Sodium Bicarbonate → 1-{2-[4-({[5-bromo-6-(hydroxymethyl)-3-pyridinyl]methyl}amino)-1-piperidinyl]ethyl}-7-fluoro-1,5-naphthyridin-2(1H)-one

Participants

Reaction Steps

A mixture of 1-[2-(4-amino-1-piperidinyl)ethyl]-7-fluoro-1,5-naphthyridin-2(1H)-one (Intermediate 21: 50.9 mg, 0.175 mmol) and 5-bromo-6-(hydroxymethyl)-3-pyridinecarbaldehyde (Intermediate 40: 37.9 mg, 0.175 mmol) in DCE (3 ml) was stirred under N2 at room temperature overnight. Then, sodium triacetoxyborohydride (112 mg, 0.526 mmol) was added and the mixture was stirred for 8 h at RT overnight. Saturated NaHCO3 was added and the aqueous phase was extracted twice with DCM. The combined organic phases were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by Flash-Master chromatography on a 2 g silica gel cartridge using DCM/MeOH 9/1 as eluent to give 1-{2-[4-({[5-bromo-6-(hydroxymethyl)-3-pyridinyl]methyl}amino)-1-piperidinyl]ethyl}-7-fluoro-1,5-naphthyridin-2(1H)-one (21.5 mg, 25%) as a white solid.

Provenance & Evidence