Sodium hydride → HCID 16731172, compound

Participants

Reaction Steps

Compound 4i was prepared following the procedure outlined in Step 3 of Example 1. Briefly described here, 32 mg (0.12 mmol) of 3-(5,6-dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one 3d, 6 mg (0.14 mmol) of 60% sodium hydride and 26 mg (0.14 mmol) of 2-fluorobenzyl bromide were combined in 0.5 mL N,N-dimethylformamide and 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. The HPLC fractions containing pure product were lyophilized to give 43 mg of a pale yellow solid 4i as trifluoroacetate salt: LC-MSD, m/z for C24H19FN2O2 [M+H]+=387.5, HPLC retention time: 1.8 min; 1H NMR (400 MHz, CDCl3): δ 2.5 (s, 3H), 2.8 (s, 3H), 5.7 (s, 2H), 7.1-7.2 (m, 3H), 7.3-7.4 (m, 1H), 7.5-7.6 (m, 1H), 7.6-7.7 (m, 1H), 7.7-7.8 (m, 1H), 8.1-8.2 (m, 1H), 8.5-8.6 (m, 1H), 9.05 (s, 1H).

Provenance & Evidence