2-BroMo TriphenylaMine

30 g (0.177 mol) of diphenylamine, 49 g (0.355 mol) of potassium carbonate and 3.5 g (0.035 mol) of copper chloride were added to a 500 mL round bottom flask, 300 mL of dimethyl sulfoxide was added to 75.2 g (0.266 mol) of 2-bromoiodobenzene, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted. The organic layer was concentrated under reduced pressure, recrystallized with hexane, and dried to obtain 48.1 g (83.7percent) of the compound represented by the formula (I-a)To a round bottom flask, 1-bromo-2-iodobenzene (5.7g, 20mmol), diphenylamine (3.4g, 20mmol), Pd2 (dba) 3 (0.9g, 1mmol), PPh3 (0.5g, 2mmol), NaOt-Bu ( 5.8g, 60mmol), and the reaction allowed to proceed at 100°C after the into toluene (210mL). After completion of reaction, the organic layer was dried over MgSO4, and extracted with water and ether and recrystallized silicagel column and the resulting organics concentrated and the product was 4.9g: (yield: 76percent).To a round bottom flask, 1-bromo-2-iodobenzene (5.7g, 20mmol), diphenylamine (3.4g, 20mmol), Pd2 (dba) 3 (0.9g, 1mmol), PPh3 (0.5g, 2mmol), NaOt-Bu ( 5.8g, 60mmol), and the reaction proceeds at 100 C after the into toluene (210mL). After the reaction was completed, the organic layer was dried and extracted with water and ether and recrystallized with MgSO4 and concentrated to silicagelcolumn The resulting organic product was 4.9g: (yield: 76percent).in round bottom flask 1-bromo-2-iodobenzene (5.7g, 20mmol), diphenylamine (3.4g, 20mmol), Pd General procedure: General procedure for the palladium-catalyzed reaction The 2.8g (10mmol) 2- bromo-iodobenzene b-1, 2g (12mmol) diphenylamine b-2, sodium tert-butoxide 1.4g (15mmol), palladium acetate 0.1g (0.5mmol) and bis diphenylphosphino 0.28 g (0.5mmol) was added 30mL of toluene, the reaction was stirred for 12h at 100 .The reaction was cooled to room temperature and the end, reaction was quenched with 100mL water.Then purified with dichloromethane (extracted three times with dichloromethane 30mL) the organic phase is extracted, the solvent rotary evaporated off to column chromatography method (a volume ratio of n-hexane mobile phase:: dichloromethane = 19) The product, a pale yellow solid B 2.4g, 74percent yield.3 g of diphenylamine, 7 grams of 2-bromoiodobenzene, 0.1 g of 1, 10-morpholine, 0.12 g of CuI (1) and 7.8 g of KOH were placed in a round bottom three-necked flask under a nitrogen atmosphere, And 20 ml of toluene was added.The mixture was stirred and refluxed.After completion of the reaction, the resulting solution was washed with dichloromethane and water. Collecting organic layer, Dried over MgSO4 and separated by column, Thus, 3.0 g of intermediate 15 was obtained (yield 52percent).2-necked flask, 500mL of diphenylamine (diphenylamine) (12.5g, 73.6mmol), 1- bromo-2-iodo-benzene (1-bromo-2-iodobenzene ) (25g, 88.4mmol), copper iodide (CuI) to (0.701g, 3.68mmol), potassium carbonate (KIn a 250ml flask dissolve diphenylamine (12.5 g, 73.6 mmol), 1-bromo-2-iodobenzene (25 g, 88.4 mmol), CuI (0.701 g, 3.68 mmol) and K2CO3 (20.4 g, 147 mmol) by reflux stirring at 120 ° C. The mixture was cooled to room temperature, extracted with CH2Cl2, dried over MgSO4, and then the solvent was removed. Column chromatography with hexane solvent gave 8.95 g (37.3percent) of white solids.1-bromo-2-iodobenzene (17.9 g, 63.3 mmol), diphenylamine (8.9 g, 52.6 mmol), K2CO3 (14.6 g, 105.6 mmol) and copper iodide (0.5 g, 2.6 mmol) were dissolved in p-xylene (250 ml) and refluxed for 24 hours. After cooling to room temperature, the mixture was concentrated under reduced pressure. Column chromatography using MC: Hx gave Compound 8-4 (5.0 g, 30percent).Diphenylamine (1.6900 g, 10.0 mmol), o-dibromobenzene (2.40 mL, 20.0 mmol), copper iodide (0.1900 g, 1.0 mmol), 18-crown-6 (0.1320 g, 0.5 mmol), and 60 mL of o-dichlorobenzene were sequentially added to the reaction flask. Under nitrogen protection and dark conditions, stir and heat to 100-210°C for 5-100 hours. Stop the reaction and slowly reduce to room temperature, vacuum distillation of most of the solvent, suction filtration, The solid residue is washed with dichloromethane solution and the organic phases are combined. Concentration and column chromatography gave N-2-bromophenyl-N-diphenylamine (yield: 73percent)2-Bromotriphenylamine (4.52 g, 13.98 mmol) was added to a three-neck reaction flask, and THF (100 mL) was added and dissolved, and the mixture was replaced with nitrogen three times. The temperature was lowered to -78 C in a nitrogen atmosphere, and after the temperature was reached, the control temperature was slowly added dropwise to -65 C to n-BuLi (0.357 mL, 13.98 mmol), and the mixture was stirred for 30 min. Further, Compound A (2 g, 6.66 mmol) was dissolved in 30 mL of THF, and then slowly added dropwise to the reaction mixture. After the completion of the dropwise addition, the mixture was naturally allowed to react to room temperature for 6 hours. After the reaction was completed, ice water (100 mL) was added to quench the reaction. Further, DCM (80 mL × 2) was added for extraction, and finally extracted once with saturated brine. The organic phase was collected and rotary evaporated to give a pale yellow oil. 20 mL of acetic acid was added to the oil, and the mixture was heated to reflux for 6 hours. After the reaction was completed, H2O (100 mL) was added to the reaction mixture, and the mixture was filtered and washed with water.Dry to give a white solid M1 (1.1 g, 1.45 mmol)The yield was 22%.To a solution of 2-bromotriphenylamine (1.62 g, 5.00 mmol) inanhydrous tetrahydrofuran (40 mL) was added 5.50 mmol solution of nbutyllithiumin hexane at -78 C under a nitrogen atmosphere. Afterstirring for 1 h, 4-bromobenzophenone (1.44 g, 5.50 mmol) was addedand the mixture was stirred at -78 C for 1 h, with the temperaturegradually rising to room temperature overnight. Then water was addedto the mixture to quench the reaction. The mixture was extracted withdichloromethane and water, and the organic layer was dried over anhydroussodium sulfate, filtered and evaporated. The resulting crudeintermediate was dissolved in 25 mL acetate acid and 2.5 mL hydrochloricacid. The solution was refluxed for 4 h and then cooled to roomtemperature and filtered. The mixture was purified by silica gel columnchromatography using petroleum ether as eluent. The 9-(4-bromophenyl)-9, 10-diphenyl-9, 10-dihydropyridine (BDPDHR) was collectedas a white powder (1.63 g, 67% yield) and dried at 40 C overnight in avacuum oven before use. M.p.: 233.5-234.1 C. 1H NMR (400 MHz, DMSO-d6, ppm): 7.64 (dd, J=8.3, 6.9 Hz, 2H), 7.59-7.49 (m, 3H), 7.31(dq, J=12.8, 7.0 Hz, 3H), 7.08 (dtd, J=8.5, 3.7, 1.5 Hz, 4H), 6.95-6.81 (m, 6H), 6.76 (dd, J=7.8, 1.5 Hz, 2H), 6.33 (dd, J=8.3, 1.2 Hz, 2H); 13C NMR (126 MHz, Chloroform-d) delta 145.98, 145.71, 142.12, 140.50, 132.13, 131.22, 130.73, 130.59, 130.37, 129.83, 128.81, 128.33, 127.77, 127.07, 126.50, 120.25, 114.11, 56.43. FT-IR (KBrpellet) nu: 3060, 3031, 1591, 1487, 1470, 1453, 818, 750 cm-1; MALDITOF-MS m/z: calc. for C31H22BrN [M-H] +: 487.1; found 487.1; Anal.calcd (%) for C31H22BrN: C, 76.23; H, 4.54; N, 2.87. Found: C, 76.65; H, 4.45; N, 7.91

Molecular Weight:324.2
XLogP3:5.9
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:3
Exact Mass:323.03096
Monoisotopic Mass:323.03096
Topological Polar Surface Area:3.2
Heavy Atom Count:20
Complexity:263
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes