Sodium Carbonate → 7-Fluoro-8-methyl-2-(pyridin-3-yl)quinoline-3-carbaldehyde

Participants

Reaction Steps

Prepared according to the procedure described for Intermediate 1, utilising 2-chloro-7-fluoro-8-methylquinoline-3-carbaldehyde (5.0 g, 22.36 mmol), 3-pyridylboronic acid (3.02 g, 24.6 mmol), tetrakis(triphenylphosphine)palladium(0) (127 mg, 0.11 mmol) and Na2CO3 (3.55 g, 33.54 mmol) in water (30 mL) and DME (60 mL). The title compound (5.52 g, 93%) was obtained as a beige solid. δH (DMSO-d6) 10.13 (s, 1H), 9.08 (s, 1H), 8.95 (dd, J 2.3, 0.8 Hz, 1H), 8.75 (dd, J 4.9, 1.7 Hz, 1H), 8.24 (dd, J 9.0, 6.4 Hz, 1H), 8.16-8.21 (m, 1H), 7.68 (t, J 9.2 Hz, 1H), 7.61 (ddd, J 7.9, 4.0, 0.8 Hz, 1H), 2.66 (d, J 2.4 Hz, 3H). LCMS (ES+) 267 (M+H)+, RT 2.16 minutes.

Provenance & Evidence