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

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Reaction Steps

Compound 4h was prepared following the procedure described in Step 3 of Example 1. Briefly described here, 65 mg (0.23 mmol) of 3-(5,6-dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one 3c, 11 mg (0.28 mmol) of 60% sodium hydride and 52 mg (0.28 mmol) of 2-bromomethyl-6-methyl-pyridine (prepared as described by Paine, J. B.; J. Het. Chem. 1987, 351) in 0.7 mL N,N-dimethylformamide were stirred at rt for 2 h. The product was purified using reverse phase HPLC, mobile phase with a gradient 10-70% acetonitrile in 50 min. HPLC fractions containing pure product 4h were lyophilized to give 41 mg of a white solid as trifluoroacetate salt: LC-MSD, m/z for C24H21N3O2 [M+H]+=384.5, HPLC retention time: 0.4 min; 1H NMR (400 MHz, CDCl3): δ 2.5 (s, 3H), 2.8 (s, 3H), 2.85 (s, 3H), 6.05 (s, 2H), 7.2-7.3 (m, 1H), 7.4-7.5 (m, 2H), 7.5-7.6 (m, 1H), 7.6-7.7 (m, 1H), 8.0-8.1 (m, 1H), 8.3-8.4 (m, 1H), 8.4 (s, 1H), 8.7 (s, 1H), 8.9 (s, 1H).

Provenance & Evidence