1-Chloro-4-(chloromethyl)benzene → 4-(4-Chlorobenzyloxy)-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-chloro-4-(chloromethyl)benzene (26.4 mg, 0.16 mmol), 4-hydroxy-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one Part C (50 mg, 0.16 mmol) and K2CO3 (67.9 mg, 0.49 mmol) in DMF (1.0 mL) was stirred at 100° C. for 90 min The mixture was cooled to RT, filtered and the filtrate was concentrated. The crude product was purified by prep-HPLC (C18 column/Water:MeOH:TFA 90:10:0.1 to 10:90:0.1 gradient) yielding the title compound D-2-4-(4-chlorobenzyloxy)-1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)pyridin-2(1H)-one D-2 (30 mg, 41.2% yield) as white solid. LC/MS 430 (M+H)+, tR 0.93 min (method 5); 1H NMR (400 MHz, Chloroform-D) δ ppm 7.32-7.44 (4H, m), 7.24-7.28 (1H, m), 6.96 (1H, d, J=8.53 Hz), 6.80-6.91 (2H, m), 6.06-6.18 (2H, m), 5.03 (2H, s), 3.85 (5H, d, J=1.76 Hz), 1.35 (6H, s).

Provenance & Evidence