3-Iodocarbazole

As an example of a material according to the invention, a synthetic method of a compound represented by formula (73) 9-{4-[3-(N, N-diphenylamino) -N-carbazolyl] phenyl} -10-phenylanthracene (hereinafter referred to as CzAlPA) below will be described. Note that, 9-phenyl-10-(4-bromophenyl) anthracene is prepared in the manner shown in Example 1. [0230][0231]First, a synthetic method of 3-iodocarbazole will be shown below. 4.5 g (20 EPO [Example 1]; [0199] A synthesis method of a compound represented by the following structural EPO To a solution of 9H-carbazole (500 mg, 2.99 mmol) in acetic acid (15 mL) was added N-iodosuccinimide (740 mg, 3.29 mmol) and the reaction mixture was stirred at room temperature for 1 h. The mixture was evaporated and the residue was neutralized by addition of 10percent aqueous potassium carbonate, and the resulting solid was collected. The crude product was purified by column chromatography eluting with hexane:ethyl acetate (33: 1) to give the title compound (750 mg, 2.56 mmol, 86percent) as a pale yellow oil. LCMS: 81percent, Rt 1.900, ESMS m/z 292 (M-H)Potassium iodide (2.3 g, 0.020 mol) and 50 mL of glacial acetic acid were placed in a 100 mL round-bottomed flask; the reaction was carried out using a mixture of potassium carbonate (2.5 g, 0.015 mol), potassium iodate (2.5 g, 0.0115 mol) The mixture was cooled and filtered through a Buchner funnel to give a solid crude product which was washed with 200 mL of a solution of 5percent (wtpercent) NaHSOj (wtpercent) in water, and the reaction was stirred at 80 ° C water bath until the color of the resulting iodine disappeared (about 5 h) The crude product was dried, recrystallized from ethanol / THF, decolorized with a small amount of activated charcoal, and finally a white crystal was obtained (6.4 g; yield: 72percent).Synthesis of 3-iodo-9H-carbazole. To a solution of 9H-carbazole (5.57g, 33.3 mmol) and KI (3.68g, 22.2 mmol) in AcOH (92 mL) was heated to 100 °C for 1 h. KI0Carbazole (Compound 1, 4.0 g, 23.6 mmol) was dissolved in ethanol (800 mL) in a 1-L three-necked flask, and then iodine (3.0 g) and NaIOCarbazole 1 (16.7 g, 101mmol) was dissolved in boiling glacial acetic acid (250 mL), and KI (11.73 g, 135mmol) was added. The solution was cooled, ground potassium iodate (23.42 g, 150mmol) was added, and the mixture was boiled until it acquired a clear strawcoloredtint (10 min).The hot solution was decanted fromtheundissolved potassium iodate, and it was allowed to cool to45°C. The faintly brown plates were rapidly filtered off andrecrystallized from alcohol, and the solution was allowed tocool to 45°C. The faintly brown plates were rapidly filtered offand recrystallized from ethanol; the solution was allowed tocool to 45°Candfiltered, yielding 9.73 g (47percent) of 5 as a brownsolid; mp 202°C (mplit. 202°C), 1H NMR (600MHz, CDCl3) δppm 8.41 (s, 1 H), 8.11 (br. s., 1 H), 8.04 (d, J = 7.70 Hz, 1 H), 7.68 (dd, J = 8.53, 1.74Hz, 1 H), 7.42–7.49 (m, 2 H), 7.22–7.28 (m, 2 H); 13C NMR (100MHz, CDCl3) δ ppm 139.5, 138.6, 134.1, 129.2, 126.6, 125.9, 122.1, 120.5, 119.9, 112.6, 110.7.Maldi-Tof MS: m/z calcd for [Ma) 76.9 g (0.460 mo) carbazoe and 104 g (0.460 mo) 1iodopyrroNdine2, 5dione (NS) in lOOm m acetic acid are stirred under nitrogen at 20 °C. After 5 h the product is filtered off. The product is crystailzed from 900 m ethano using 2 g charcoaL The ethano soution is filtered hot. The ethano soution is cooed to 20 °C and the product is filtered off (yied: 59.5g (44 percent)).76.9 g (0.460 mol) carbazole and 104 g (0.460 mol) 1-iodopyrrolidine-2, 5-dione (NIS) in 100m ml acetic acid are stirred under nitrogen at 20 °C. After 5 h the product is filtered off and crystalized from 900 ml ethanol using 2 g charcoal. The ethanol solution is filtered hot and cooled to 20 °C. The product is filtered off (yield: 59.5 g (44 percent)).Synthesis )benzimidazolo[1 , 2-a]benzimidazole a) 76.9 g (0.460 mol) of carbazole and 104 g (0.460 mol) of 1-iodopyrrolidine-2, 5-dione (NIS) in 100m ml of acetic acid are stirred under nitrogen at 20 °C. After 5 h the product is filtered off. The product is dissolved in 900 ml of ethanol at reflux, then 2 g of charcoal are added. The ethanol solution is filtered hot and cooled to 20 °C. The product is filtered off to yield 59.5 g (44 percent) of 3-iodo-9H-carbazole.a) 76.9 g (0.460 mol) carbazole and 104 g (0.460 mol) 1-iodopyrrolidine-2, 5-dione (NIS) in 100m ml acetic acid are stirred under nitrogen at 20 °C. After 5 h the product is filtered off. The product is crystalized from 900 ml ethanol using 2 g charcoal. The ethanol solution is filtered hot. The ethanol solution is cooled to 20 °C and the product is filtered off (yield: 59.5 (44 percent)).a) 76.9 g (0.460 mol) carbazole and 104 g (0.460 mol) 1-iodopyrrolidine-2, 5-dione (N IS) in1 00m ml acetic acid are stirred under nitrogen at 20 00. After 5 h the product is filtered off. The product is crystalized from 900 ml ethanol using 2 g charcoal. The ethanol solution is filtered hot. The ethanol solution is cooled to 20 00 and the product is filtered off (yield: 59.5 g (44 percent)).b) 76.9 g (0.460 mol) carbazole and 104 g (0.460 mol) 1-iodopyrrolidine-2, 5-dione (NIS) in 100m ml acetic acid are stirred under nitrogen at 20 °C. After 5 h the product is filtered off. The product is crystalized from 900 ml ethanol using 2 g charcoal. The ethanol solution is filtered hot. The ethanol solution is cooled to 20 °C and the product is filtered off (yield: 59.5 g (44 percent)).Carbazole (15 g, 92.6 mmol) was added to ethanol (70 mL). Sulfuric acid (6 mL), water (3 mL), -HIOAfter adding 70 mL of ethanol to 15 g of carbazole, 6 mL of sulfuric acid, 3 mL of water, 8.2 g of periodic aciddihydrate, and 9.1 g of iodine were further added at room temperature. The resultant mixture was stirred for 4 h. Theprecipitate generated by adding water to the reaction product liquid was collected by filtration and washed with methanol. The obtained solid was dissolved in hot toluene and recrystallized. The purified solid was vacuum-dried to obtain 5.1 gof white solid, which was identified as Intermediate 1 shown below by FD-MS analysis.To an ethanol solution (500 mL) of carbazole (2.50 g, 15.0 mmol), NaIOTo an ethanol solution (500 mL) of carbazole (2.50 g, 15.0 mmol), NaIO

Pharmaceutical intermediates are also important intermediates for the synthesis of optoelectronic materials

Molecular Weight:293.10
XLogP3:4.4
Hydrogen Bond Donor Count:1
Exact Mass:292.97015
Monoisotopic Mass:292.97015
Topological Polar Surface Area:15.8
Heavy Atom Count:14
Complexity:218
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes