride was added to the reaction mixture. Diethyl ether was added to the resulting mixture to separate it into layers. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was distilled under reduced pressure (120° C./3.0 mmHg) to give the title compound (12.97 g, 47.9 mmol, 60%) as a colorless acicular substance.

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