Triphenylphosphine → HCID 10302036, compound

Participants

Reaction Steps

Diethyl azodicarboxylate (50 μL, 0.32 mmol) was added dropwise to a solution of 1-(2,6dichlorophenyl)-5-(2-chlorophenyl)-7-hydroxy-3,4-dihydro-2(1H)-quinazolinone (30 mg, 0.07 mmol) INTERMEDIATE 49), triphenylphosphine (95 mg, 0.36 mmol) and 1-(2-hydroxyethyl)piperidine (55 mg, 0.43 mmol) in 1 mL tetrahydrofuran at 65° C. under an argon atmosphere. After 1 h the solution was cooled to RT and partitioned between saturated NaHCO3 (5 mL) and EtOAc (15 mL). The organic phase was separated, dried over Na2SO4, filtered and concentrated. The residue was purified by thin layer chromatography using EtOAc followed by CHCl3/MeOH/NH4OH (87/12/1) as the eluent to give 1-(2,6-dichlorophenyl)-5-(2-chlorophenyl)-7-[2-(1-piperidinyl)ethoxy]-3,4-dihydro-2(1H)-quinazolinone. 1H NMR(CDCl3, 500 MHz): δ 1.44 (m, 2H), 1.62 (m, 4H), 2.48 (m, 4H), 2.72 (m, 2H), 4.00 (t, 2H, J=6.0 Hz), 4.18 (d, 1H, J=14.0 Hz), 4.36 (d, 1H, J-14.0 Hz), 5.22 (s, 1H), 5.76 (d, 1H, J=1.8 Hz), 6.45 (d, 1H, J=2.0 Hz), 7.28-7.39 (m, 4H), 7.45-7.53 (m, 3H). MS(ES) 530 (M+H); LC 1: 2.28 min.

Provenance & Evidence