sodium hydroxide; water; hydrogen bromide; ethyl acetate; copper(i) bromide
reactants are commercially availlable.
wyeth, us2003/32645, a1, (2003) step 5 8-bromo-6-methoxyquinoline to 5.05 g (29.0 mmol) 6-methoxy-quinolin-8-yl-amine in 25 ml of 48 percent hbr at 0°c. is added a solution of 2.60 g (37.7 mmol) and 20 ml h2o. after stirring at 0°c . for 15 min, the resulting mixture is added dropwise to a 75°c. solution of 5.0 g (34.8 mmol) cubr and 60 ml of 48percent hbr. after 5.5 h, the reaction mixture is neutralized with 150 ml of ice col d 5n naoh, the resulting mixture is stirred with 300 ml etoac and filtered through a pad of celite. this mixture is extracted 2*100 ml etoac, and the combined organics are washed with 1*200 ml h2o, 1* 200 ml brine, dried over na2so4, filtered, and the volatiles are evaporated. flash chromatography on sio2 gel, eluding with hexanes/etoac (4/1 to 1/1), gives 4.23 g (17.8 mmol, a 61percent yield) of t he title compound as a brown oil. ms (es) m/z 239 (mh) .
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