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

Participants

Reaction Steps

Experimental conditions analogous to those described for Step 3 of Example 1 were used with 120 mg (0.402 mmol) of 3-(3-Fluoro-4-methoxy-benzoyl)-1H-[1,5]naphthyridin-4-one, 121.1 mg (0.483 mmol) of 2-bromo-6-bromomethyl-pyridine, 19.3 mg (0.483 mmol, 60% dispersion in oil), and 2 mL of N,N dimethylformamide. 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 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3-fluoro-4-methoxy-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one. LC-MSD, m/z for C22H15BrFN3O3 [M+H]: 468.03.

Provenance & Evidence