Boron tribromide → 7-Ethyl-5-({4-[(1E)-3-(4-methyl-1-piperazinyl)-3-oxo-1-propen-1-yl]phenyl}oxy)-6-phenyl-2-naphthalenol

Participants

Reaction Steps

To a solution of 1-[(2E)-3-(4-{[3-ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoyl]-4-methylpiperazine (61) (83 mg, 0.17 mmol) in reagent grade CH2Cl2 (8 mL) at −10° C. was added BBr3 (97 μL, 1.03 mmol) dropwise. The mixture was then stirred at 0° C. to 5° C. for 6 h, poured into saturated aqueous NaHCO3 (30 mL) and extracted with CH2Cl2. The combined extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as a brown solid. The crude product was triturated with hot hexanes (containing small amount of CH2Cl2 and MeOH) to give 44 mg (55%) of the title compound (63) as an off-white solid. mp 195-196° C. 1H NMR (400 MHz, CH3OH-d4): δ 1.07 (t, J=7.5 Hz, 3H), 2.31 (s, 3H), 2.47 (br s, 4H), 2.54 (q, J=7.5 Hz, 2H), 3.70 (br s, 4H), 6.54 (d, J=8.8 Hz, 2H), 6.91 (d, J=15.4 Hz, 1H), 6.96 (dd, J1=9.1 Hz, J2=2.4 Hz, 1H), 7.10-7.17 (m, 3H), 7.18-7.28 (m, 3H), 7.37 (d, J=8.6 Hz, 2H), 7.44 (d, J=15.4 Hz, 1H), 7.52 (s, 1H), 7.60 (d, J=9.1 Hz, 1H). LCMS (ESI): m/z 493 (M+H)+, m/z 491 (M−H)−. HRMS (EI) Calc for C32H32 N2O3: 493.2491 (M+•). Found: 493.2500.

Provenance & Evidence