2-Bromo-3-fluoropyridine → 3-Fluoro-2-(2-fluoro-5-nitrophenyl)pyridine

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Reaction Steps

2-Bromo-3-fluoropyridine, prepared according to the procedure of Queguiner et al. in Tetrahedron, 1983, 39, 2009-21, was coupled with 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (as prepared in Example 2, part a)) by the method of Example 2, part b) to yield 3-fluoro-2-(2-fluoro-5-nitrophenyl)pyridine, which was transformed into 2-(5-bromo-2-fluorophenyl)-3-fluoropyridine by the method of Example 4, parts b) and c). This was converted into 4-fluoro-3-(3-fluoropyridin-2-yl)phenylboronic acid by the method of Example 5 part d), using bis(neopentyl glycolato)diboron instead of bis(pinacolato)diboron. δH (400 MHz, DMSO) 8.58 (1H, m), 8.19 (2H, s), 8.04 (1H, dd, J 8 and 2), 7.95 (1H, m), 7.86 (1H, m), 7.57 (1H, m), 7.31 (1H, dd, J 11 and 8).

Provenance & Evidence