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ChemicalBook CAS DataBase List 2-amino-5-trimethylsilanylethynylpyridine

2-amino-5-trimethylsilanylethynylpyridine synthesis

3synthesis methods
-

Yield:457628-40-9 95%

Reaction Conditions:

with bis-triphenylphosphine-palladium(II) chloride;copper(l) iodide;triethylamine in N,N-dimethyl-formamide at 20; for 1 h;Inert atmosphere;

Steps:

44

The mixture of 2-amino-5-iodopyridine (1 g, 4.52 mmol, 1.0 eq.) and CuI (0.08 g, 0.41 mmol, 0.09 eq.) was dispersed in 50 ml of N,N-dimethylformamide. In under nitrogen atmosphere, were addedbis(triphenylphosphine) palladium dichloride (0.3 g, 0.41 mmol, 0.09 eq.), triethylamine (2 ml, 14.3 mmol, 3.0 eq) and trimethylsilylacetylene (1.34 ml, 9.6 mmol, 2.1 when volume), stirred at room temperature for 1 hour. Extracted with ethyl acetate, the organic phase was washed with saturated brine, no over anhydrous sodium sulfate, and dried under reduced pressure to spin. Finally, to give a brown solid was purified by silica gel column 5-(trimethylsilylethynyl)-2-aminopyridine (867 mg, yield: 95%).

References:

CN105622638,2016,A Location in patent:Paragraph 0369