2-BROMO-4,6-DIPHENYL-[1,3,5]TRIAZINE

Under a nitrogen atmosphere, add 1-4 (31.78 g, 100.05 mmol) to the 2L reactor.1-2 (12.19 g, 100.01 mmol), potassium carbonate (1.24 g, 9.00 mmol), 200 mL of toluene was stirred.The temperature in the reactor was raised to 70°C and Pd(PPh3)4 (1.04 g, 0.90 mmol) was added.100 mL of distilled water was stirred, and the mixture was stirred and refluxed for 11 h to fully react.After adding 70 mL of distilled water to stop the reaction, the mixture was filtered under reduced pressure, and the solid was washed with distilled water, followed by acetone.Recrystallization from toluene, THF, solidification followed by sublimation, toluene recrystallization, Intermediate 1-5 30.89 g was obtained with a yield of 84.10percent.In a 250 ml round bottom flask, H002-3 (10 mmol), 4-bromo-2, 6-diphenyltriazine (12 mmol) and Pd(PPh3)4 (0.3 mmol) were added to toluene (30 ml) / ethanol ( A mixture of 20 ml) and potassium carbonate (12 mmol) in water (10 ml) was refluxed for 12 h under nitrogen atmosphere. The resulting mixture was cooled to room temperature, added to water, then filtered over a pad of celite, and the filtrate was extracted with methylene chloride, and then washed with water and dried over anhydrous magnesium sulfate, filtered and evaporated. The product gave the final product H002.A rnixture of Compound A (618 mg, 1.83 mmol), 2-bromo-4, 6-diphenyl- 1, 3, 5 -triazine (689 mg, 2.20 mmol), Pd(PPh3)4 (110 mg, 0.0918 mmol), potassium carbonate (774 mg, 5.51 mmol) in degassed deionized water (3 mL) and degassed THF (9 mL) solution was stirred at 80 C under a nitrogen atmosphere for 17 h. After cooled to room temperature, the reaction mixture was filtered through a Celite pad rinsed by chloroform, and the resulting filtrate was evaporated in vacuo. The obtained residue was purified by column chromatography on silica gel using 3:2 (v/v) hexane/toluene as eluent to afford a white solid (0.484 g, 57.0%). TlNMR (500 MHz, CDCk d): 8.75 (d, J= 8.0 Hz, 41 1). 8.45 (d. ./ 8.5 Hz, 2H), 7.67 (t, J = 7.5 Hz, 2H), 7.61 (t , J = 7.5 Hz, 41 1). APCI-MS m/z : 373.1 M2A doubled-necked flask equipped with a stir bar was charged with 2, 3, 4, 6- tetrafluorobenzonitrile (1.52 g, 8.57 mmol), 2-bromo-4, 6-diphenyl- 1, 3, 5-triazine (2.68 g, 8.57 mmol), potassium carbonate (1.79 g, 12.85 mmol), palladium acetate (58 mg, 0.26 mmol) and tricyclohexylphosphine (218 mg, 0.771 mmol), which was evacuated and refilled with nitrogen for three times. The reaction mixture was added 2-ethylhexanoic acid (0.14 mL, 0 857 mmol) and xylene (50 mL) and was stirred at room temperature for 15 min, then heated to 130 C. After stirring for 5 h, the reaction mixture was cooled to room temperature, diluted with CHCb (10 mL) and water (10 mL), and filtered through Ceiite pad followed by washing with CHCb and water. The aqueous layer was separated and extracted with CHCb (20 mL). The combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. The solvents were evaporated under vacuum, and the crude product was purified by silica gel column chromatography using 2: 1 (v/v/v) hexane /CHCb as eluent to afford pale yellow solid (0 45 g, 412.9%). NMR (500 MHz, CDCb, d): 8.67 (d, J = 7 5 Hz, 4H), 7.65 (t, ./ 7 5 Hz, 2H), 7.58 (l. ./ 8.0 Hz, 41 1 ). ESI-MS m/z: 407 M rUnder nitrogen protection, weighed compounds S18 (4.5 mmol), S19 (4.8 mmol), [Pd2 (dba) 3] · CHCI3 (0.25 mmol) and HP (tBu) 3 * BF4 (0.45 mmol), and added to 250 mL. The two-necked flask. Into the two-necked flask, 60 mL of toluene was injected (pre-pass No 15 min to remove oxygen), and then 6 mL of a 1 M K2C03 aqueous solution was added dropwise (Advance No.)It was dehydrated at 15 min and stirred at room temperature overnight. After the reaction was completed, 15 mL of deionized water was added, and a few drops of 2MHC1 were added dropwise. Extracted with dichloromethane, the organic phase was collected and dried over anhydrous Na2SO. The dried solution was filtered, and the solvent was removed on a rotary evaporator to give a crude material. The crude product was purified by column chromatography on silica gel eluting to afford a solid S20 (3.42 mmol, 75%)In a 250 ml round bottom flask, H55-2 (10 mmol), 4-bromo-2, 6-diphenyltriazine (12 mmol)And Pd(PPh3)4 (0.3 mmol) was added to a mixture of toluene (30 ml) / ethanol (20 ml) and potassium carbonate (12 mmol) (10 ml), The reaction was refluxed for 12 h under a nitrogen atmosphere.The resulting mixture was cooled to room temperature, added to water and then filtered through a pad of Celite.The filtrate was extracted with dichloromethane, then the organic phase was washed with water and dried over anhydrous magnesium sulfate.After filtering and evaporating the organic phase, the crude product was purified by silica gel column chromatography.The final product H55 was obtained.General procedure: Compound 3-1 (7.6 g, 20 mmol) and iodobenzene (5.7 g, 20 mmol) were dissolved in toluene (80 mL), then Pd(PPh3)4 (1.1 g, 1 mmol) and K2CO3 (8.3 g, 60 mmol) were added thereto, and the result was stirred for 10 minutes. After that, H2O (16 mL) and EtOH (16 mL) were added thereto, and the result was refluxed for 12 hours. After the reaction was completed, the result was cooled to room temperature, and extracted with distilled water and Mc. After the organic layer was dried with anhydrous Na2O4, the solvent was removed using a rotary evaporator, and the result was purified using column chromatography with ethyl acetate and hexane as a developing solvent to obtain target Compound 3 (8.3 g, 95%).Compound 237-4 (8 g, 0.019 mol), Compound 1 (10 g, 0.023 mol), Compound 926-4 (9.8 g, 0.020 mol), Compound 1-4 (11.4 g, 0.026 mol),

Molecular Weight:312.16
XLogP3:4.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:311.00581
Monoisotopic Mass:311.00581
Topological Polar Surface Area:38.7
Heavy Atom Count:19
Complexity:249
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes