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With dibenzo-18-crown-6; potassium acetate; copper; In N,N-dimethyl-formamide; at 120℃; for 4h;
General procedure: 2-aminobenzamide (1.4g, 0.010mol) in dibromochloromethane (2.1g, 0.010mol) dibenzo-18-crown-6 (1.1g, 0.0030mol), copper (2) (1.2g, 0.020mol), potassium acetate (2.8 g, 0.020mol), into a DMF in 100ml was reacted with stirring for 4 hours at 120 C. After the reaction cooled to H20: After layer separation the MC column purification (n-Hexane: MC) to yield the intermediate 1-1 1.1g (62% yield). Intermediate 1-8 (2.1g, 0.010mol) put in bromobenzene (1.6g, 0.010mol), by synthesis by the same method used in preparation Example 1-1 to give <Intermediate 1-9> 2.3g (yield 77%).
74%
With trifluoroacetic acid; In dichloromethane; at 20℃; for 0.5h;Inert atmosphere;
General procedure: 9 g (29.92 mmol) of Intermediate 1b and 50 mL of trifluoroacetic acid were dissolved in 80 mL of dichloromethane under nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 30 minutes. After completion of the reaction, the reaction solution was neutralized with anhydrous MgSO4, filtered, and concentrated. The concentrated solution was recrystallized from dichloromethane and methanol, thus obtaining 6.8 g of Intermediate 1c (yield: 68%).
6
[ 867248-91-7 ]
[ 18628-07-4 ]
Yield
Reaction Conditions
Operation in experiment
86%
With water; sodium hydroxide; In tetrahydrofuran; methanol; at 80℃; for 24h;
To a solution of 9-tosyl-9H-3,9'- bicarbazole or IC-2 (8.6 g, 17.6 mmol) in THF (150 mL) and methanol (60 mL), was added sodium hydroxide aqueous solution (10 g in 60 mL water). The mixture was heated at 80 C for 24 hours on a hot plate with a silicone oil bath. The resulting mixture was mixed with ethyl acetate and rinsed with brine, then loaded on silica gel (Grade 135) and purified by flash chromatography using eluents of ethyl acetate/hexanes (0% to 10%). After removal of solvents, the product was then collected to yield a white solid (Compound OSC-6) (5.0 g, in 86% yield). Confirmed by 1 HNMR.
77.9%
With potassium hydroxide; In tetrahydrofuran; ethanol; for 6h;Reflux;
d) 10.6 g (160.3 mmol) KOH 85% are dissolved in 450 ml EtOH, then 39.0 g (80.1 mmol) 3-Carbazol-9-yl-9-(p-tolylsulfonyl)carbazole dissolved in 180 ml THF are added and the clear solution is heated to reflux for 6 hours. The reaction mixture is cooled to RT and then added drop by drop to 1 l H2O. The resulting suspension is filtered and the residue is washed four times with H2O (200 ml each) and then dried at 80 C./125 mbar overnight to yield 25.6 g (96.1% of theory) of an off white solid. The crude product is suspended in 150 ml MeOH and heated to reflux for 2 hours. The suspension is cooled to RT and then to 0 C., filtered, washed twice with cold MeOH (20 ml each) and dried at 60 C./125 mbar overnight to yield 23.4 g (87.9%) of an off white solid. This procedure is repeated twice to yield 20.76 g (77.9% of theory) 3-Carbazol-9-yl-9H-carbazole as a white solid. 1H-NMR (400 MHz, CDCl3): delta 8.35-8.20 (m, 3H), 8.16 (br s, 1H), 8.08 (d, J=7.6 Hz, 1H), 7.64-7.28 (m, 11H).
With sodium hydroxide; In tetrahydrofuran; methanol; water;
Step 4. 3-(9-carbazolyl)-9-tosylcarbazole (10.0 g, 21 mmol), NaOH (8.0 g, 200 mmol), 80 mL of THF, 40 mL of MeOH and 40 mL of water were added to a 500 mL round flask. The reaction was heated to reflux for 12 hours. After cooling, the mixture was purified by a silica gel column. The yield of 3-(9-carbazolyl)carbazole was 8 g.
3 g
With potassium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 4h;
Intermediate 5-2 (12 g), potassium hydroxide (1.0 g), tetrahydrofuran (36 ml) and methanol (18 ml) were added to a 100 ml three-necked round bottom flask and stirred at room temperature for 4 hours. Silica gel filtration and concentration under reduced pressure. The solid phase was washed with water and then recrystallized from dichloroethane to obtain 3 g of the title compound
3 g
With sodium hydride; In tetrahydrofuran; methanol; at 20℃; for 4h;
12 g of Intermediate 5-2, 1.0 g of sodium hydride, 36 mL of tetrahydrofuran and 18 mL of methanol were added to a 100 mL three-neck round bottom flask, and the mixture was stirred at room temperature for 4 hours. After silica gel filtration, the filtrate was concentrated under reduced pressure. The solid was washed with water and recrystallized from dichloroethane to give 3 g of the title compound.
3 g
With potassium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 4h;
In a 100 mL three-necked round bottom flask, intermediate 5-2 (12 g), potassium hydroxide (1.0 g), tetrahydrofuran (36 mL) and methanol (18 mL) were added and stirred at room temperature for 4 hours. The silica gel filter is then concentrated under reduced pressure. The solid phase was washed with water and then recrystallized with dichloroloethane to give 3 g of the title compound.
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