1,2-Diaminocyclohexane → 2-((3-fluorobenzyl)oxy)-6-(5-fluoropyridin-2-yl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

Participants

Reaction Conditions

Reaction Steps

2-((3-fluorobenzyl)oxy)-7,8-dihydro-1,6-naphthyridin-5(6H)-one (20 mg, 0.07 mmol) was dissolved into DMF (1 mL) and treated with 2-bromo-5-fluoropyridine (17 mg, 0.1 mmol), 1,2-diaminocyclohexane (4 mg, 0.04 mmol) and CuI (2 mg, 0.01 mmol). The reaction was stirred at 100° C. over 72 h and then poured onto 3M LiCl and EtOAc (5 mL each). The organic layers were dried over Na2SO4, concentrated and the residue purified RP-HPLC to give the compound, 2-((3-fluorobenzyl)oxy)-6-(5-fluoropyridin-2-yl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one. LC-MS (M+H)=368.1.

Provenance & Evidence