Indolo[3,2-b]carbazole

A solution of 25.0 g (101.5 mmol) of 3, 3-methylenediindole and 15.1 g (101.5 mmol) of triethyl orthoformate in 400 ml of methanol was added with 1.4 ml of concentrated sulfuric acid and stirred for 5 h while refluxing under heating. The reaction solution was cooled in an iced water bath. The precipitate was collected by filtration and washed with 500 ml of methanol, to obtain 19.0 g of brown solid, which was identified as the following intermediate 2-2 by FD-MS analysis (yield: 73percent).In a 2000-ml three-necked flask that had been deaerated and filled with nitrogen were placed 50.69 g (0.2058 mole) of 3, 3'-methylenediindole and 30.55 g (0.2061 mole) of triethyl orthoformate, then 640 g of methanol was added, and the mixture was stirred. To the mixture was added dropwise 5.0 g (0.0515 mole) of concentrated sulfuric over 3 minutes and the mixture was heated under reflux for 1 hour. The mixture was cooled to room temperature and the reddish brown crystals formed were collected by filtration and reslurried twice with 500 ml of methanol. The solvent was distilled off under reduced pressure and 36.81 g of solid C or indolo[3, 2-b]carbazole (0.1438 mole, 69.9 percent yield) was obtained as a reddish brown powder.Concentrated HCl (0.25 mL) was added to a solution of malassezin (0.75 g) in tetrahydrofuran (120 mL) at ambient temperature. The resulting mixture was heated to reflux overnight. After the reaction was complete (monitored by TLC using 40percent ethyl acetate/hexanes). The reaction mixture was cooled to ambient temperature and stirred for 1 hr. Filtered the solid, washed with tetrahydrofuran (20 mL) and dried to give Indolo[3, 2-b]carbazole (CV-8685) light yellow solid (0.55 g, 78percent). (0220) HPLC purity: 96.22percent (area percent). Synthesis of Compound B; 34.9 g (0.31 mole) of 1, 4-cyclohexanedione, 90 g (0.62 mol) of phenylhydrazin-HCl, and 1 mL of acetic acid were put into a 1L one-neck round flask, and 600 mL of ethanol was added thereto. The resulting mixture was heated at 50 °C for 1 hour, and was cooled to room temperature. The resulting solid was filtered, was washed several times with ethanol, and was dried in a vacuum to collect 73 g of pink Compound A with a yield of 80percent. 600 mL of acetic acid and 120 mL of sulfuric acid were put into a 5L one-neck round flask, and were cooled in an ice bath. 217.5 g (0.74mole) of Compound A was added to the resulting mixture, and was strongly stirred at 0 °C for 10 minutes. The ice bath was removed, and the resulting mixture was stirred at room temperature for 10 minutes. The resulting mixture was heated by a heating mantle. The heating was stopped at a temperature of about 45 °C, and the resulting mixture was stirred. When the resulting mixture was stable, the resulting mixture was slowly cooled to room temperature, and was stirred at room temperature. The resulting solid was filtered, was washed with acetic acid, water, and ethyl ether in this order, and was dried in a vacuum to collect 51 g of Compound B with a yield 26.7percent. Compound 1 was synthesized according to this reference.10 40 mL of AcOH and 8 mL of concentrated H2SO4 were added into a round-bottom flask in an ice bath. Cyclohexane-1, 4-dione bis(phenylhydrazone)(8.80 g, 30 mmol) was added dropwise. After that, thetemperature was warmed up to 30 As shown in Fig. 24R, to a solution of C O (39 g, 0.39 mol, 20.0 eq) in H20 (58 mL) was slowly added a solution of compound 1 (5.0 g, 19.53 mmol, 1.0 eq) in AcOH (58 mL) at -5C. The mixture was stirred at 0- 5C for 2 h. TLC analysis of the reaction mixture showed full conversion to the desired product. The mixture was filtered and the filter cake was washed with EtOH and H20. Then the mixture was filtered to afford impure compound 2 (1.652 g, 29%).

Molecular Weight:256.3
XLogP3:5.2
Hydrogen Bond Donor Count:2
Exact Mass:256.100048391
Monoisotopic Mass:256.100048391
Topological Polar Surface Area:31.6
Heavy Atom Count:20
Complexity:346
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes