4-Methoxybenzylamine → HCID 67404292, compound

Participants

Reaction Conditions

Reaction Steps

NaOtBu (68.23 mg, 0.71 mmol, 3.0 eq.), Xantphos (6.8 mg, 0.012 mmol, 5 mol %), Pd2 dba3 (10.8 mg, 0.012 mmol, 5 mol %) are added to a flask dried under vacuum. The reagents are dissolved in toluene distilled with CaH2 under argon (0.8 ml). The red solution is degassed under argon with sonication for 30 seconds. A solution of (Z)-1-bromo-2-(2-bromo-2-phenylvinyl)benzene (80 mg, 0.24 mmol, 1.0 eq) and p-methoxybenzyl amine (114 mg, 0.83 mmol, 3.5 eq.) in toluene distilled with CaH2 under argon (0.8 ml) is added to the catalytic system. After addition, the reaction medium is degassed with argon, and stirred for 1 hour 30 minutes at 55° C. Then, the reaction medium is degassed with carbon monoxide (in a flask, 1 atm.) for 25 minutes at 55° C. Then, the reaction medium is stirred at 90° C. for 16 hours. After cooling down to a.t., the reaction medium is quenched with a 1N HCl solution (5 ml). The organic phases are extracted with dichloromethane (twice), washed with a saturated solution of NaCl (twice), dried over MgSO4 then concentrated under reduced pressure. The crude is then purified by silica gel chromatography (pentane/diethyl ether (7/3)) in order to obtain 2-(4-methoxybenzyl)-3-phenylisoquinolin-1(2H)-one (45 mg, yield=54%) in the form of a yellowish solid.

Provenance & Evidence