2-Bromo-6-(bromomethyl)pyridine → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-1H-[1,5]naphthyridin-4-one

Participants

Reaction Steps

Experimental conditions analogous to those described for Step 1 of Example 2 using 75 mg (0.255 mmol) of 3-(4-Methoxy-3-methyl-benzoyl)-1H-[1,5]naphthyridin-4-one, 76.8 mg (0.306 mmol) of 2-bromo-6-bromomethyl-pyridine, 0.61 mL (0.306 mmol, 0.5 M in toluene) of potassium hexamethyldisilazane, and 2.5 mL of THF. The crude product was purified by flash column chromatography using a gradient of 20-100% ethyl acetate in hexane and further purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA to yield 20 mg of 1-(6-Bromo-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-1H-[1,5]naphthyridin-4-one. LC-MSD, m/z for C23H18BrN3O3 [M+H]: 464.05 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.0 min.

Provenance & Evidence