6-BROMO-3-METHYL-3H-IMIDAZO[4,5-B]PYRIDINE

Add 6-bromo-3-methyl-3H-imidazolyl (4, 5-b)pyridine (0.4 mmol) to an oven-dried 15 mL sealed tube equipped with a magnetic stir bar equipped with a magnetic stir bar.Sulfur powder (S8) (0.8 mmol), ethyl bromofluoroacetate (1.0 mmol), Under Na2S2O4 (0.8 mmol) as a catalyst, The solvent is a solution of 1, 2-dichloroethane (DCE) (2.0 mL) and the reaction is stirred at 80 C.Mix for 24 hours. After the reaction, The reaction mixture was cooled to room temperature and the mixture was extracted with dichloromethane.The combined organic layers were dried over anhydrous Na2SO4. Fast column chromatography using 300-400 mesh silica gel, The crude mixture was purified by (preparation of petroleum (PE): ethyl acetate (EA) = 10:1) by preparative TLC.The white solid product (I-43) was obtained, m.p.: 139.1 - 140.3 C, yield 53%.To a solution of 4-[(4-bromophenyl)methyl]-1 , 4-thiazinane 1, 1-dioxide 1-5 (303 mg, 1 .0mmol) in THF (2 mL)was added bis(triphenylphosphine)palladium dichloride (35 mg, 0.05mmol) and Cul (19 mg, 0.10 mmol), with nitrogen bubbling through the mixture. TEA (1.4 mL, 10 mmol), followed by trimethylsilylacetylene (200 pL, 1 .4 mmol) were added, still under bubbling of nitrogen. After 2 mm, the vial was sealed and the reaction was stirred for 18 h at 90C. The reaction mixture was diluted with DCM (10 mL) and washed withwater (10 mL) and brine (10 mL) before passing through a phase separator cartridge (Biotage). The solvent was removed in vacuo to give a residue which was was purified by flash column chromatography (Biotage Isolera Four, lOg KP-Sil column, 1% EtOAcI isohexane to 50% EtOAc I isohexane) to afford the title compound as a brown oil (50 mg, 0.16 mmol, 16%).:_Procedure similar to that described for 4-(4-trimethylsilanylethynyl-benzyl)-thiomorpholine-1, 1-dioxide 1-9, except To a solution of

Molecular Weight:212.05
XLogP3:1.4
Hydrogen Bond Acceptor Count:2
Exact Mass:210.97451
Monoisotopic Mass:210.97451
Topological Polar Surface Area:30.7
Heavy Atom Count:11
Complexity:153
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes