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With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 19h;Reflux; Inert atmosphere;
Step 2: Synthesis of 2-(tert-butyl)-6-aminophenanthridine 35.7 g (190 mmol) <strong>[172732-52-4]2-(1,3,2-dioxaborinan-2-yl)benzonitrile</strong>, 31.9 g (158 mmol) 2-bromo-4-(tertbutyl)aniline, 3.6 g (3.16 mmol) tetrakis(triphenylphosphine) palladium(0) and 59.0 g (427 mmol) K2CO3 were heated to reflux in a 2 L flask containing 400 ml toluene and 300 mL ethanol. The reaction mixture was heated for 19 hours under constant N2 purge. HPLC of the reaction mixture indicated consumption of the starting aniline. The mixture was cooled and then filtered to remove the base. The base was washed with EtOAc to remove trace organic. The combined filtrate was evaporated down to give impure oil. The oil was purified on a column of silica using 95/5/0.05 CH2Cl2/MeOH/NH4OH as eluent to obtain separation. The product fractions were evaporated of solvent and the resultant residue recrystallized from CH2Cl2/hexanes to yield 14.0 g of the target compound as white solids (35.5percent yield, confirmed by GC-MS).
35.5%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 19h;Reflux; Inert atmosphere;
Step 2: Synthesis of 2-(t-butyl)-6-amino-phenanthridine 35.7 g (190 mmol) 2- (1,3,2- I-dioxa barley-2-yl) benzonitrile, 31.9 g (158 mmol) 2- bromo -4- (t- butyl) aniline, 3.6g ( 3.16 mmol), tetrakis (triphenyl a) palladium (0) and 59.0 g (427 mmol) K2CO3, and toluene was heated to reflux at 400 2 ? flask containing 300 ethanol. The reaction mixture was heated under a constant N2 washed for 19 hours. HPLC of the reaction mixture indicates the consumption of the starting aniline. The mixture was cooled, and the base was removed by filtration. The base was washed with EtOAc to remove traces of organic matter. The combined filtrate was distilled to give the impure oil. Purification using a 95/5 / 0.05 CH2Cl2 / MeOH / NH4OH as eluent to give an oil on a silica column to remove. Evaporation of the solvent and the product fractions, the resulting residue was recrystallized from CH2Cl2 / hexane to give the (also identified with 35.5percent yield, GC-MS) 14.0 g of the target compound as a white solid.
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