5-bromothieno[2,3-b]pyridine synthesis

Yield: 53%

Reaction Conditions:

with copper(ll) bromide;isopentyl nitrite in acetonitrile at 20;

Steps:

16.E 5-Bromothieno[2,3-b]pyridine
Example 16E 5-Bromothieno[2,3-b]pyridine The product of Example 16D (1.35 g. 9.0 mmol) was treated with iso-amylnitrite (Aldrich. 2.10 g. 18.0 mmol) and CuBr₂ (Aldrich, 4.03 g. 18.0 mmol) in MeCN (20 mL) at ambient temperature overnight. The reaction mixture was quenched with saturated NH₄Cl (20 mL) and then extracted with EtOAc (3*50 mL). The combined extracts were washed with brine (2*30 mL) and concentrated. The residue was purified with chromatography (SiO₂, EtOAc/hexane, v. 80/20. R^f=0.80) to give the title compound (1.03 g, yield, 53.0%). ¹H NMR (300 MHz, CDCl₃) 8 ppm 7.22 (d, J=6.10 Hz, 1H), 7.58 (d, J=6.10 Hz, 1H). 8.21 (d, J=2.37 Hz, 1H), 8.61 (d, J=2.0(3 Hz, 1H):MS (DCI/NH₃) m/z 214 (M+1)⁺, 216 (M+1)⁺.

References:

Abbott Laboratories US2008/153860, 2008, A1 Location in patent:Page/Page column 25