6-(5,5-Dimethyl[1,3,2]dioxaborinan-2-yl)-2-fluorobenzonitrile → 5-(4-Fluorophenyl)-2-trifluoromethyl[1,8]naphthyridine

Participants

Reaction Steps

In the attempted coupling of trifluoromethanesulfonic acid 2-fluoro-5-(7-trifluoromethyl[1,8]naphthyridin-4-yl)phenyl ester (30.0 mg, 0.068 mmol) with a 1:1 mixture of 3-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-2-fluorobenzonitrile and 6-(5,5-dimethyl[1,3,2]dioxaborinan-2-yl)-2-fluorobenzonitrile (34.4 mg) following the procedure described in Example 35 part c), none of the expected product was obtained. Instead, the triflate was reduced, affording 5-(4-fluorophenyl)-2-trifluoromethyl[1,8]naphthyridine (13.9 mg, 42%). δH (360 MHz, CDCl3) 7.27-7.31 (2H, m), 7.46-7.50 (2H, m), 7.55 (1H, d, J 4.6), 7.82 (1H, d, J 8.4), 8.49 (1H, d, J 8.8), 9.27 (1H, d, J 4.6). m/z (ES+) 293 [MH]+.

Provenance & Evidence