2-ETHOXY-3-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PYRIDINE

A suspension of 3-bromo-2-ethoxypyridine (Preparation 1 1 , 28.69 g, 142.0 mmol), bis(pinacolato)diboron (43.3 g, 170.5 mmol), and potassium acetate (41 .8 g, 425.9 mmol) in DMSO (100 mL) was degassed with nitrogen and [1 , 1 '- bis(diphenylphosphinoferrocene]dichloro palladium (II) (5.8 g, 7.93 mmol) was added and the reaction mixture was stirred for 6 hours at 95 °C. The reaction mixture was filtered through a pad of Arbocel which was washed with ethyl acetate (500 mL). The filtrate was concentrated in vacuo and the crude material was purified by silica gel column chromatography eluting with 50percent ethyl acetate in cyclohexane to afford the title compound as a red oil (34.4g, 74percent). A suspension of 3-bromo-2-ethoxypyridine (Preparation 1 1 , 28.69 g, 142.0 mmol), bis(pinacolato)diboron (43.3 g, 170.5 mmol), and potassium acetate (41 .8 g, 425.9 mmol) in DMSO (100 mL) was degassed with nitrogen and [1 , 1 '- bis(diphenylphosphinoferrocene]dichloro palladium (II) (5.8 g, 7.93 mmol) was added and the reaction mixture was stirred for 6 hours at 95 °C. The reaction mixture was filtered through a pad of Arbocel which was washed with ethyl acetate (500 mL). The filtrate was concentrated in vacuo and the crude material was purified by silica gel column chromatography eluting with 50percent ethyl acetate in cyclohexane to afford the title compound as a red oil (34.4g, 74percent).

Molecular Weight:249.12
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:249.1536237
Monoisotopic Mass:249.1536237
Topological Polar Surface Area:40.6
Heavy Atom Count:18
Complexity:280
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes