2-Bromo-9-phenyl-9H-carbazole

off-white powder

After mixing compound C-7-2 (23 g, 0.093 mmol), iodobenzene (20.9 mL, 0.186 mol), CuI (14.2 g, 0.074 mol), Cs[165] After mixing compound 1-3 (10 g, 40.63 mmol), CuI (3.8 g, 20.3 mmol), KAfter introducing 2-bromocarbazole 100 g (0.406 mol), iodobenzene 166 g (0.813mol), copper iodide 38.7 g (0.203 mol), ethylenediamine 27 mL (0.406 mol), cesiumcarbonate 265 g (0.813 mol), and toluene 1.3 L in a reaction container, the mixture wasstirred under reflux for 3 hours. After the reaction, the mixture was washed withdistilled water, and an organic layer was extracted with ethyl acetate. The extractedorganic layer was dried with magnesium sulfate, and the solvent was removed using arotary evaporator. The remaining substance was then purified with column chromatographyto obtain compound 2-1 (116 g, 90percent).After mixing compound C-62-2 17 g (69.07 mmol), iodobenzene 15.4 mL (138.15 mmol), CuT 10.5 g (55.26 mmol), ethylenediamine (EDA) 6.9 mL (103.6 mmol), Cs2 CO3 56.26 g (172.6 mmol), and toluene 350 mL, the mixture was stuffed under reflux. After 4 hours, the mixture was cooled to room temperature, and filtered under reduced pressure. The remaining solution was filtered under reduced pressure, and separated with a column to obtain compound C-62-3 20 g (89 percent).A pressure vessel was charged with -bromo-9H-carbazole (10 mmol), iodobenzene (20 mmol), potassium carbonate (20 mmol), L-proline (2 mmol), copper(I) iodide (1 mmol), and dimethyl sulfoxide (25 mL). Compound 1-2 (30g, 101.29mmol), iodobenzene (41.3g, 202.59mmol), CuI (9.6g, 50.64mmol), CsPreparation of compound 1-3 [100] After mixing compound 1-2 (30 g, 101.29 mmol), iodobenzene (41.3 g, 202.59 mmol), CuI (9.6 g, 50.64 mmol) and CsTo a round bottom flask Sub 1-1-1 (4.9g, 20mmol), Sub 1-2-1 (4.1g, 20mmol), Pd2(dba)3 (0.9g, 1mmol), PPh3 (0.5g, 2mmol), NaOt-Bu (5.8g, 60mmol), toluene (210mL) added and allowed to react at 100 °C. When the reaction is complete, the ether and water are added to the resulting solution. The organic layer was dried over MgSO4, concentrated and recrystallized silicagel column and extracted Sub 1-3-1, 5.4g (yield: 84percent) was obtained.[271] In a 100 ml round-bottom three-neck flask under a nitrogen atmosphere, 4.2 g of Intermediate 20, 5.2 g of iodobenzene, 0.3 g of copper iodide, 0.3 g of1, 10-phenanthroline, 7.1 g of potassium carbonate and 50 ml of dimethylfomiamide were placed, and reacted at 80°C for 24 hrs. The reaction solution was cooled and then extracted with dichloromethane and water. The extracted solution was concentrated, subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane and then concentrated, thus obtaining 4.8 g of Intermediate 21 (yield 8 1percent).[272] MS (ESI): [M+H]+ 322The obtained Sub 1-II-B1 (37.19g, 151.1mmol) was dissolved in nitrobenzene in a round bottom flask, and iodobenzene (46.24g, 226.7mmol), NaIntermediate B 1mol and iodobenzene 1.5mol After dissolved in nitrobenzene, Na2SO4, K2CO3, the Cu It was added and the resulting mixture was stirred at 200°C . After the reaction is complete when the nitrobenzene removed by distillation and extracted with water and CH2Cl2 and the organic layer over anhydrous MgSO4 Dried and concentrated to give the desired intermediate C and the resulting product was purified by column chromatography and recrystallization after (yield: 79percent).Under nitrogen atmosphere, intermediate Compound B 2.45g (10mmol), iodobenzene and 3.06g (15mmol) was dissolved in 25ml nitrobenzene, K2CO3 4.15g (30mmol) and Cu 0.19g (3mmol) was added and the mixture was refluxed for 16 hours. After completion of the reaction, MC 100ml, H2O 100ml was added and then the the MC layer was extracted, concentrated and separated by column chromatography using Hex : EA =5 : 1 and dried over anhydrous MgSO4 to give the intermediate C 2.48g (77percent).Sub 1-II-1 (80.34g, 326.5mmol) nitrobenzene (653 ml) for in round bottom flask senses a rotation velocity of the disk in, iodobenzene (99.9g, 489.7mmol), Na It was dissolved Sub 1-II-1 (80.34g, 326.5mmol) obtained in the above synthesis in nitrobenzene (653ml) in a round bottom flask, iodobenzene (99.9g, 489.7mmol), Na2SO4 (46.37g, 326.5mmol), K2CO3 ( 45.12g, 326.5mmol), was added Cu (6.22g, 97.9mmol) and stirred at 200 . After completion of reaction was removed by distillation to nitrobenzene and extracted with CH2Cl2 wamul. The resulting compound and the organic layer was dried over MgSO4 and concentrated to silicagel column and the product was recrystallized 76.78g: (yield: 73percent).Sub 1-II-1 (80.34g , 326.5mmol) was dissolved in nitrobenzene (653ml) in a round bottom flask, iodobenzene (99.9g, 489.7mmol), Na 2 SO 4 (46.37g, 326.5mmol), K 2 CO 3 was added (45.12g, 326.5mmol), Cu ( 6.22g, 97.9mmol) and the resulting mixture was stirred at 200 . After completion ofreaction by distillation to remove nitrobenzene and the CH 2 Cl 2 and extracted with water. The organic layer is MgSO 4 and the resulting compoundwas dried and concentrated to a silicagel column and the product was recrystallized 76.78g: (yield: 73percent).Sub 1-II-1 (113.37g, 460.7mmol) obtained in the above synthesis was dissolved with nitrobenzene in a round bottom flask, iodobenzene (140.97g, 691mmol), Na2SO4 (65.43g, 460.7mmol), K2CO3 (63.67g, 460.7 mmol), was added Cu (8.78g, 138.2mmol) and stirred at 200° C. After completion of reaction was removed by distillation to nitrobenzene and extracted with CH2Cl2 wamul. The resulting compound and the organic layer was dried over MgSO4 and concentrated to silicagel column and recrystallized to give the product 108.35g (73percent yield).Sub-1-II-1 (80.34g, 326.5 mmol) obtained in the above Synthesis was added to a round bottom flask and dissolved in nitrobenzene 653 mL, iodobenzene (99.9 g, 489.7 mmol), Na2SO4 (46.37 g, 326.5 mmol), K2CO3 (45.12 g, 326.5 mmol), and Cu (6.22 g, 97.9 mmol) were added and the resulting mixture was stirred at 200 ° C. After completion of reaction, nitrobenzene was removed by distillation, extracted with water and CH2Cl2, the resulting material was purified by silicagel column, and the organic layer was dried over MgSO4, and concentrated to obtain product 76.78 g (yield: 73percent).In argon stream, a mixture obtained by successively mixingthe intermediate 2 (20 g 81 mmol) iodobenzene (18.1 g 89mmol), copper iodide (1.5 g, 8 mmol), tripotassium phoshtermediatephate (34.5 g, 163 mmol), dry dioxane (100 mE), and cycloxylene hexanediamine (1.8 g, 16 mmol) was stirred at 80° C. for 8 h.After cooling the reaction liquid to room temperature, theorganic layer was separated and the organic solvent wasremoved from the organic layer by distillation under reducedpressure. The obtained residue was purified by a silica gelcolunm chromatography to obtain the intermediate 14 (18.3 g, yield: 70percent). The identification of the intermediate 14 wasmade by FD-MS (field desorption mass spectrometry) analy50 sis.In a 0.5 L reaction flask, 10.0 g (40.6 mmol) of the compound [119-1], 10.7 g (44.7 mmol) of the compound [119-2] 5.9 g (60.9 mmol) of sodium butoxide, and 150 ml of toluene were placed, and the mixture was stirred at room temperature. 0.1 g (0.4 mmol) of palladium acetate, 0.3 g (0.8 mmol) of tri-tert-butylphosphine (50percent) And the mixture was stirred under reflux for 15 hours under a stream of nitrogen. After completion of the reaction, the mixture was slowly cooled to room temperature, and then the reaction solution was poured into a saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by column chromatography to obtain 9.0 g (69percent) of intermediate compound [119-3].A mixture solution of 2-bromo-9H-carbazole (10.0 g, 40.6 mmol), iodobenzene (12.43 g, 61.0 mmol), CuI (0.774 g, 4.06 mmol), (1R, 2S)-cyclohexane-1, 2-diamine (0.987 ml, 8.13 mmol), and KA 500ml reactor 2-bromo mocha carbazole (30g, 121.9mmol), iodobenzene (38.3g, 243.8mmol), copper chloride (I) (0.24g, 2.4mmol), potassium carbonate (20.2g, 146.3mmol), dimethyl Insert the sulfoxide 240 mL was refluxed for 24 hours.After completion of reaction, after cooling to room temperature, into a 200mL ethyl acetate was filtered through a Buchner.Extract the filtrate with water 500 mL, under reduced pressure and then dry the organic layer was treated to remove the organic solvent.Hexane: ethyl acetate (10: 1) the column was isolated using as a developing solvent.19.8g of a white solid to give the 2-bromo-phenyl -N- carbazole.(50.4percent).30.51 g (149.56 mmol) of iodobenzene, 18.32 g (74.78 mmol) of 2-bromo-9H-carbazole, 14.37 g (149.56 mmol) of sodium t-butoxide, and 1.81 ml (7.48 mmol) of tritertbutylphosphine were dissolved in 300 ml of toluene, and 0.68 g (0.75 mmol) of Pd

Molecular Weight:322.2
XLogP3:5.7
Rotatable Bond Count:1
Exact Mass:321.01531
Monoisotopic Mass:321.01531
Topological Polar Surface Area:4.9
Heavy Atom Count:20
Complexity:338
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes