Sodium hydride → 3-(5,6-Dimethyl-pyridine-3-carbonyl)-1-(2-fluoro-benzyl)-1H-quinolin-4-one

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Reaction Steps

Compound 4g was prepared following the procedure described in Step 3 of Example 1. 63 mg (0.23 mmol) of 3-(5,6-dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one 3c, 11 mg (0.27 mmol) of 60% sodium hydride and 51 mg (0.27 mmol) of 2-fluorobenzyl bromide were combined in 1 mL N,N-dimethylformamide at rt for 1 h. The product was purified using reverse phase HPLC, mobile phase with a gradient 10-70% acetonitrile in 50 min. The HPLC fractions containing pure product were combined and the combined solutions was lyophilized with 1 mL of 1 M HCl to give 82 mg of a pale yellow solid 4g as its HCl salt: LC-MSD, m/z for C24H19FN2O2 [M+H]+=387.5, HPLC retention time: 1.2 min; 1H NMR (400 MHz, CDCl3): δ 2.55 (s, 3H), 2.9 (s, 3H), 5.55 (s, 2H), 7.05-7.2 (m, 3H), 7.3-7.4 (m, 1H), 7.45-7.55 (m, 2H), 7.65-7.75 (m, 1H), 8.35-8.45 (m, 2H), 8.6 (s, 1H), 8.85 (s, 1H).

Provenance & Evidence