2-Chloropyridine → HCID 25096016, compound

Participants

Reaction Conditions

Reaction Steps

The 2-chloro pyridine was converted the pyridone following the procedure of J. Am. Chem. Soc. 2006, 128, 1094-10695. To a solution of 1-chloro-N-[(1R)-2-methyl-1-(trifluoromethyl)propyl]pyrido[4,3-c]-1,6-naphthyridin-6-amine (1100 mg, 3.10 mmol) in dioxane (10 mL) and water (10 mL) was added KOH (696 mg, 12.4 mmol), 1-[2′-(di-tert-butylphosphino)-2,6-diisopropylbiphenyl-4-yl]ethyl (263 mg, 0.62 mmol) and Pd2 (dba)3 (284 mg, 0.31 mmol). The stirring solution was heated to 100° C. overnight. The reaction mixture was cooled and worked up with EtOAc and water. The organic layers were separated, dried with MgSO4, filtered, and concentrated by rotary evaporation. The oily residue was purified by silica gel column chromatography CH2Cl2 to MeOH 30% provided the 6-{[(1R)-2-methyl-1-(trifluoromethyl)propyl]amino}pyrido[4,3-c]-1,6-naphthyridin-1(2H)-one. 1H NMR (600 MHz, CD3OD) δ 11.30 (s, 1H), 9.05 (d, 1H), 8.95 (d, 1H), 7.62 (d, 1H), 6.80 (d, 1H), 5.48 (m, 1H), 2.40 (m, 1H), 1.17 (d, 3H), 1.10 (d, 3H). LRMS (ESI) calc'd for (C16H16F3N4O) [M+H]+, 337.1; found 337.1.

Provenance & Evidence