[ CAS No. 1342892-15-2 ] {[proInfo.proName]}

Name: 1342892-15-2|10-(4-Bromophenyl)-9,9-dimethyl-9,10-dihydroacridine|98%
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Product Details of [ 1342892-15-2 ]

CAS No. :	1342892-15-2	MDL No. :	MFCD29919158
Formula :	C₂₁H₁₈BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YKFRPCRADQOKOA-UHFFFAOYSA-N
M.W :	364.28	Pubchem ID :	90184035
Synonyms :

Safety of [ 1342892-15-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1342892-15-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1342892-15-2 ]

[ 1342892-15-2 ] Synthesis Path-Downstream 1~11

1
[ 121-43-7 ]
[ 1342892-15-2 ]
[ 1246021-61-3 ]

Yield	Reaction Conditions	Operation in experiment
70.1%	Stage #1: 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydro-acridine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran Inert atmosphere;	6 3.42 g of intermediate 5 (9.42 mmol) were weighedIn a 100 mL dry two-necked flask,50 mL of dry tetrahydrofuran was added as the reaction solvent.Under nitrogen protection,This was cooled to -78 & lt; 0 & gt; C with liquid nitrogen acetone,The mixture was stirred at this temperature for 5 min,Under a nitrogen atmosphere, 8.85 mL (1.6 mol / L, 14.13 mmol) of n-butyllithium was added dropwise to the reaction system using a syringe.After 1 hour of reaction,To the reaction system, 2.15 ml (8.8 mol / L, 18.84 mmol) of trimethyl borate was added dropwise,And allowed to stir overnight with natural warming.After the reaction, the reaction was quenched by the addition of dilute hydrochloric acid solution.The reaction solution was extracted with dichloromethane (100 mL x 3)The extracts were combined and dried over anhydrous magnesium sulfate,The solvent was removed and dried.The crude product was purified by column chromatography using dichloromethane and ethyl acetate as the eluent gradient,To obtain 2.18 g of a white solid,Yield 70.1%
66%	Stage #1: 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydro-acridine With n-butyllithium In tetrahydrofuran at -78℃; for 0.166667h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -78℃; for 0.333333h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
66%	Stage #1: 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydro-acridine With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Schlenk technique; Stage #2: Trimethyl borate In tetrahydrofuran at 20℃; for 12h; Schlenk technique;

Reference： [1]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN106243086, 2016, A Location in patent: Paragraph 0014
[2]Zhang, Qisheng; Kuwabara, Hirokazu; Potscavage, William J.; Huang, Shuping; Hatae, Yasuhiro; Shibata, Takumi; Adachi, Chihaya [Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18070 - 18081]
[3]Park, Hee-Jun; Han, Si Hyun; Lee, Jun Yeob [Chemistry - An Asian Journal, 2017, vol. 12, # 18, p. 2494 - 2500]

2
[ 6267-02-3 ]
[ 589-87-7 ]
10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydro-acridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With copper(l) iodide; rac-diaminocyclohexane; sodium t-butanolate; In 1,4-dioxane; for 6h;Inert atmosphere; Reflux;	100 mL of 1,4-dioxane was placed in a flask having been substituted with nitrogen, to which 9,9-dimethyl-9,10-dihydroacridan (10 g, 47.8 mmol), 1-bromo-4-iodobenzene (14.9 g, 52.58 mmol), copper iodide (0.18 g, 0.96 mmol), sodium tert-butoxide (9.2 g, 95.6 mmol), and 1,2-diaminocyclohexane (0.55 g, 4.78 mmol) were then added. The reaction solution was heated and refluxed for 6 hours. Thereafter, the temperature was lowered, and impurities were removed with Celite. The resulting filtrate was purified by column chromatography to provide an intermediate (1) as a white solid matter (15.5 g, 89%). 1H NMR (500 MHz, CDCl3): 7.75 (d, J=8.5 Hz, 2H), 7.45 (dd, J=9.5 Hz, 2 Hz, 2H), 7.22 (d, J=8.5 Hz, 2H), 6.95 (m, 4H), 6.24 (dd, J=9.5 Hz, 1.5 Hz, 2H), 1.54 (s, 6H)
80%		<strong>[6267-02-3]9,9-dimethyl-9,10-dihydroacridine</strong> (760 mg, 3.6 mmol) was added to a 50 mL two-neck eggplant flask and purged with nitrogen. Thereafter, dry toluene (11 mL) was added to the reaction vessel and cooled to 0 C. with ice. To this solution was added 1.55 M n-BuLi n-hexane solution (2.5 mL, 1.1 eqiv, 3.9 mmol) dropwise and stirred at 0 C. for 1 h.Thereafter, Pd2 (dba)3 .CHCl3 (190 mg, 5.0 mol%, 1.8 × 10 mmol), 2- (di-tert-butylphosphino) biphenyl [John Phos] (140 mg, 12 5 mol, 4.5 x 10 mmol), 1-bromo-4-iodobenzene (3.6 g, 3.5 equiv, 13 mmol) and dry toluene (3 mL) and the mixture was stirred at 50 C. for 18 hours. After the reaction, filtration with Celite, methylene chloride was added to the reaction solution, and the organic layer was extracted by washing with purified water and saline. Then it was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel chromatography to obtain the objective compound 1 (1.1 g, yield 80%) as a white solid.
75%		9,9-Dimethyl-9,10-dihydroacridine (2.09 g, 10 mmol), p-bromoiodobenzene (3.1 g, 11 mmol), iodideCopper (0.38 g, 0.2 mmol) and sodium tert-butoxide (1.92 g, 20 mmol) were added to the reaction flask, and nitrogen was exchanged three times (10 min/time).The solvent (1,4-dioxane) was injected under the protection of nitrogen, and 2 ml of 1,2-diaminocyclohexane was injected after the raw material was partially dissolved.(Reagent), after the injection is completed, the reaction is refluxed at 110 C for 6 h, extracted, concentrated, powdered, separated and purified by column chromatography to obtain white.Color solid product 2, yield 75%.

74.7%	With copper(l) iodide; In 1-methyl-pyrrolidin-2-one; at 120℃; for 12h;	5g (23 · 9mmol) of 9,9-dimethylacridine and 7.4g (26.3mmol) of 4-bromoiodobenzene were mixed.457 mg (2.4 mmol) of cuprous iodide was added,Then add 50ml of NMP,Stir and heat at 120C for 12 hours.After cooling to room temperature, the mixture was filtered, and the filtrate was poured into 500 ml of water and filtered. The filter cake was washed with water to give a white solid, which was recrystallized from ethanol to give 6.5 g of a white solid. The yield was 74.7%.
74%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; for 3h;Inert atmosphere; Reflux;	S7 (2.5 mmol), S8 (2.6 mmol), (dibenzylideneacetone) dipalladium (0) (0.12 mmol),Sodium tert-butoxide (4 mmol) and tri-tert-butylphosphine tetrafluoroborate (0.25 mmol) were put into a 100 mL three-necked flask,While stirring, degassing and nitrogen replacement were repeated 3 times quickly, and 40 mL of toluene was added via a syringe.The mixture was heated under reflux under a stream of nitrogen for 3 hours.After the reaction, water was added to the reaction solution cooled to room temperature, extraction was performed with dichloromethane, and the solution was washed with saturated brine.After the organic layer was dried with anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography.Intermediate S9 (1.85 mmol, 74%) was obtained.
70%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 70 - 105℃; for 12h;Inert atmosphere; Reflux;	Under the protection of nitrogen, add 9,9-dimethylacridine 50mmol, p-bromoiodobenzene 50mmol, toluene 105mL and 100mmol sodium tert-butoxide to the reaction flask, stir and heat to 70-80 , then quickly add three 5 mmol of tert-butylphosphine in toluene solution and 10 mmol of Pd2 (dba) 3. After the addition, the temperature was continuously raised to 100-105 C and the reaction was refluxed for 12 hours. After the reaction was completed, the temperature was lowered, and the organic phase was extracted with water, washed, dried, and filtered. concentrate. After passing through the column with a mixed solvent of dichloromethane and n-heptane, it was recrystallized to LC> 99.5%, and dried to obtain compound 10- (4-bromophenyl) -<strong>[6267-02-3]9,9-dimethyl-9,10-dihydroacridine</strong>. , Ie intermediate 1 (yield 70%).
65.8%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; at 80℃; for 20h;Inert atmosphere;	4.0 g (11.12 mmol) of <strong>[6267-02-3]9,9-dimethyl-9,10-dihydroacridine</strong> was weighed2.44 ml (5.40 g, 11.12 mmol) of bromoiodobenzene,3.98 g (38.24 mmol) of anhydrous sodium tert-butoxide,1.46 ml (0.58 mmol) of tri-tert-butylphosphine,0.086 g (0.38 mmol) of palladium acetate in a 250 mL three-necked flask,Then, 100 mL of anhydrous toluene was added as a reaction solvent.Under nitrogen protection,And the mixture was heated to 80C for 20 hours.After completion of the reaction,After the solvent was removed under reduced pressure, dichloromethane (100 mL × 3) was added to extract the reaction solution,The extracts were combined and dried over anhydrous magnesium sulfate,Spin dry solvent.The crude product was purified by column chromatography using petroleum ether and methylene chloride (PE: DCM = 15: 1)4.56 g of a white crystalline powder was obtained,The yield was 65.8%.
65.7%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In tetrahydrofuran; at 80℃; for 20h;Inert atmosphere;	Weigh 2.0 g (9.56 mmol) of <strong>[6267-02-3]9,9-dimethyl-9,10-dihydroacridine</strong>, 2.70 g (9.56 mmol) of bromoiodobenzene, 18.4 g (191.2 mmol) of anhydrous sodium tert-butoxide, 0.73 ml (0.29 mmol) of tri-tert-butylphosphine, 0.043 g (0.19 mmol) of palladium acetate in a 250 mL three-necked flask, Then 100 mL of dry tetrahydrofuran was added as the reaction solvent. Under nitrogen, heated to 80 C for 20 hours. After the reaction, The reaction solution was extracted with dichloromethane (50 mL x 3) after solvent extraction, The extracts were combined and dried over anhydrous magnesium sulfate, dried to dry the solvent and dried. The crude product was treated with petroleum ether and dichloromethane (PE:DCM=15:1) And the residue was purified by column chromatography to obtain 2.28 g of white crystalline powder, Yield 65.7%.
63%	With tri-tert-butylphosphonium tetrafluoroborate; palladium diacetate; caesium carbonate; In toluene; at 130℃; for 12h;Inert atmosphere;	A three-necked flask was charged with 9,9-dimethylacridine (1 g, 4.78 mmol), p-bromoiodobenzene (1.48 g, 5.26 mmol), palladium acetate (0.14 g, 0.15 mmol), and cesium carbonate (3.89 g, 11.93 mmol), tri-tert-butylphosphine tetrafluoroborate (0.044 g,0.15 mmol), added to 30 mL of dry toluene, and heated to 130 C for 12 h under the protection of nitrogen. After the reaction, the reaction solution was poured into saturated brine, and then subjected to liquid separation extraction with dichloromethane and ethyl acetate, and the solvent was distilled off under reduced pressure. The crude product was subjected to column chromatography to obtain intermediate M3 with a yield of 63%. .
60%	With copper(l) iodide; potassium carbonate; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux;	Under nitrogen protection(14 gg, 0.05 mol) and 9,9 '-dimethylacridine (l (K45g, 0.05piomicron1) were dissolved in 100 mL of DMF under nitrogen atmosphere, And then put the catalyst copper (3.2 g, 27 mmol) and acid addition of potassium carbonate (13.8 g, 0.1 mol),. The system was heated to reflux for 24 hours. After cooling to room temperature, 500 mL of water was added to quench the reaction. The product was filtered to give crude product. The crude product was purified by silica gel column chromatography and the eluent was purified by purification with V ethyl acetate: V n-hexane = 1: 6 to give an off-white powder in a yield of 60%.
53%	With 1,10-Phenanthroline; copper(l) chloride; potassium hydroxide; In toluene; at 120℃; for 24h;Inert atmosphere;	9,9-Dimethyl acridine (5.0 g, 24.7 mmol), 2-bromo-5-iodobenzene (9.06 g, 32·1 mmol), cuprous chloride (489) were sequentially added to a 250 mL single-mouth bottle. Mg, 4.94 mmol), potassium hydroxide (6·92 g, 124 mmol), 1,10-phenanthroline (891 mg, 4.94 mmol) and 130 mL of toluene, and the mixture was stirred at 120 C for 24 h under nitrogen. The reaction solution was cooled to room temperature, extracted with dichloromethane (3×30 mL). The organic layer was washed with brine (3×30 mL), dried, filtered, and evaporated to remove solvent. A white solid was obtained in 4.78 g, yield 53%.
50%		In a 50 mL three-necked flask, 2.09 g (10.00 mmol) of 9,9-dimethylacridine, 3.11 g (11.00 mmol) of 1-bromo-4-iodobenzene, 1.92 g (20.00 mmol) of NaOtBu, 4-Dioxane (20 mL) was added and the mixture was nitrogen-flowed for 1 hour. Thereafter, 40 mg (0.20 mmol) of CuI and 110 mg (1.00 mmol) of L-proline were added and heated to reflux. After 18 hours, the formation of the target product was confirmed by TLC and MS measurement, and the reaction was stopped. Thereafter, the reaction solution was added to 200 mL of water, extracted three times with 100 mL of toluene, dehydrated with sodium sulfate, concentrated, and purified by silica gel column chromatography to obtain 1.82 g (yield 50%) of a white solid.
21%	With potassium carbonate; rac-diaminocyclohexane; copper(l) chloride; In dimethyl sulfoxide; at 110℃; for 16h;Inert atmosphere;	9,10-Dihydro-9,9-dimethylacridine (25.0 g, 119.6 mmol), 1-bromo-4-iodobenzene (38.0 g, 134.3 mmol), cuprous chloride (I) (2.37 g, 23.9 mmol), dimethyl sulfoxide (250 ml), potassium carbonate (33.1 g, 239.2 mmol) and 1,2-diaminocyclohexane (6.8 g, 59.8 mmol). A 500 ml double neck round bottom reaction flask was added, and the reaction system was filled with nitrogen. The system was heated to 110 C in an oil bath. After 16 hours of reaction, the system was cooled and the reaction was poured into 300 ml of water and stirred, followed by acetic acid. After extracting the ethyl ester, the extract is quenched with saturated brine, and then the water is removed with magnesium sulfate and filtered. The filtrate is removed by a rotary evaporator, and then purified by silica gel column chromatography with hexane as eluent. The light brown solid was compound 2-6-b (9.15 g, 21%).
	With copper(l) iodide; sodium butanolate; In 1,4-dioxane; at 80℃; for 6h;	Compound 125 can be synthesized by a person of ordinary skill following Scheme 5 illustrated in FIG. 6. In the first step, compound S5-1 (available for purchase from Acros Organics, CAS No. 589-87-7) is combined with compound S5-2 (available for purchase from ArkPharm, Inc., CAS No. 6267-02-3), nBuONa and Cul in dioxane at 80 C for 6 hours to form compound S5-3. In the second step, compound S5-3 is is added to hexanes and cooled to 0 C before dropwise addition of nBuLi, followed by addition of B(OMe)3. The reaction can be allowed to stir before being quenched with aqueous HC1 to form compound S5-4. In the third step, compound S5-4 can be combined with compound S5-5 (available for purchase from Acros Organics, CAS No 626-39-1), Pd(OAc)2 and K3P04 in THF at 45 C for 24 hours to form compound S5-6. In the fourth step, compound S5-6 can be combined with compound 55- 7 (available for purchase from Acros Organics, CAS No 1692-15-5), Pd(OAc)2 and K3P04 in THF at 45 C for 24 hours to form compound 125. It is understood that steps 1, 2, 3, and 4 can be performed and optimized by a person having ordinary skill in the art without undue experimentation.
	With copper; potassium carbonate; In N,N-dimethyl-formamide; at 160℃; for 24h;Inert atmosphere;	Under a nitrogen atmosphere, <strong>[6267-02-3]9,9-dimethyl-9,10-dihydroacridine</strong> (1 g, 4.78 mmol),4-bromo-1-iodobenzene (1.75g, 6.21mmol),K2CO3 (1.32g, 9.56mmol) and Cu (1.21g, 19.1mmol) were dissolved in 12mLN, N-dimethylformamide (DMF) solution,Stir at 160 C for 24 hours. After returning to room temperature, the reaction mixture was poured into water,It was extracted with dichloromethane, and the organic layer was completely washed with brine, and then dried over anhydrous magnesium sulfate.Purification by silica gel column chromatography gave a white solid.

Reference： [1]Patent: US2019/345095,2019,A1 .Location in patent: Paragraph 0215-0217
[2]Patent: JP2017/137258,2017,A .Location in patent: Paragraph 0083-0089; 0094-0097
[3]Patent: CN109593079,2019,A .Location in patent: Paragraph 0063; 0067; 0068; 0069
[4]Patent: CN107793398,2018,A .Location in patent: Paragraph 0091-0093
[5]Patent: CN110642842,2020,A .Location in patent: Paragraph 0089-0090
[6]Patent: CN111333615,2020,A .Location in patent: Paragraph 0584-0588
[7]Patent: CN110563647,2019,A .Location in patent: Paragraph 0069-0071
[8]Patent: CN106243086,2016,A .Location in patent: Paragraph 0014
[9]Patent: CN106243091,2016,A .Location in patent: Paragraph 0024
[10]Patent: CN109970710,2019,A .Location in patent: Paragraph 0070; 0081; 0082
[11]Patent: CN106699659,2017,A .Location in patent: Paragraph 0047-0050
[12]Patent: CN110183361,2019,A .Location in patent: Paragraph 0020
[13]Chemistry - An Asian Journal,2017,vol. 12,p. 2494 - 2500
[14]Patent: JP2019/137652,2019,A .Location in patent: Paragraph 0063; 0064
[15]Journal of the American Chemical Society,2014,vol. 136,p. 18070 - 18081
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[19]Patent: CN106661001,2017,A .Location in patent: Paragraph 0347; 0348; 0382; 0383
[20]Patent: CN110790742,2020,A .Location in patent: Paragraph 0073-0076

3
[ 1342892-15-2 ]
[ 73183-34-3 ]
[ 1643935-09-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,1'-bis(diphenylphosphanyl)ferrocene; anhydrous potassium acetate In 1,4-dioxane; toluene at 120℃; for 17h; Inert atmosphere;	2-2 [Reaction formula 2-2] In N2in the gas purification system, "f" the compound, double ( pinacone ) diboron (1.2 equivalent), [ 1,1-bis (mortars; concrete ; artificial stone) ferrocene] palladium (II), dichloride stably dichloromethane, 1,1-bis (mortars; concrete ; artificial stone) ferrocene and potassium acetate is added to the light in the flask 1,4-dioxane/toluene (1:1) and stirring in the solvent. After the air bubbles, in the 120 °C mixing solution under the temperature of 17 hours. After the completion of reaction, the solution is cooled to the room temperature, and removing the solvent. Blending with toluene washing and refining, so as to obtain compound "g". (Yield: 90%)
90%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In toluene for 12h; Inert atmosphere; Reflux;	2 Preparation of intermediate M1 Under nitrogen protection, The above-prepared compound (6.76 g, 0.02 mol) And bis-boronic acid pinacid (6 · 10g, 0.024mol) Dissolved in 100 mL of toluene, The catalyst Pd (dppf) C12 (0 · 15g, 0.2 mmol) was then charged, And potassium acetate (5.88 g, 0.06 mol). System temperature to reflux for 12 hours, naturally cooled to room temperature, the filter, remove the salt, the steam to get crude. The crude product was purified by silica gel column chromatography, eluting with V dichloromethane: V n-hexane = 1: 5 to obtain white solid Body, the yield of 90%.
89%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In N,N-dimethyl-formamide at 80℃; for 12h;	2.3 Step 3: Preparation of Intermediate T-5 Will 6g (16.4mmol) of intermediate T-4 and 5g(19.7 mmol) of diboronate pinacol ester mix,Add 2.4g(24.7 mmol) of potassium acetate, 117 mg (0.16 mmol) of PdCl2 (dppf) catalyst and 50 ml of N,N-dimethylformaldehydeCarboxamide, stirred and heated at 80°C for 12 hours, cooled to room temperature, poured into 500ml of water, filtered, and the cake was washed with water.The white solid was isolated and purified by silica gel column to give 6.0 g of a white solid with a yield of 89%.

86%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In toluene at 80℃; for 24h; Inert atmosphere;	1 Add 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydroacridine (5g, 13.7mmol) and bis(pinacolato)diboron (4.2g, 16.5mmol), potassium acetate (8.1g, 82.2mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (603mg, 0.8mmol), 100mL toluene, the mixture is protected by nitrogen Heat to 80°C for 24 hours. Cool to room temperature, spin dry the solvent, extract with dichloromethane (3×30mL), wash three times with water, dry with anhydrous magnesium sulfate, filter, collect the filtrate, spin-dry the solvent, and use petroleum ether: dichloromethane (5:1, v/ v) is the eluent and separated by column chromatography to obtain 4.9 g of the target compound, which is a white solid, with a yield of 86%.
86%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In toluene at 80℃; for 24h; Inert atmosphere;	1 Synthesis of Compound SM3 In a 200mL single-neck bottle, SM2 (5g, 13.7mmol), SM2 (5g, 13.7mmol),Pinacol diboronate (4.2 g, 16.5 mmol), potassium acetate (8.1 g, 82.2 mmol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (603 mg, 0.8 mmol), 100 mL of toluene, and the mixture was heated to 80 °C under nitrogen protection for 24 hours. Cool to room temperature, spin dry the solvent, extract with dichloromethane (3 × 30 mL), wash with water three times, dry over anhydrous magnesium sulfate, filter, collect the filtrate, spin dry the solvent, use petroleum ether: dichloromethane (5:1, v/ v) As the eluent, 4.9 g of the target compound was obtained by column chromatography as a white solid with a yield of 86%.
85%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 110℃; for 8.5h; Inert atmosphere;	2.3 Step 3, synthesis of intermediate product 3: Intermediate 2 (2.5 g, 6.9 mmol), pinacol borate (2.63 g, 10.35 mmol), 1,1'-bis(diphenylphosphino)ferrocene palladium (II) (0.26) g, 0.35 mmol) and potassium acetate (1.35 g, 13.8 mmol) were added to the reaction flask, and nitrogen was exchanged three times (10 min/time), and the solvent (1,4 dioxane) was injected under nitrogen protection.After the completion of the injection, the reaction was refluxed at 110 ° C for 8 h, extracted, concentrated, and powdered, and purified by column chromatography to obtain a white solid product 3 in a yield of 85%.
85%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In tetrahydrofuran at 80℃; for 5h; Inert atmosphere;	1 In a 100ml three-necked flask, first mix X006 (2mmol), pinacol diborate (2.2mmol), (1,1'-bis(diphenylphosphine)ferrocene)dichloropalladium (II) (0.1mmol) ) And potassium acetate (12 mmol) were added separately, and while stirring, degassing and nitrogen replacement were quickly repeated 3 times, and 10 mL of tetrahydrofuran was added via a syringe.Stir at a certain speed, and heat the resulting mixed solution reactant at a reaction temperature of 80°C for 5h; after the reaction is over, cool to room temperature and add 10ml of water, extract with ether, and dry the resulting organic phase with anhydrous sodium sulfate , The solvent was distilled off, and column chromatography was used for purification to obtain intermediate X007 (1.7 mmol, 85%).
85%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 110℃; for 8h; Inert atmosphere;	1.2 Step two: Combine Y-Br (1equiv.), pinacol diborate (1.5equiv.), 1,1-bis (diphenylphosphine)ferrocenepalladium dichloride (II) (0.02equiv.) and potassium acetate (1.5equiv.) were dissolved in 50mL 1,4-dioxane. The reaction mixture was heated to 110°C and stirred for 8 hours under the protection of nitrogen. After cooling to room temperature, 100 mL of water was added to the reaction mixture and extracted with dichloromethane to obtain an organic layer. Finally, the organic layer was concentrated to obtain a crude product, which was separated and purified by silica gel column chromatography to obtain a white solid product Y-Bpin with a yield of 85%.
84%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 80℃; for 12h; Inert atmosphere;	2.2 (2) Synthesis of compound 5 In a nitrogen atmosphere, the reactant 4 (10mmol), bis(pinacolato)diboron(12mmol),Potassium acetate (10mmol), [1,1’-bis(diphenylphosphino)ferrocene]palladium dichloride (Pd(dppf)Cl2,0.5mmol) was added to the reaction and dissolved with 100mL 1,4-dioxane, heated to 80°C and reacted for 12 hours.After the reaction is complete, the reaction is spin-dried, washed with water, and then extracted with dichloromethane,The crude product is purified by column chromatography with petroleum ether/dichloromethane mixed solvent as eluent,A white solid product was obtained with a yield of 84%.
80.6%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In toluene at 120℃; for 24h; Inert atmosphere;	1 Synthesis of compound SM2 Add compound SM1 (2.55g, 7mmol),Pinacol diborate (2.13g, 8.4mmol),1,1'-Bisdiphenylphosphinoferrocene palladium dichloride (0.31g, 0.42mmol),Potassium acetate (3.43g, 35mmol) and toluene (70mL),Under the protection of nitrogen, it was heated and stirred to 120°C, and reacted under reflux for 24h.The Tol solution was spun off under reduced pressure, extracted and washed with DCM (40 mL each time) with water three times,Revolve the organic solvent under reduced pressure, dry over anhydrous magnesium sulfate overnight,Use volume ratio VPE:VDCM=4:1 as eluent for chromatographic separation,2.32 g of white powder was obtained, with a yield of 80.6%.
78%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In tetrahydrofuran at 80℃; for 5h; Inert atmosphere;	In a 100 ml three-necked flask, first S9 (1.8 mmol), bis(pinacolato)diboron(2.2 mmol),(1,1'-bis (diphenylphosphine) ferrocene) dichloropalladium (II) (0.05mmol) and potassium acetate (12mmol) were added separately,While stirring, degassing and nitrogen substitution were repeated 3 times quickly, and 8 mL of tetrahydrofuran was added through a syringe.Stir at a certain speed, and heat the resulting mixed solution reactant under reflux at a reaction temperature of 80 ° C. for 5 h;After the reaction is completed, cool to room temperature and add 6 ml of water, extract with ether, and dry the obtained organic phase with anhydrous sodium sulfate.The solvent was distilled off and purified using column chromatography to obtain Intermediate S10 (1.4 mmol, 78%).
61%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In dimethyl sulfoxide Inert atmosphere; Reflux;	1.4 Step 4: Synthesis of Intermediate 1f In a 250 ml reactor with a thermometer, stirring, and nitrogen protection, intermediate 1e (7 g, 19.3 mmol), pinacol biboronate (6 g, 23.6 mmol), potassium acetate (5 g, 51 mmol), Pd ( dppf) Cl2 (1 g, 1.4 mmol) and DMSO 100 ml, heat the reaction to reflux overnight. The dot plate reaction was completed, suction filtration, and the filtrate was spin-dried for column chromatography to obtain 6.5 g of the product with a yield of 61%.
54%	With anhydrous potassium acetate; triphenylphosphine In toluene at 110℃; for 12h; Inert atmosphere;	3 Add intermediate M3 (5g, 15.5mmol), pinacol diborate (4.73g, 18.6mmol), triphenylphosphine palladium dichloride (0.545g, 0.8mmol), and triphenylphosphine into three-necked flasks (0.41g, 1.6mmol), potassium acetate (6.08g, 62mmol), dissolved in toluene, and reacted at 110 ° C for 12h under the protection of nitrogen. After the reaction, the reaction solution was poured into a saturated sodium chloride solution, and the sample was spin-dried. The intermediate M4 was obtained through column chromatography with a yield of 54%.
53%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 85℃; for 36h; Inert atmosphere;
	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 80℃;
	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate In 1,4-dioxane at 160℃; for 16h; Inert atmosphere;	4.2 Under a nitrogen atmosphere, compound M19 (0.55 g, 1.5 mmol),Pinacol diborate (0.5g, 1.95mmol),Potassium acetate (0.3g, 3mmol) and[1,1'-bis (diphenylphosphino) ferrocene] palladium dichloride (Pd (dppf) Cl2, 0.016 g, 0.02 mmol) was dissolved in 1,4-dioxane (20 mL),After stirring at 160 ° C for 16 hours, it was extracted with ethyl acetate.The organic layer was completely washed with brine, and then dried over anhydrous magnesium sulfate.Purification by silica gel column chromatography gave a white solid.

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - CN105585577, 2016, A Location in patent: Paragraph 0126; 0127; 0128; 0129
[2]Current Patent Assignee: VALIANT CO., LTD. - CN106699659, 2017, A Location in patent: Paragraph 0048-0052
[3]Current Patent Assignee: CHENGZHI SHAREHOLDING CO., LTD. - CN107793398, 2018, A Location in patent: Paragraph 0094-0096
[4]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN111620817, 2020, A Location in patent: Paragraph 0031-0033; 0044
[5]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN113831285, 2021, A Location in patent: Paragraph 0030-0032; 0038-0039
[6]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN109593079, 2019, A Location in patent: Paragraph 0063; 0070; 0071; 0072
[7]Current Patent Assignee: TIANMA MICROELECTRONICS CO., LTD. - CN111848642, 2020, A Location in patent: Paragraph 0079; 0088-0090
[8]Current Patent Assignee: XI AN JIAOTONG UNIVERSITY - CN113429402, 2021, A Location in patent: Paragraph 0019-0021; 0023
[9]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN111675693, 2020, A Location in patent: Paragraph 0037-0040; 0043-0044
[10]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN113429388, 2021, A Location in patent: Paragraph 0032-0034; 0038-0039
[11]Current Patent Assignee: TIANMA MICROELECTRONICS CO., LTD. - CN110642842, 2020, A Location in patent: Paragraph 0092-0094
[12]Current Patent Assignee: SUZHOU AOWEI PHOTOELECTRIC NEW MAT - CN113896723, 2022, A Location in patent: Paragraph 0031-0033; 0040-0041
[13]Current Patent Assignee: DALIAN UNIVERSITY OF TECHNOLOGY - CN109970710, 2019, A Location in patent: Paragraph 0070; 0081; 0083
[14]Gao, Ying; Liu, Haichao; Yang, Bing; Yao, Mingming; Zhang, Shi-Tong; Zhou, Changjiang [Journal of Materials Chemistry C, 2021, vol. 10, # 12, p. 4579 - 4583]
[15]Xie, Gaozhan; Li, Xianglong; Chen, Dongjun; Wang, Zhiheng; Cai, Xinyi; Chen, Dongcheng; Li, Yunchuan; Liu, Kunkun; Cao, Yong; Su, Shi-Jian [Advanced Materials, 2016, vol. 28, # 1, p. 181 - 187]
[16]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN110790742, 2020, A Location in patent: Paragraph 0073; 0077; 0078

4
[ 61676-62-8 ]
[ 1342892-15-2 ]
[ 1643935-09-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydro-acridine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	1 Synthesis of compound M2: Compound 2 (5.00 g, 13.7 mmol) and 150 mL of anhydrous tetrahydrofuran were added to a 250 mL two-necked flask and stirred at -78 ° C for 30 minutes under nitrogen atmosphere, followed by n-butyllithium (2.5 M, 7.14 mL, 17.8). Methyl) was added dropwise to the reaction mixture. After reacting for 1 hour, isopropanol pinacol borate (3.83 g, 20.6 mmol) was added dropwise to the reaction mixture, and after reacting for 2 hours, it was transferred to room temperature overnight. The reaction was stopped and the reaction was quenched by the addition of 20 mL of water. The reaction mixture was extracted with methylene chloride (3×30 mL). The organic layer was washed with water (250 mL), dried, filtered, and evaporated in vacuo to remove solvent. The crude product was washed with petroleum ether: dichloromethane (H = 10:1) Separation column chromatography gave 5.72 g of a white solid, yield 78%.
73%	Stage #1: 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydro-acridine With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; for 2.33h; Inert atmosphere;	4 The intermediate (1) (10 g, 27.4 mmol) and 100 mL of tetrahydrofuran were placed in a flask having been substituted with nitrogen, and stirred at -78° C. 200 mL of tetrahydrofuran having n-butyl lithium (1.6 M, 19.9 mL, 31.8 mmol) having been added thereto was added dropwise thereto over 30 minutes. After completing the dropwise addition, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (5.62 g, 30.14 mmol) was added dropwise thereto over 20 minutes, and the reaction solution was stirred at room temperature for 2 hours. Thereafter, 100 mL of water was added to the reaction solution, and after 30 minutes, chloroform was added, followed by extracting. The resulting organic layer was dried over magnesium sulfate, and a filtrate was obtained by suction filtration. Thereafter, recrystallization was performed from methanol to provide an intermediate (2) as a white solid matter (8.1 g, 73%). 1H NMR (500 MHz, CDCl3): 8.06 (d, J=8.0 Hz, 2H), 7.44 (dd, J=9.0 Hz, 1.5 Hz, 2H), 7.34 (d, J=8.0 Hz, 2H), 6.96-6.89 (m, 4H), 6.24 (dd, J=9.5 Hz, 1.5 Hz, 2H), 1.69 (s, 6H), 1.40 (s, 12H)
	With n-butyllithium In tetrahydrofuran Inert atmosphere;

Reference： [1]Current Patent Assignee: CHANGZHOU UNIVERSITY - CN110183361, 2019, A Location in patent: Paragraph 0020
[2]Current Patent Assignee: KYULUX, INC. - US2019/345095, 2019, A1 Location in patent: Paragraph 0215; 0218-0219
[3]Park, In Seob; Lee, Sae Youn; Adachi, Chihaya; Yasuda, Takuma [Advanced Functional Materials, 2016, vol. 26, # 11, p. 1813 - 1821]

5
[ 1342892-15-2 ]
[ 74246-13-2 ]
[ 1443047-77-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With copper; potassium carbonate; sodium sulfate In nitrobenzene at 190℃; for 12h; Inert atmosphere;	169 Synthesis of Inv-169 Under a nitrogen stream, IC-36 (4.47g, 20.00mmol), 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydroacridine(10.93g, 30.00mmol), copper powder (0.38g, 1.00mmol), K2CO3(5.52g, 40.00mmol), Na2SO4 (5.68g, 40.00mmol) And were mixed nitrobenzene (100 ml), and stirred for 12 hours at 190 ° C. The completion of the reactionAfter, removal of the nitrobenzene, after separating the organic layer with methylene chloride, over MgSO4Water was removed. After removal of the solvent of the organic layer and purified by column chromatography,It was obtained Inv-169 as the target compound (6.38g, 63% yield).
63%	With copper; potassium carbonate; sodium sulfate In nitrobenzene at 190℃; for 12h; Inert atmosphere;	169 [Synthesis Example 169] Synthesis of Inv-169 Under a nitrogen stream, the compound IC-36 (4.47 g, 20.00 mmol),10- (4-bromophenyl) -9,9-dimethyl-9,10-dihydroacridine (10.93 g, 30.00 mmol) Cu powder (0.38 g, 1.00 mmol), K2CO3 (5.52 g, 40.00 mmol),Na2SO4 (5.68 g, 40.00 mmol) andAnd mixing a nitrobenzene (100 ml)And the mixture was stirred at 190 DEG C for 12 hours.After the reaction was completed, the nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4.After removal of the organic layer solvent, the residue was purified by column chromatography to obtain the title compoundInv-169 (6.38 g, yield 63%).

Reference： [1]Current Patent Assignee: SOLUS ADVANCED MATERIALS CO LTD - JP2016/40292, 2016, A Location in patent: Paragraph 0676; 0677
[2]Current Patent Assignee: DOOSAN CORP. - KR101879905, 2018, B1 Location in patent: Paragraph 1513-1515

6
[ 6267-02-3 ]
[ 106-37-6 ]
[ 1342892-15-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With tri-tert-butyl phosphine; palladium diacetate; sodium tertiary butoxide In toluene for 12h; Inert atmosphere; Reflux;	2-1 [Reaction formula 2-1] In N2in the gas purification system, the use of a compound "d" (23.9mmol), 1,4-bis-bromobenzene (35.8mmol), palladium (II) acetate (2mol %), butyl three uncles phosphate (5mol %) sodium and tertiary butyl alcohol (2.03 equivalent) is added to the toluene solvent and stirring. Refluxing the mixed solution and stirred 12 hours. After the reaction is finished, the extraction solution in distilled water and ethyl acetate. From the extraction of using magnesium sulphate remove the moisture in the organic layer, and removing the solvent. The material through the use of hexane and ethyl acetate to carry out wet refining column chromatography, thereby obtaining compound crocatus of the liquid is "f". (Yield: 81%)
79%	With tri-tert-butyl phosphine; potassium-t-butoxide; palladium diacetate In toluene at 130℃; for 0.5h; Inert atmosphere;	1.1 (1) Synthesis of compound U1 Under a nitrogen atmosphere, 1,4-dibromobenzene (10 mmol), 9,9-dimethylacridine (10 mmol), palladium(II) acetate(0.5 mmol),Tri-tert-butylphosphine (0.4 mmol) and potassium tert-butoxide (15 mmol) were dissolved in 12 ml of toluene and heated to 130° C to react for 30 minutes. After the reaction was completed, it was cooled to room temperature, the product was extracted with dichloromethane, washed three times with saturated aqueous sodium chloride solution, and after removing the organic solvent,The crude product petroleum ether:dichloromethane=7:3 (v/v) was used as the eluent and purified by column chromatography to obtain a solid product with a yield of 79%. The results of 1H NMR, 13CNMR, MS and elemental analysis indicated that the obtained compound was the target product.
73%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium tertiary butoxide In toluene at 120℃; for 10h; Inert atmosphere;	2.1 (1) Synthesis of compound 4 Under the protection of nitrogen, add 9,10-dihydro-9,9-dimethylacridine (10mmol), 1,4-dibromobenzene (10mmol),Sodium tert-butoxide (25mmol), catalyst Tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 0.5mmol)The ligand tri-tert-butyl phosphine (1 mmol) was added to 50 ml of toluene, stirred and heated to 120° C., and reacted for 10 hours.After the reaction, the product was extracted with ethyl acetate, washed with saturated sodium chloride solution three times,Dry with anhydrous sodium sulfate, filter the dried solution, spin-dry the solvent with a rotary evaporator to obtain a crude product.The crude product is separated and purified by silica gel chromatography column, the eluent is petroleum ether/dichloromethane mixed solvent,A white solid product was obtained with

61%

With tri-tert-butyl phosphine; palladium diacetate; sodium tertiary butoxide In toluene Inert atmosphere; Reflux;

1.3 Step 3: Synthesis of Intermediate 1e In a 250 ml reactor with a thermometer, stirring, and nitrogen protection, add dimethylacridine (6.6 g, 31.5 mmol), 1,4-dibromobenzene (11 g, 47 mmol), palladium acetate (0.4 g, 1.8 mmol) mmol), tri-tert-butylphosphine (2.7 g, 13.4 mmol), sodium tert-butoxide (4.5 g, 47 mol), and 130 ml of toluene, heat the reaction to reflux, and TLC detects that the reaction is complete. Filtration, spin-dried filtrate mixed with sample column chromatography, the developing solvent is petroleum ether, to obtain 7g of intermediate 1e, the yield is 61%.

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - CN105585577, 2016, A Location in patent: Paragraph 0122; 0123; 0124; 0125
[2]Current Patent Assignee: SOUTH CHINA COLLABORATIVE INNOVATION RES INSTITUTE - CN114409645, 2022, A Location in patent: Paragraph 0038-0042
[3]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN111675693, 2020, A Location in patent: Paragraph 0037-0042
[4]Current Patent Assignee: SUZHOU AOWEI PHOTOELECTRIC NEW MAT - CN113896723, 2022, A Location in patent: Paragraph 0031-0033; 0038-0039

7
[ 1342892-15-2 ]
[ 2417502-03-3 ]
[ 2417502-52-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate In toluene at 70 - 105℃; for 10h; Inert atmosphere; Reflux;	Under nitrogen protection, 35 mmol of intermediate 1, 35 mmol of intermediate 3, 160 mL of toluene, and 52.5 mmol of sodium tert-butoxide were added to the reaction flask, stirred and heated to 70-80 ° C, and then slowly added Pd2 (dba) 3 0.35 mmol and s-PHOS 0.70 mmol. After the addition was completed, the temperature was further raised to 100-105 ° C. and refluxed for 10 h. After the reaction was completed, the temperature was lowered and the mixture was extracted with dichloromethane. The organic phase was washed with water, dried, filtered, and concentrated. After passing through the column with a mixed solvent of dichloromethane and n-heptane, it was recrystallized to LC> 99.95%, and dried to obtain compound 2 (yield 65%).

Reference： [1]Current Patent Assignee: SHAANXI LIGHTE OPTOELECTRONICS MATERIAL CO.,LTD - CN110563647, 2019, A Location in patent: Paragraph 0079; 0080

8
[ 1342892-15-2 ]
[ 2586077-71-4 ]
[ 2586075-00-3 ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: 4-(4,6-diphenyl-1,3,5-triazin-2-yl)-1-methyl-4,9-dihydro-1H-pyrrolo[2,3-b]quinoxaline With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydroacridine In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere;	* Example 10-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)-1-methyl-1H-pyrrolo[2,3-b]quinoxalin-9(4H )-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine preparation (C-1) 500mlSodium hydride in a nitrogen atmosphere in a round bottom flask(60% mineral oil) (NaH) (0.8g, 22mmol) and 90.0ml of N,N-dimethylformamide were added and the reaction solution was cooled to 0. At 04-(4,6-diphenyl-1,3,5-triazin-2-yl)-1-methyl-4,9-dihydro-1H-pyrrolo[2,3-b]quinoxaline6.3g15mmol)After slowly adding the solution dissolved in 90.0 ml of N,N-dimethylformamide, the mixture was stirred at 0°C for 1 hour. 1 hour later10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydroacridine(6.6g, 18mmol) dissolved in 130ml of N,N-dimethylformamide was added slowly, and when completed, the reaction solution was raised to room temperature and stirred. When the reaction is complete, the reaction solution is poured into 1 L of water to precipitate a solid and then filtered. The solid was recrystallized using toluene and C-1(5.9g, 55.0%) was obtained.
55 %	Stage #1: 4-(4,6-diphenyl-1,3,5-triazin-2-yl)-1-methyl-4,9-dihydro-1H-pyrrolo[2,3-b]quinoxaline With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere; Stage #2: 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydroacridine In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere;	Preparation of 10-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)-1-methyl-1H-pyrrolo[2,3-b]quinoxalin-9(4H)-yl)phenyl)-9,9-dimethyl-9,10-dihydroacridine Sodium hydride (60% mineral oil) (NaH) (0.8g, 22mmol) and 90.0ml of N,N-dimethylformamide were put in a 500ml round bottom flask under a nitrogen atmosphere, and the reaction solution was cooled to 0°C.4-(4,6-diphenyl-1,3,5-triazin-2-yl)-1-methyl-4,9-dihydro-1H-pyrrolo[2,3-b]quinoxaline (6.3g, 15 mmol) in 90.0 ml of N, N-dimethylformamide was slowly added and stirred for 1 hour while maintaining 0 ° C.After 1 hour, a solution of 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydroacridine (6.6g, 18mmol) dissolved in 130ml of N,N-dimethylformamide was slowly added, and after completion, the reaction solution After raising to room temperature, stir.When the reaction is complete, the reaction solution is poured into 1 L of water to precipitate solids and then filtered.The solid was recrystallized using toluene to obtain C-1 (5.9g, 55.0%).

Reference： [1]Current Patent Assignee: CHOI, DON SOO - KR102201473, 2021, B1 Location in patent: Paragraph 0357-0360
[2]Current Patent Assignee: CHOI, Donsoo - WO2023/27220, 2023, A1 Location in patent: Paragraph 341-344

9
[ 1342892-15-2 ]
[ 2768956-67-6 ]
[ 2768956-61-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tripotassium phosphate tribasic; palladium diacetate; tricyclohexylphosphine tetrafluorohydroborate In toluene at 110℃; for 24h; Inert atmosphere;	12 (1) Synthesis of compound M12 Under nitrogen protection, compound U1 (10 mmol), 5,6-difluorosaccharin (10 mmol), palladium(II) acetate(1 mmol),Tricyclohexylphosphine (2 mmol) and tripotassium phosphate (15 mmol) were dissolved in 10 ml of toluene and heated to 110° C to react for 24 h. After the reaction was completed, it was cooled to room temperature, the product was extracted with ethyl acetate, washed three times with saturated aqueous sodium chloride solution, and after removing the organic solvent,The crude product petroleum ether:dichloromethane=3:2 (v/v) was used as the eluent for purification by column chromatography to obtain a solid product with a yield of 85%.The results of 1H NMR, 13CNMR, MS and elemental analysis indicated that the obtained compound was the target product.

Reference： [1]Current Patent Assignee: SOUTH CHINA COLLABORATIVE INNOVATION RES INSTITUTE - CN114409645, 2022, A Location in patent: Paragraph 0139-0143

10
[ 1342892-15-2 ]
[ 81-07-2 ]
[ 2768956-41-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With tripotassium phosphate tribasic; palladium diacetate; tricyclohexylphosphine tetrafluorohydroborate In toluene at 110℃; for 24h; Inert atmosphere;	1.2 (2) Synthesis of compound M1 Under nitrogen protection, compound U1 (10 mmol), saccharin (10 mmol), palladium(II) acetate(1 mmol),Tricyclohexylphosphine (2 mmol) and tripotassium phosphate (15 mmol) were dissolved in 10 ml of toluene and heated to 110° C to react for 24 h. After the reaction was completed, it was cooled to room temperature, the product was extracted with ethyl acetate, washed three times with saturated aqueous sodium chloride solution, and after removing the organic solvent,The crude product petroleum ether: dichloromethane=1:3 (v/v) was used as the eluent for purification by column chromatography to obtain a solid product with a yield of 81%.The results of 1H NMR, 13CNMR, MS and elemental analysis indicated that the obtained compound was the target product.

Reference： [1]Current Patent Assignee: SOUTH CHINA COLLABORATIVE INNOVATION RES INSTITUTE - CN114409645, 2022, A Location in patent: Paragraph 0038; 0043-0046

11
[ 1342892-15-2 ]
[ 2822671-36-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
77.3%	With 1,10-o-phenanthroline; potassium carbonate; copper(II) bromide In toluene at 110℃; for 8h;	1.7 (7) Synthesis of compound 42 Intermediate 42-1 can be obtained by referring to the synthesis method of intermediate 1-3 above. Add 10g of intermediate 2, 12.6g of intermediate 42-1, 7.8g of potassium carbonate, 200mL of toluene into the three-necked flask successively, pass nitrogen to replace the air in the reaction flask, add 0.41g of cuprous bromide, 0.52g of 1,10 - o-phenanthroline, the reaction solution was heated to 110°C under reflux and stirred for 8h. After cooling to room temperature, the reaction solution was washed with water until neutral, and the organic phase was dried with anhydrous sodium sulfate and purified by silica gel column to obtain 14.1 g of compound 42 with a yield of 77.3%.

Reference： [1]Current Patent Assignee: XI'AN MANARECO NEW MATERIALS CO LTD - CN114989170, 2022, A Location in patent: Paragraph 0034; 0069-0072

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Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1342892-15-2 ] {[proInfo.proName]}

Quality Control of [ 1342892-15-2 ]

Related Doc. of [ 1342892-15-2 ]

Product Details of [ 1342892-15-2 ]

Safety of [ 1342892-15-2 ]

Application In Synthesis of [ 1342892-15-2 ]

[ 1342892-15-2 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 1342892-15-2 ]

Aryls

Bromides

Related Parent Nucleus of [ 1342892-15-2 ]

Other Aromatic Heterocycles

Acridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1342892-15-2 ]

Related Parent Nucleus of
[ 1342892-15-2 ]