Sodium hydride → HCID 16731095, compound

Participants

Reaction Steps

Compound 9a was prepared following the procedure outlined in Step 3 of Example 1. Briefly described here, 36 mg (0.13 mmol) of 3-(3,4-dimethyl-benzoyl)-1H-cinnolin-4-one 8a, 7 mg (0.17 mmol) of 60% sodium hydride and 33 mg (0.17 mmol) of 2-bromomethyl-6-methyl-pyridine in 0.7 mL N,N-dimethylformamide at rt for 3 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 lyophilized to give 34 mg of a pale yellow solid 9a as the trifluoroacetate salt: LC-MSD, m/z for C24H21N3O2 [M+H]+=384.5, HPLC retention time: 2.3 min; 1H NMR (400 MHz, CDCl3): δ 2.3 (s, 3H), 2.35 (s, 3H), 2.85 (s, 3H), 6.1 (s, 2H), 7.15-7.2 (m, 1H), 7.25-7.3 (m, 1H), 7.45-7.55 (m, 2H), 7.6-7.7 (m, 3H), 7.7-7.8 (m, 1H), 8.0-8.1 (m, 1H), 8.3-8.4 (m, 1H).

Provenance & Evidence