5-CHLOROTHIENO[3,2-B]PYRIDINE

10b) 5-Chlorothieno [3, 2-b] pyridine A. 5-Chlorothieno[3, 2-b]pyridine The title compound is prepared from 3-acetyl thiophene according to the procedure described in J. Chem. Soc., Perkin Trans. I, 1981, 1531. The crude product is purified by column chromatography eluding with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes to afford a white solid. 1 H NMR (CDCl3, 300 MHz) delta 8.12 (d, 1H), 7.80 (d, 1H), 7.51 (d, 1H), 7.28 (d, 1H), EI MS, [M]+ =169, 171, Cl pattern.A. 5-Chlorothieno[3, 2-b]pyridine The title compound is prepared from 3-acetyl thiophene according to the procedure described in J. Chem. Soc., Perkin Trans. I, 1981, 1531. The crude product is purified by column chromatography eluding with a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes to afford a white solid. 1 H NMR (CDCl3, 300 MHz) delta8.12 (d, 1H), 7.80 (d, 1H), 7.51 (d, 1H), 7.28 (d, 1H), EI MS, [M]+ =169, 171, Cl pattern.(A) A mixture of 1019 A solution of commercially available 5-chlorothieno[3, 2-D]pyridine (0.600 g, 3.537 mmol) in tetrahydrofuran (15 mL) was cooled to -78 C. Then a 2.5 M solution of n-butyl-lithium in hexane (3.3 mL, 5.305 mmol) was added at -78 C. The temperature was allowed to raise to -40C and the mixture was stirred for 30 minutes. The mixture was cooled to -78 C and bromine (0.362 mL, 7 07 mmol) was added dropwise. The mixture was stirred at -78C for 1 hour and the reaction mixture was quenched with 50 mL of water. The aqueous mixture was extracted with ethyl acetate (3 * 50 mL), the combined organic layers were dried over Na2S04 and concentrated. The residue was purified by chromatography on HP-Sil SNAP cartridges using a Biotage Isolera One purification system employing an ethyl acetate/n- heptane gradient (0/100 -> 10/90) to afford the title compound (0.774 g, 88 %).1H-NMR (400 MHz, DMSO-d6) oe 8.52 (d, IH), 7.80 (s, IH), 7.50 (d, 1H). MS (ESl); m/z = 249.91 [M+H]+

Molecular Weight:169.63
XLogP3:2.9
Hydrogen Bond Acceptor Count:2
Exact Mass:168.9752980
Monoisotopic Mass:168.9752980
Topological Polar Surface Area:41.1
Heavy Atom Count:10
Complexity:131
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes