Triphenylphosphine → 1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-[2-(1-piperidinyl)ethoxy]-2(1H)-quinolinone

Participants

Reaction Conditions

Reaction Steps

To a solution of 10 mg of 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone (INTERMEDIATE 3) dissolved in 2 mL of anhydrous THF was added 87 mg of Ph3P and 43 mg of 1-piperidine ethanol. The resulting mixture was heated to 65° C. for 10 min. Then 72 mg of diisopropyl azodicarboxylate was added dropwise over 2 min and the mixture was stirred for 1 h at 65° C. The resulting reaction mixture was concentrated and purified by preparative thin-layer chromatography, eluting with 100% EtOAc, to yield 1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-[2-(1-piperidinyl)ethoxy]-2(1H)-quinolinone. Mass spectrum (ESI) 531.3 (M+1). 1H NMR (500 MHz, CDCl3): δ 1H NMR (500 MHz, CDCl3) δ 7.51 (d, J=8 Hz, 2H); 7.38 (t, J=8 Hz, 1H); 7.31 (q, J=6.5 Hz, 1H); 6.98 (m, 2H); 6.54 (s, 1H); 5.90 (s, 1H); 4.08 (s, 2H); 2.83 (m, 6H); 2.61 (s, 4H); 1.68 (s, 4H); 1.48 (s, 2H).

Provenance & Evidence