N-methyl-2-pyrrolidone → 3-((Trimethylsilyl)ethynyl)pyridin-2-amine

Participants

Reaction Steps

To a mixture of 3-iodo-pyridin-2-ylamine (40 g) described in Manufacturing Example 1-2-3, trimethylsilylacetylene (52 mL), copper(I) iodide (3.5 g), N,N-diisopropylethylamine (64 mL), and NMP (200 mL) was added tetrakis(triphenylphosphine)palladium(0) (10 g), which was stirred for 3 hours and 10 minutes at room temperature under a nitrogen atmosphere. Water was added to the reaction solution, which was then extracted with ethyl acetate 4 times. The solvent was evaporated under a reduced pressure, and the residue was purified by NH silica gel chromatography (heptane:ethyl acetate=4:1). The solution thus obtained was concentrated under a reduced pressure, and the residue was purified by silica gel chromatography (heptane:ethyl acetate=2:1, then 1:1) to obtain the titled compound (28 g).

Provenance & Evidence