[ CAS No. 1533406-38-0 ] {[proInfo.proName]}

Name: 1533406-38-0|9-([1,1'-Biphenyl]-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole|97%
Brand: Ambeed
SKU: A146403
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Quality Control of [ 1533406-38-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1533406-38-0 ]

Product Details of [ 1533406-38-0 ]

CAS No. :	1533406-38-0	MDL No. :	MFCD28130384
Formula :	C₃₀H₂₈BNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VQLXKJLKLNGTQF-UHFFFAOYSA-N
M.W :	445.36	Pubchem ID :	90336757
Synonyms :

Calculated chemistry of [ 1533406-38-0 ]

Physicochemical Properties

Num. heavy atoms :	34
Num. arom. heavy atoms :	25
Fraction Csp3 :	0.2
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	142.69
TPSA :	23.39 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-3.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	7.61
Log Po/w (WLOGP) :	6.75
Log Po/w (MLOGP) :	4.9
Log Po/w (SILICOS-IT) :	5.52
Consensus Log Po/w :	4.96

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-7.74
Solubility :	0.00000807 mg/ml ; 0.0000000181 mol/l
Class :	Poorly soluble
Log S (Ali) :	-7.94
Solubility :	0.00000512 mg/ml ; 0.0000000115 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-10.65
Solubility :	0.0000000101 mg/ml ; 0.0 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.65

Safety of [ 1533406-38-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1533406-38-0 ]

* 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 [ 1533406-38-0 ]

[ 1533406-38-0 ] Synthesis Path-Downstream 1~25

1
[ 1533406-38-0 ]
[ 1926961-35-4 ]
[ 1926960-48-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water Reflux;	1 Preparation of the compound [220 General procedure: Intermediate in the reaction flask [29-5] 3g (5.8mmol), compound [9-6] 3.1g (6.95mmol), K2CO3 1.2g (8.69mmol), tetrakis (triphenylphosphine) palladium 0.2g (0.17mmol ), 10ml of distilled water, and stirred under reflux into a 100ml dioxane. After cooling to room temperature, filtered under reduced pressure after the completion of the reaction the resulting solid was washed with distilled water then recrystallized M.C to / Hex to produce a desired compound [29] 2.8g (71%). Intermediate compounds of Example 1, [29-1], [29-2], [29-3] Intermediate compound proceeds in the same manner as in Production Method [220-1], [220-3], [220-3] the production was, the compound [29] proceeds to the method of manufacturing the same manner to the target compound [220] was prepared.

Reference： [1]Current Patent Assignee: MBK CO.,LTD. - KR2016/49598, 2016, A Location in patent: Paragraph 0095; 0099; 0100-0102

2
[ 1533406-38-0 ]
[ 1210470-02-2 ]
[ 1926958-04-4 ]

Yield	Reaction Conditions	Operation in experiment
71%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water Reflux;	1 Preparation of the compound [29] Intermediate in the reaction flask [29-5] 3g (5.8mmol), compound [9-6] 3.1g (6.95mmol), K2CO3 1.2g (8.69mmol), tetrakis (triphenylphosphine) palladium 0.2g (0.17mmol ), 10ml of distilled water, and stirred under reflux into a 100ml dioxane. After cooling to room temperature, filtered under reduced pressure after the completion of the reaction the resulting solid was washed with distilled water then recrystallized M.C to / Hex to produce a desired compound [29] 2.8g (71%).

Reference： [1]Current Patent Assignee: MBK CO.,LTD. - KR2016/49598, 2016, A Location in patent: Paragraph 0081; 0082; 0083; 0094; 0095

3
[ 1533406-38-0 ]
[ 2075805-49-9 ]
[ 2075805-25-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 12h; Inert atmosphere; Reflux;	2 Synthesis Example 2: Synthesis of Compound S-5 500 mL round bottom of nitrogen environmentTo the flask was added Intermediate E 9.3 g(21.08 mmol), Intermediate G 11.26 g (25.29 mmol, Suzhou Rovathin), 5.826 g (42.15 mmol) of potassium carbonate, tetrakistriphenylphosphine palladium (0)1.22 g (1.05 mmol) was dissolved in 85 mL of tetrahydrofuranAnd distilled water (21 mL).The mixture was heated to reflux for 12 hours. Recrystallization from dichlorobenzene gave 10.8 g (76%) of the compound S-5.

Reference： [1]Current Patent Assignee: SAMSUNG SDI CO.,LTD. - KR2017/11338, 2017, A Location in patent: Paragraph 0291-0294

Yield	Reaction Conditions	Operation in experiment
90%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide for 5h; Inert atmosphere; Reflux;	18.3 Synthesis of Intermediate I-1 [Reaction Scheme 1] General procedure: In a nitrogen environment,100 g (326 mmol) of 2-bromo-trisbenzene (TCI) was dissolved in 1 L of dimethyl formamide (DMF)To this was added 99.2 g (391 mmol)Bis (pinacolato) diboron(Sigma - Aldrich Co., Ltd.),2.66 g (3.26 mmol) of (1,1'-bis (diphenylphosphino) dichloropalladium (II) and 80 g (815 mmol) of potassium acetate,And the mixture was heated and allowed to reflux at 150 ° C for 5 hours.When the reaction is complete,Water was added to the reaction solution,And the mixture is filtered and dried in a vacuum oven.The residue obtained is purified by column chromatography,113 g (98%) of compound I-1 were obtained.
61.1 %	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium acetate; XPhos In 1,4-dioxane at 110℃; Inert atmosphere;	General procedure: 3-Bromo-9-(9,9-dimethyl-9H-fluoren-2-yl)-9H-carbazole (10g, 22.8mmol) and bis(pinacolato)diboron (8.7g, 34.2mmol), tris(dibenzylideneacetone)dipalladium (0.21g, 0.22mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.22g, 0.46mmol), potassium acetate (3.4g, 34.2mmol) and 1,4-dioxane (100mL), heated to 110°C under nitrogen protection, heated to reflux and stirred for 5h. After the reaction solution was cooled to room temperature, the reaction solution was extracted with dichloromethane and water. The organic layer was dried over anhydrous magnesium sulfate and filtered. After filtration, the filtrate was passed through a short silica gel column, and the solvent was removed under reduced pressure. (1:3) system was used to recrystallize and purify the crude product to obtain intermediate S-1 (7.6 g, yield 68.6%).
68.1 %	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium acetate; XPhos In 1,4-dioxane at 80℃; Inert atmosphere;	33.1 General procedure: (5) Intermediate PT-68-4 (25g, 38.8mmol), pinacol borate (10.84g, 42.68mmol), tris(dibenzylideneacetone) dipalladium (0.36g, 0.39mmol), 2-Dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.37g, 0.78mmol) and potassium acetate (7.62g, 77.61mmol) were added to 1,4-dioxane (200mL ), heated to 80°C under the protection of nitrogen, and stirred for 3 hours; then cooled to room temperature, washed the reaction solution until neutral, combined the organic phases and dried them with anhydrous magnesium sulfate for 30 minutes, and filtered the filtrate to remove the solvent under reduced pressure; the obtained crude product was washed with acetic acid Ethyl ester/cyclohexane (volume ratio 1:1) was used to recrystallize and purify the crude product to obtain the intermediate PT-68-5 (20.7 g, yield 72.5%) as a pale yellow solid.

5
[ 894791-46-9 ]
9-(biphenyl-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole [ No CAS ]
9-([1,1'-biphenyl]-3-yl)-9’-([1,1'-biphenyl]-4-yl)-9H,9'H-3,3'-bicarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12h;Reflux;	10 g (34.83 mmol) of compound N,11.77 g (38.31 mmol)Of 9- [1,1'-biphenyl-4-yl] -3-bromo-9H-oxazole (TCI)14.44 g (104.49 mmol) of potassium carbonate and 0.80 g (0.7 mmol) of tetrakis- (triphenylphosphine) palladium (0) were suspended in 140 ml of toluene and 50 ml of distilled water,Then refluxed and stirred for 12 hours.Then,The resultant was recrystallized with methylene chloride and n-hexane,18.7 g (92%) of compound B-43.

Reference： [1]Patent: TW2016/15629,2016,A .Location in patent: Paragraph 0159; 0160

6
[ 1174032-81-5 ]
[ 1533406-38-0 ]
[ 2139242-82-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene for 12h; Reflux;	1.4 4) Production of H1-1 9 g (28 mmol) of the compound obtained in scheme 1c,13 g (28 mmol) of 2-bromoindolocarbazole, 2 g (1 mmol) of Pd (PPh3) 4 and 8 g (56 mmol) of potassium carbonate were suspended in 150 ml of toluene, 50 ml of ethyl alcohol and 50 ml of distilled water, Lt; / RTI & gt;The mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The reaction solution was refluxed under reduced pressure and then recrystallized to obtain 8 g (yield: 51%) of a compound H1-1. The NMR analysis results for the synthesized compound H1-1 are shown in Fig.

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2018/12499, 2018, A Location in patent: Paragraph 0182; 0195-0198

7
[ 1221237-87-1 ]
9-(biphenyl-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole [ No CAS ]

Reference： [1]Patent: KR2018/12499,2018,A
[2]Patent: KR2019/12678,2019,A
[3]Patent: US2019/378991,2019,A1

8
[ 1428551-28-3 ]
[ 73183-34-3 ]
[ 1533406-38-0 ]

Yield	Reaction Conditions	Operation in experiment
51%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane for 12h; Reflux;	1.3 3) Preparation of 9-(biphenyl-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 40 g (100 mmol) of the compound obtained in Scheme 1b, 38 g (151 mmol) of bis (pinacolato) diboron, 4 g (5 mmol) of Pd (dppf) Cl2 and 20 g mL, followed by reflux stirring for 12 hours. The mixture was extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration. The organic solution was removed and recrystallized to obtain 9-(biphenyl-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole 23g, 51%).
23 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane for 12h; Reflux;	1.3 Compound 9- (biphenyl-3-yl) -3-bromo-9H-carbazole 40g (100 mmol) Bis (pinacolato) diboron 38 g (151 mmol),[1,1'-Bis (diphenylphosphino) ferrocene] dichloropalladium (II)(5 mmol) of Pd (dppf) Cl2, 20 g (201 mmol) of potassium acetate,Was suspended in 1,4-dioxane (600 ml), and the mixture was refluxed for 12 hours.Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration.The organic solution was removed and recrystallized to obtain the compound9- (biphenyl-3-yl) -3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl) -9H-23g.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In tetrahydrofuran at 80℃; for 5h; Inert atmosphere;	11 In a 250 mL three-necked flask, nitrogen was passed through, 0.02 mol of raw material A-11 was added and dissolved in 100 mL of tetrahydrofuran (THF), and then 0.024 mol of raw material B,0.0002mol (1,1'-bis (diphenylphosphine) ferrocene) dichloropalladium (II) and 0.05mol potassium acetate were added, the mixture was stirred, and the mixed solution of the above reactants was heated to reflux at a reaction temperature of 80 ° C 5 hours; at the end of the reaction, cool and add 100 mL of water, and filter the mixture and dry in a vacuum oven. The obtained residue was separated and purified through a silica gel column to obtain intermediate M-11

2.84 g

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 85℃;

1-1.b Synthesis of intermediate DPhCZB The starting material BrPhCZ (3.22g, 10mmol), phenylboronic acid (1.34g, 11mmol),Tetratriphenylphosphine palladium (346mg, 0.3mmol) was sequentially added to a 250mL round bottom flask,After three times of pumping, use a syringe to inject degassed 60mL toluene, 30mL ethanol and 20mL 2M K2CO3 solution, and stir overnight at 90°C. After cooling to room temperature,Extract with dichloromethane, combine the organic phases and concentrate under reduced pressure,Column chromatography (mobile phase: petroleum ether/dichloromethane) was separated and purified to obtain DPhCZ (2.71 g, 85%). Then go directly to the next step, first add NBS (1.51g) at room temperatureBromination and purification by column chromatography to obtain the intermediate, which is thoroughly dried and placed in a 250 mL flask.Add potassium acetate (4.16g, 42.5mmol), Pd(dppf)Cl2 (187mg, 0.26mmol), Bpin 2 (2.38g, 9.35mmol),90 mL of 1,4-dioxane, stirring overnight at 85°C,After cooling, the organic solvent was removed under reduced pressure.Column chromatography was separated and purified to obtain another intermediate DPhCZB (2.84 g, yield 70%).

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2018/12499, 2018, A Location in patent: Paragraph 0182; 0191-0194
[2]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2019/12678, 2019, A Location in patent: Paragraph 0141; 0150-0153
[3]Current Patent Assignee: VALIANT CO., LTD. - CN110872286, 2020, A Location in patent: Paragraph 0128-0130
[4]Current Patent Assignee: CHANGZHOU TRONLY-ERAY OPTOELECTRONICS MATERIAL CO LTD; SHENZHEN UNIVERSITY - CN113121406, 2021, A Location in patent: Paragraph 0049; 0053-0055

9
[ 86-74-8 ]
[ 1533406-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / Reflux
	Multi-step reaction with 3 steps 1.1: copper; potassium carbonate; 18-crown-6 ether / 1,2-dichloro-benzene / 24 h / 150 °C / Inert atmosphere 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / Cooling with ice; Darkness 3.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 3.2: 12 h / -78 - 20 °C

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2019/12678, 2019, A
[2]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - US2019/378991, 2019, A1

10
[ 2113-57-7 ]
[ 1533406-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine / 5,5-dimethyl-1,3-cyclohexadiene / 12 h / Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / 20 °C 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / Reflux
	Multi-step reaction with 3 steps 1.1: copper; potassium carbonate; 18-crown-6 ether / 1,2-dichloro-benzene / 24 h / 150 °C / Inert atmosphere 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 12 h / Cooling with ice; Darkness 3.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 3.2: 12 h / -78 - 20 °C

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2019/12678, 2019, A
[2]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - US2019/378991, 2019, A1

11
[ 61676-62-8 ]
[ 1428551-28-3 ]
[ 1533406-38-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 9-([1,1′-biphenyl]-3-yl)-3-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 20℃; for 12h;	7 Compound (2-46-7) (31.5 g, 80 mmol) and 300 mL of anhydrous tetrahydrofuran were added to a 500 mL three-necked flask under nitrogen atmosphere, cooled to -78° C., and 85 mmol of n-butyllithium was slowly added dropwise, the solution was reacted for 2 hours, then 90 mmol of isopropoxyboronic acid pinacol ester was added one time to allow the reaction temperature to rise to room temperature naturally. The reaction was further performed for 12 hours and then quenched by the addition of pure water. The reaction solution was rotary evaporated to remove most of the solvent, and then extracted with dichloromethane and washed with water for 3 times. The organic phase was collected, spin dried, and then recrystallized, with a yield of 90%.
90%	Stage #1: 9-([1,1′-biphenyl]-3-yl)-3-bromo-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;	10.3 Compound 2-39-3 (31.5 g, 80 mmol) and 300 mL of anhydrous tetrahydrofuran were added to a 500 mL three-necked flask under nitrogen atmosphere, cooled to -78° C., and 85 mmol of n-butyllithium was slowly added dropwise, the solution was reacted for 2 hours, then 90 mmol of isopropoxyboronic acid pinacol ester was added one time, and the reaction temperature was raised to room temperature naturally. The reaction was further performed for 12 hours and then quenched by addition of pure water. The reaction solution was rotary evaporated to remove most of the solvent, and then extracted with dichloromethane and washed with water for 3 times. The organic phase was collected, rotary evaporated dried, and then recrystallized, with a yield of 90%.
	With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere;	6 Intermediate 26 synthesis: under the environment of nitrogen, will (31.5 g, 80 mmol) of compound 2 - 39 - 3 and 300 ml anhydrous tetrahydrofuran is added to a 500 ml three-opening in the bottle, lowering the temperature to -78 °C, slowly dropping 85 mmol n-BuLi, reaction 2 hours, disposable injection 90 mmol isopropyl alcohol [...] borate, make reaction natural to rise to room temperature, to continue the reaction 12 hours, into pure water quenching reaction, turns on lathe after the majority of the solvent, dichloromethane is used for extraction and washing 3 times, the collection of organic phase, turns on lathe does recrystallization, yield 90%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - US2019/378991, 2019, A1 Location in patent: Paragraph 0203; 0204
[2]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - US2020/317646, 2020, A1 Location in patent: Paragraph 0228; 0231
[3]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN109705107, 2019, A Location in patent: Paragraph 0299; 0300; 0303

12
[ 1210469-11-6 ]
[ 1533406-38-0 ]
[ 2351888-23-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide; sodium hydroxide In water; toluene at 80℃; for 12h; Inert atmosphere;	6 Comp 6 synthesis: under the environment of nitrogen, will (8.9 g, 20 mmol) of compound 24 and (7.4 g, 20 mmol) of compound 26, (1.15 g, 1 mmol) four (triphenyl phosphate) palladium, (2.6 g, 8 mmol) tetrabutyl ammonium bromide, (3.2 g, 80 mmol) sodium hydroxide, (10 ml) and water (100 ml) toluene by adding 250 ml of bottle in three, heating 80 °C stirring for 12 hours, the end of the reaction, the reaction liquid rotary evaporate most of the solvent, dichloromethane is used for dissolving water washing 3 times, to collect organic the fluid mixes silica gel column purification, yield 80%.
80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide; sodium hydroxide In water; toluene at 80℃; for 12h; Inert atmosphere;	10.4 Compound 2-42-5 (8.9 g, 20 mmol) and compound 2-42-4 (7.4 g, 20 mmol), tetrakis(triphenylphosphine)palladium (1.15 g, 1 mmol), tetrabutylammonium bromide (2.6 g, 8 mmol), sodium hydroxide (3.2 g, 80 mmol), water (10 mL), and toluene (100 mL) were added to a 250 mL three-necked flask under nitrogen atmosphere, and the solution was heated to 80° C. and reacted under stirring for 12 hours, and then the reaction was ended. The reaction solution was rotary evaporated to remove most of the solvent, and then dissolved with dichloromethane and washed with water for 3 times. The organic solution was collected, mixed with silica gel, and then purified by column chromatography, with a yield of 80%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN109705107, 2019, A Location in patent: Paragraph 0299; 0300; 0304
[2]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - US2020/317646, 2020, A1 Location in patent: Paragraph 0228; 0232

13
[ 1533406-38-0 ]
[ 2227262-08-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; toluene / 12 h / 80 °C / Inert atmosphere 2: triethyl phosphite / 12 h / 190 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide; sodium hydroxide / water; toluene / 12 h / 80 °C / Inert atmosphere 2: triethyl phosphite / 12 h / 190 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - US2019/378991, 2019, A1
[2]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - US2020/317646, 2020, A1

14
[ 1533406-38-0 ]
[ 2088464-39-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrabutylammomium bromide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; toluene / 12 h / 80 °C / Inert atmosphere 2: triethyl phosphite / 12 h / 190 °C / Inert atmosphere 3: copper; potassium carbonate; 18-crown-6 ether / 1,2-dichloro-benzene / 24 h / 150 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - US2019/378991, 2019, A1

15
[ 577-19-5 ]
[ 1533406-38-0 ]
[ 2173057-10-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide; sodium hydroxide In water; toluene at 80℃; for 12h; Inert atmosphere;	7 Compound 2-92-1 (26.7 g, 60 mmol) and Compound 2-92-2 (12.1 g, 60 mmol), tetrakis(triphenylphosphine)palladium (3.45 g, 3 mmol), tetrabutylammonium bromide (7.8 g, 24 mmol), sodium hydroxide (4.8 g, 120 mmol), water (15 mL) and toluene (120 mL) were added to a 250 mL three-necked flask under nitrogen atmosphere, and the solution was heated to 80° C. and reacted under stirring for 12 hours, and then the reaction was ended. The reaction solution was rotary evaporated to remove most of the solvent, and then dissolved with dichloromethane and washed with water for 3 times. The organic solution was collected, mixed with silica gel, and then purified by column chromatography, with a yield of 80%.
80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide; sodium hydroxide In water; toluene at 80℃; for 12h; Inert atmosphere;	21.1 1) Synthesis of Intermediate 4-89-3: According to the synthesis method of compound 1-3-3, (44.5 g, 100 mmol) of compound 4-89-1 and (20.2 g, 100 mmol) of compound 4-89-2 were substituted for compound 1-3-1 and compound 1- 3-2, the yield is 80%
80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide; sodium hydroxide In water; toluene at 80℃; for 12h; Inert atmosphere;	11.1 (11) Synthesis of Compound (2-86): Compound 2-42-5 (26.7 g, 60 mmol) and compound 2-86-1 (12.1 g, 60 mmol), tetrakis(triphenylphosphine)palladium (3.45 g, 3 mmol), tetrabutylammonium bromide (7.8 g, 24 mmol), sodium hydroxide (4.8 g, 120 mmol), water (15 mL), and toluene (120 mL) were added to a 250 mL three-necked flask under nitrogen atmosphere, and the solution was heated to 80° C. and reacted under stirring for 12 hours, and then the reaction was ended. The reaction solution was rotary evaporated to remove most of the solvent, and then dissolved with dichloromethane and washed with water for 3 times. The organic solution was collected, mixed with silica gel, and then purified by column chromatography, with a yield of 80%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - US2019/378991, 2019, A1 Location in patent: Paragraph 0205
[2]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN111848590, 2020, A Location in patent: Paragraph 0357-0361
[3]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - US2020/317646, 2020, A1 Location in patent: Paragraph 0233; 0234

16
[ 108-77-0 ]
[ 1533406-38-0 ]
[ 2332866-88-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; palladium diacetate In water; N,N-dimethyl-formamide at 150℃; for 10h; Inert atmosphere;	11 In a 250 mL three-necked flask, nitrogen gas was added, 0.02 mol of raw material C-2, 150 mL of DMF, 0.024 mol of intermediate M-11, and 0.0002 mol of palladium acetate were stirred, and then 0.03 mol of K3PO4 aqueous solution was added, heated to 150 ° C, and refluxed. After 10 hours, the sample was spotted and the reaction was complete. After leaving to cool, water was added, the mixture was filtered and dried in a vacuum oven, and the resulting residue was purified through a silica gel column to obtain intermediate N-11.

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN110872286, 2020, A Location in patent: Paragraph 0128; 0129; 0131

17
[ 1533406-38-0 ]
[ 2451410-88-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: palladium diacetate; potassium phosphate / N,N-dimethyl-formamide; water / 10 h / 150 °C / Inert atmosphere 2: palladium diacetate; potassium phosphate / N,N-dimethyl-formamide; water / 10 h / 150 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN110872286, 2020, A

18
[ 1533406-38-0 ]
[ 2351888-26-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide; sodium hydroxide / water; toluene / 12 h / 80 °C / Inert atmosphere 2: triethyl phosphite / 12 h / 190 °C / Inert atmosphere 3: copper(l) iodide; potassium carbonate; 18-crown-6 ether / 1,2-dichloro-benzene / 24 h / 150 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - US2020/317646, 2020, A1

19
[ 1592-95-6 ]
[ 1533406-38-0 ]
[ 1800580-10-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water for 8h; Inert atmosphere; Reflux;	10 Preparation 10: Preparation of compound PGH-1 In a three-necked flask, 3-bromo-9H-carbazole (10.0 g, 40.6 mmol) and intermediate a (19.0 g, 42.7 mmol) were dissolved in THF (400 ml), and K2CO3 (22.5 g, 162.5 mmol) was dissolved in water (200 ml). melted in Here, tetrakis(triphenylphosphine)palladium(0)(0.5 g, 0.4 mmol) was added, and the mixture was stirred for 8 hours under reflux conditions in an argon atmosphere. Upon completion of the reaction, after cooling to room temperature, the reaction solution was transferred to a separatory funnel and extracted with CH2Cl2. After drying the extract with MgSO4, filtration and concentration, the sample was purified by silica gel column chromatography to prepare 14.8 g of intermediate M1. (yield 75%, MS: [M+H]+= 484)

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2021/90468, 2021, A Location in patent: Paragraph 0295-0297

20
[ 1592-95-6 ]
[ 1533406-38-0 ]
[ 1352040-89-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran; water / 8 h / Inert atmosphere; Reflux 2: sodium t-butanolate; bis(tri-t-butylphosphine)palladium⁽⁰⁾ / toluene / 6 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2021/90468, 2021, A

21
[ 1533406-38-0 ]
[ 2677049-84-0 ]
[ 2677049-85-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 95 - 100℃;	1-1.c Synthesis of compound 2 Add equimolar amounts of intermediates DPhCZB (1.78g, 4mmol) and BrDPFCZ (2.56g, 4mmol), tetrakistriphenylphosphine palladium (138mg, 0.12mmol) into a 250mL flask in turn, pump through three times and then inject it with a syringe 50mL toluene,10mL ethanol and 10mL 2M K2CO3 solution were stirred overnight at 95-100°C. After cooling to room temperature, it was extracted with dichloromethane, and the combined organic phases were concentrated under reduced pressure.Then, it is separated and purified by column chromatography (mobile phase is petroleum ether/dichloromethane) to obtain the target product 2 (2.63 g, yield 75%). The initial product undergoes recrystallization,Sublimation to obtain high-purity compound 2 with a purity of 99.98%.

Reference： [1]Current Patent Assignee: CHANGZHOU TRONLY-ERAY OPTOELECTRONICS MATERIAL CO LTD; SHENZHEN UNIVERSITY - CN113121406, 2021, A Location in patent: Paragraph 0049; 0056-0061

22
[ 185112-61-2 ]
[ 1533406-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / toluene; ethanol; water / 90 °C 2: N-Bromosuccinimide / 20 °C 3: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 85 °C

Reference： [1]Current Patent Assignee: CHANGZHOU TRONLY-ERAY OPTOELECTRONICS MATERIAL CO LTD; SHENZHEN UNIVERSITY - CN113121406, 2021, A

23
[ 98-80-6 ]
[ 1533406-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / toluene; ethanol; water / 90 °C 2: N-Bromosuccinimide / 20 °C 3: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 85 °C

Reference： [1]Current Patent Assignee: CHANGZHOU TRONLY-ERAY OPTOELECTRONICS MATERIAL CO LTD; SHENZHEN UNIVERSITY - CN113121406, 2021, A

24
[ 1533406-38-0 ]
[ 2087889-98-1 ]
[ 2803718-51-4 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate; palladium In ethanol; water; toluene for 12h; Inert atmosphere; Reflux;	2 Preparation of compound CJHM515 (taking_T2as an example): 10.0mmol intermediates OA1, 12.0mmol of 9-(3-biphenyl)carbazole-3-boronic acid pinacol ester, 40.0mmol of anhydrous potassium carbonate and 0.1mmol of Pd132 dissolved in 40mL of toluene, 20mL of ethanol and 20mL of water, under nitrogen protection, warming reflux stirring reaction for 12 hours, reduced to room temperature, diluted with 50mL of water, extracted with dichloromethane, collected organic phase, dried, filtered, filtrate concentrated drying under reduced pressure, Separated and purified with a silica gel column, compound CJHM515, white solid, yield: 87%,

Reference： [1]Current Patent Assignee: SHANGHAI BAYI SPACE TIME ADVANCED MAT - CN113943279, 2022, A Location in patent: Paragraph 0113-0116

25
[ 1351870-13-7 ]
[ 1533406-38-0 ]
[ 1888438-12-7 ]

Yield	Reaction Conditions	Operation in experiment
83 %	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutylammomium bromide; sodium hydroxide In water; toluene at 80℃; Inert atmosphere;	26 2) Synthesis of intermediate 6-4-4 General procedure: under nitrogen atmosphere, (12g, 30mmol) compound 6-4-2 and (6.7g, 30mmol) compound 6-4-3, (1.72g, 1.5mmol ) tetrakis(triphenylphosphine)palladium, (1.3g, 4mmol) tetrabutylammonium bromide, (2g, 50mmol) sodium hydroxide, (20mL) water and (150mL) toluene add in the there-necked flask of 250mL,Heat at 80°C and stir for 12 hours to complete the reaction. Rotate the reaction solution to remove most of the solvent, wash it with dichloromethane dissolved water for 3 times, collect the organic liquid, and perform recrystallization and purification after rotary evaporation to obtain intermediate 6-4-4, yield 71%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN115611919, 2023, A Location in patent: Paragraph 0140-0142; 0144; 0267-0270

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[ 1533406-38-0 ]

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