Sodium hydride → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-7-methyl-1H-[1,8]naphthyridin-4-one

Participants

Reaction Steps

Experimental conditions analogous to those described for Step 3 of Example 1 were used with 0.100 g (0.342 mmol) of 3-(3,4-Dimethyl-benzoyl)-7-methyl-1H-[1,8]naphthyridin-4-one, 16.4 mg (0.410 mmol, 60% dispersion in oil) of sodium hydride, 0.103 g (0.410 mmol) of 2-bromo-6-bromomethyl-pyridine and 3.5 mL of N,N dimethylformamide. The crude brown solid was purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA to yield 29.5 mg of 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-7-methyl-1H-[1,8]naphthyridin-4-one as an off white solid. LC-MSD, m/z for C24H20BrN3O2 [M+H]: 463.07 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.7 min

Provenance & Evidence