Sodium hydride → 1-(6-bromo-pyridin-2-ylmethyl)-3-(5,6-dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one

Participants

Reaction Steps

Compound 4ww was prepared following the procedure described in Step 3 of Example using 45 mg (0.16 mmol) of 3-(5,6-dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one 3d, 8 mg (0.21 mmol) of 60% sodium hydride and 53 mg (0.21 mmol) of 2-bromo-6-bromomethyl-pyridine in 0.7 mL N,N-dimethylformamide and stirring the reaction mixture at rt for 2 h. The product was purified using reverse phase HPLC (mobile phase with a gradient 10-50% acetonitrile in 50 min). The HPLC fractions containing pure product were combined, evaporated under vacuum and neutralized using methanolic ammonia and purified by flash chromatography (using 30-100% ethyl acetate in hexane) to give 18 mg of a pale yellow solid: LC-MSD, m/z for C23H18BrN3O2 [M+H]+: 448.4, 450.4; Reverse phase HPLC gradient, 20-95% acetonitrile with 0.1% TFA in 4 minutes, retention time=2.1 min; 1H NMR (400 MHz, CDCl3): δ 2.35 (s, 3H), 2.5 (s, 3H), 5.5 (s, 2H), 7.0-7.1 (m, 1H), 7.3-7.35 (m, 1H), 7.35-7.4 (m, 1H), 7.4-7.6 (m, 4H), 7.6-7.7 (m, 1H), 8.4-8.45 (m, 1H), 8.5 (s, 1H).

Provenance & Evidence