[ CAS No. 601454-33-5 ] {[proInfo.proName]}

Name: 601454-33-5|9-(4-Bromophenyl)-3,6-di-tert-butyl-9H-carbazole|97%
Brand: Ambeed
SKU: A363941
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2D 3D

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Quality Control of [ 601454-33-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 601454-33-5 ]

Product Details of [ 601454-33-5 ]

CAS No. :	601454-33-5	MDL No. :	MFCD11617971
Formula :	C₂₆H₂₈BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LAHSPJHDQUQBTB-UHFFFAOYSA-N
M.W :	434.41	Pubchem ID :	57604191
Synonyms :

Calculated chemistry of [ 601454-33-5 ]

Physicochemical Properties

Num. heavy atoms :	28
Num. arom. heavy atoms :	19
Fraction Csp3 :	0.31
Num. rotatable bonds :	3
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	127.02
TPSA :	4.93 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-2.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.89
Log Po/w (XLOGP3) :	9.03
Log Po/w (WLOGP) :	8.14
Log Po/w (MLOGP) :	6.7
Log Po/w (SILICOS-IT) :	7.4
Consensus Log Po/w :	7.23

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-8.53
Solubility :	0.00000129 mg/ml ; 0.000000003 mol/l
Class :	Poorly soluble
Log S (Ali) :	-9.03
Solubility :	0.00000041 mg/ml ; 0.0000000009 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-9.81
Solubility :	0.0000000668 mg/ml ; 0.0000000002 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.63

Safety of [ 601454-33-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 601454-33-5 ]

* 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.

Upstream synthesis route of [ 601454-33-5 ]
Downstream synthetic route of [ 601454-33-5 ]

[ 601454-33-5 ] Synthesis Path-Upstream 1~4

1
[ 37500-95-1 ]
[ 460-00-4 ]
[ 601454-33-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With caesium carbonate In N,N-dimethyl-formamide at 150℃; for 24 h;	General procedure: A mixture of a fluorinated aryl halide (2.0 mmol), a carbazole (0.5 mmol), and a base (2.0 mmol) in solvent (2 mL) was allowed to react under air atmosphere. The reaction mixture was heated to the specified temperature for 24 h. After reaction completion, the mixture was added to brine (15 mL) and extracted with CH₂Cl₂ (3 × 15 mL). The combined extract was concentrated under reduced pressure and the product was isolated by short chromatography on a silica gel (200–300 mesh) column.

Reference： [1] Synthesis (Germany), 2016, vol. 48, # 5, p. 737 - 750

2
[ 106-37-6 ]
[ 37500-95-1 ]
[ 601454-33-5 ]

Reference： [1] Chemistry Letters, 2008, vol. 37, # 9, p. 986 - 987
[2] Journal of the American Chemical Society, 2006, vol. 128, # 17, p. 5592 - 5593
[3] Organic Electronics: physics, materials, applications, 2012, vol. 13, # 1, p. 43 - 52
[4] Journal of Materials Chemistry C, 2015, vol. 3, # 4, p. 861 - 869
[5] Journal of Materials Chemistry C, 2017, vol. 5, # 37, p. 9753 - 9760
[6] Tetrahedron Letters, 2003, vol. 44, # 5, p. 957 - 959
[7] Journal of Physical Chemistry A, 2010, vol. 114, # 13, p. 4542 - 4549
[8] Organic Letters, 2014, vol. 16, # 20, p. 5346 - 5349
[9] Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18070 - 18081

3
[ 589-87-7 ]
[ 37500-95-1 ]
[ 601454-33-5 ]

Reference： [1] RSC Advances, 2015, vol. 5, # 64, p. 51512 - 51523
[2] Organic Electronics: physics, materials, applications, 2016, vol. 37, p. 14 - 23
[3] Journal of Materials Chemistry, 2012, vol. 22, # 37, p. 19700 - 19708,9
[4] Journal of Materials Chemistry, 2012, vol. 22, # 37, p. 19700 - 19708
[5] Dalton Transactions, 2014, vol. 43, # 47, p. 17624 - 17634
[6] Turkish Journal of Chemistry, 2015, vol. 39, # 5, p. 917 - 929

4
[ 86-74-8 ]
[ 601454-33-5 ]

Reference： [1] Organic Electronics: physics, materials, applications, 2012, vol. 13, # 1, p. 43 - 52
[2] Organic Letters, 2014, vol. 16, # 20, p. 5346 - 5349
[3] Turkish Journal of Chemistry, 2015, vol. 39, # 5, p. 917 - 929

[ 601454-33-5 ] Synthesis Path-Downstream 1~9

1
[ 61676-62-8 ]
[ 601454-33-5 ]
[ 764710-77-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 9-(4-bromophenyl)-3,6-bis(1,1-dimethylethyl)-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃; for 12h;	2 Synthesis of 2-B: Add 2-Br (2.01 g, 4.63 mmol, 1.0 equivalent) into a dry three-necked flask equipped with magnetic stirring.Purge nitrogen for three times, then add tetrahydrofuran (50mL) under nitrogen protection, cool the mixture to -78°C and slowly add n-butyllithium (2.89mL, 4.63mmol, 1.0 equivalent, 1.6mol/L hexane solution) dropwise , Stir at this temperature for 1 hour.Then the mixture was warmed to room temperature, and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (0.94mL, 4.63mmol , 1.0 equivalent) was added to the flask, and after stirring for 12 hours, the reaction was monitored by thin layer chromatography until the reaction was completed.The resulting mixture was cooled to room temperature and quenched with saturated ammonium chloride solution.The mixture was extracted three times with dichloromethane.
80%	Stage #1: 9-(4-bromophenyl)-3,6-bis(1,1-dimethylethyl)-9H-carbazole With n-butyllithium at -78℃; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane at -78 - 20℃;
	With n-butyllithium In tetrahydrofuran at -78℃; for 24h;

Stage #1: 9-(4-bromophenyl)-3,6-bis(1,1-dimethylethyl)-9H-carbazole With n-butyllithium at -78℃; for 1h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Reference： [1]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN111471043, 2020, A Location in patent: Paragraph 0060-0061; 0063
[2]Location in patent: scheme or table Lai, Wen-Yong; He, Qi-Yuan; Chen, Dao-Yong; Huang, Wei [Chemistry Letters, 2008, vol. 37, # 9, p. 986 - 987]
[3]He, Xuehan; Chen, Lei; Zhao, Yongbiao; Chen, Hui; Ng, Siu Choon; Wang, Xizu; Sun, Xiaowei; Matthew Hu, Xiao [Organic electronics, 2016, vol. 37, p. 14 - 23]
[4]Current Patent Assignee: UNIVERSITY OF WASHINGTON - WO2020/60937, 2020, A1 Location in patent: Sheet 25/94

2
[ 589-87-7 ]
[ 37500-95-1 ]
[ 601454-33-5 ]

Yield	Reaction Conditions	Operation in experiment
86.8%	With copper (I) iodide; potassium carbonate In N,N-dimethyl-formamide at 140℃; for 12h;	1.3 In the third step, a 250 ml two-necked flask was charged with 5.58 g (20 mmol) of 3,6-di-tert-butylcarbazole and 5.66 g (20 mmol) of 4-bromo-iodobenzene.Potassium carbonate 8.25g,Cuprous iodide 0.57 g and 140 ml of DMF.Reaction at 140 ° C for 12 h,After completion of the reaction, the mixture was cooled to room temperature, and a 2 mol/L dilute hydrochloric acid solution was added to the reaction mixture until neutral.The mixture was extracted with methylene chloride, and then filtered and evaporated. Separation by column chromatography,Target component were combined and concentrated to give a white solid 7.61g, yield 86.80%.
83%	With tripotassium phosphate tribasic; copper (I) iodide; trans-1,2-Diaminocyclohexane In toluene for 16h; Reflux; Inert atmosphere;	2.4.2. 9-(4-Bromophenyl)-3,6-di-tert-butylcarbazole (2) A mixture of CuI (0.7 g, 3.6 mmol), dried K3PO4 (3.8 g, 18.0 mmol),3,6-di-tert-butylcarbazole [43] (1.0 g, 3.6 mmol), 1-bromo-4-iodobenzene(1.5 g, 5.4 mmol) and (±)-trans-1,2-diaminocyclohexane (0.4 ml,3.6 mmol) in toluene (30 ml) was degassed with N2 for 10 min. Thereaction mixture was stirred and heated at refllux for 16 h. After beingcooled to room temperature, the crude reaction was filtered through aCelite pad eluting with dichloromethane, followed by concentrated invacuo. The crude product was purified by column chromatography onsilica gel eluting with hexane to give white solids (1.30 g, 83%). 1H NMR(600 MHz, CDCl3) 8.13 (2H, d, J = 1.9 Hz, Ar-H), 7.70 (2H, d, J = 8.6Hz, Ar-H), 7.48-7.42 (4H, m, Ar-H), 7.31 (2H, d, J = 8.5 Hz, Ar-H),1.47 (18H, s, C(CH3)3); 13C NMR (151 MHz, CDCl3) 143.2, 139.0,137.3, 133.0, 128.3, 123.7, 123.5, 120.3, 116.3, 109.0, 34.8, 32.0;HRMS APCI m/z cladc for C26H28BrN 433.1405; found 435.7320 M +H]+.
76%	With copper oxide (I); 2,2,6,6-tetramethylheptane-3,5-dione; potassium hydroxide In N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere; Schlenk technique;

75%	With tripotassium phosphate tribasic; copper (I) iodide; (±)-trans-1,2-diaminocyclohexane In toluene for 24h; Inert atmosphere; Reflux;	9-(4-Bromophenyl)-3,6-di-tert-butyl-9H-carbazole (4) : To a stirred solution of 2 (2.00 g, 7.16mmol), 1-bromo-4-iodobenzene (1) (2.23 g, 7.87 mmol), K3PO4 (1.90 g, 8.95 mmol), and CuI (0.68 g,3.58 mmol) in toluene (100 mL) was added ±trans-1,2-diaminocyclohexane (1 mL). The mixture wasrefluxed under N2 atmosphere for 24 hr. After cooling down to room temperature, the mixture waspoured into DI water and extracted three times with CH2Cl2. The combined organic layer was driedover Na2SO4, evaporated to dryness and purified by silica gel column chromatography using 10%CH2Cl2/hexane as eluent to yield white solids (2.34 g, 75%): 1H NMR (600 MHz, CDCl3) δ 8.04 (s,2H), 7.57 (d, J = 8.5 Hz, 2H), 7.35 (dd, J = 8.6, 1.1 Hz, 2H), 7.32 (d, J = 8.5 Hz, 2H), 7.20 (d, J = 8.6Hz, 2H), 1.37 (s, 18H); 13C NMR (151 MHz, CDCl3) δ 143.22, 138.99, 137.33, 133.02, 128.33, 123.79,123.54, 120.31, 116.38, 109.04, 34.79, 32.05; MALDI-TOF m/z [M - Br]+ calcd for C26H28N 355.2255,found 355.3865.
67%	With copper (I) iodide; potassium carbonate; <i>L</i>-proline In dimethyl sulfoxide at 100℃; for 36h; Inert atmosphere;	2 Synthesis of 2-Br: 3,6-di-tert-butylcarbazole (3.19g, 11.41mmol, 1.0 equivalent), 1-bromo-4-iodobenzene (3.55g, 12.55mmol, 1.1 equivalent), iodide Copper (217.2mg, 1.14mmol, 0.1 equivalent), L-proline (262.6mg, 2.28mmol, 0.2 equivalent) and potassium carbonate (2.63g, 22.81mmol, 2.0 equivalent) were added to a dry three-necked flask equipped with magnetic stirring. in.The nitrogen was pumped three times, and then dimethyl sulfoxide (60 mL) was added under the protection of nitrogen. The mixture was placed in an oil bath and heated to 100°C for reaction.After 36 hours, the reaction was monitored by thin layer chromatography until the reaction was complete.The resulting mixture was cooled to room temperature and diluted with dichloromethane.The mixture was washed three times with brine and extracted three times with dichloromethane.The combined organic layer was dried over anhydrous sodium sulfate and filtered.The filtrate was concentrated under reduced pressure, and the sample was purified by silica gel column chromatography (eluent: petroleum ether) to obtain 3.32 g of white solid with a yield of 67%
61%	With 1,10-Phenanthroline; copper chloride (I); potassium hydroxide In toluene for 24h; Reflux;
	With 18-crown-6 ether; copper atom; potassium carbonate In N,N-dimethyl-formamide Reflux;
	With 18-crown-6 ether; copper atom; potassium carbonate Inert atmosphere;
	With copper (I) iodide; potassium carbonate In N,N-dimethyl-formamide
	With copper (I) iodide; potassium carbonate In 1,2-dichloro-benzene Inert atmosphere;
	With 18-crown-6 ether; copper atom; potassium carbonate In nitrobenzene at 180℃; for 24h;

Reference： [1]Current Patent Assignee: TIANJIN UNIVERSITY - CN109879860, 2019, A Location in patent: Paragraph 0040-0041; 0045
[2]Chasing, Pongsakorn; Kaiyasuan, Chokchai; Namuangruk, Supawadee; Petdee, Sujinda; Promarak, Vinich; Sudyoadsuk, Taweesak; Therdkatanyuphong, Pattarawadee; Waengdongbung, Wijitra [Dyes and Pigments, 2021, vol. 195]
[3]Chen, Fei; Liu, Ning; Ji, Enhui; Dai, Bin [RSC Advances, 2015, vol. 5, # 64, p. 51512 - 51523]
[4]Chatsirisupachai, Jirat; Namuangrak, Supawadee; Promarak, Vinich; Sudyoadsuk, Taweesak [Synlett, 2022]
[5]Current Patent Assignee: ZHEJIANG UNIVERSITY OF TECHNOLOGY - CN111471043, 2020, A Location in patent: Paragraph 0060-0062
[6]He, Xuehan; Chen, Lei; Zhao, Yongbiao; Chen, Hui; Ng, Siu Choon; Wang, Xizu; Sun, Xiaowei; Matthew Hu, Xiao [Organic electronics, 2016, vol. 37, p. 14 - 23]
[7]Lee, Sai-Ho; Chan, Chris Tsz-Leung; Wong, Keith Man-Chung; Lam, Wai Han; Kwok, Wai-Ming; Yam, Vivian Wing-Wah [Dalton Transactions, 2014, vol. 43, # 47, p. 17624 - 17634]
[8]Öner, Saliha; Öner, Ilker; Akdag, Haydar; Varlikli, Canan [Turkish Journal of Chemistry, 2015, vol. 39, # 5, p. 917 - 929]
[9]Wu, Sen; Liu, Hongli; Sun, Wei; Li, Xianggao; Wang, Shirong [Organic electronics, 2019, vol. 71, p. 85 - 92]
[10]Deng, Lijun; Li, Jiuyan; Wang, Xinzeng; Zhang, Zhengchuan [Journal of Materials Chemistry, 2012, vol. 22, # 37, p. 19700 - 19708,9]
[11]Chen, Zhiyuan; Hu, Lai; Liu, Rui; Wang, Hongzhi; Zhu, Hongjun; Zhu, Senqiang [Inorganica Chimica Acta, 2022, vol. 531]

3
[ 73183-34-3 ]
[ 601454-33-5 ]
[ 764710-77-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 100℃; for 12h; Inert atmosphere;
77%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In toluene for 12h; Reflux; Inert atmosphere;	2.4.2. 9-(4-Bromophenyl)-3,6-di-tert-butylcarbazole (2) A mixture of CuI (0.7 g, 3.6 mmol), dried K3PO4 (3.8 g, 18.0 mmol),3,6-di-tert-butylcarbazole [43] (1.0 g, 3.6 mmol), 1-bromo-4-iodobenzene(1.5 g, 5.4 mmol) and (±)-trans-1,2-diaminocyclohexane (0.4 ml,3.6 mmol) in toluene (30 ml) was degassed with N2 for 10 min. Thereaction mixture was stirred and heated at refllux for 16 h. After beingcooled to room temperature, the crude reaction was filtered through aCelite pad eluting with dichloromethane, followed by concentrated invacuo. The crude product was purified by column chromatography onsilica gel eluting with hexane to give white solids (1.30 g, 83%). 1H NMR(600 MHz, CDCl3) 8.13 (2H, d, J = 1.9 Hz, Ar-H), 7.70 (2H, d, J = 8.6Hz, Ar-H), 7.48-7.42 (4H, m, Ar-H), 7.31 (2H, d, J = 8.5 Hz, Ar-H),1.47 (18H, s, C(CH3)3); 13C NMR (151 MHz, CDCl3) 143.2, 139.0,137.3, 133.0, 128.3, 123.7, 123.5, 120.3, 116.3, 109.0, 34.8, 32.0;HRMS APCI m/z cladc for C26H28BrN 433.1405; found 435.7320 M +H]+.
70%	With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In toluene for 24h; Reflux; Inert atmosphere;	3,6-Di-tert-butyl-9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole (6) : Toa mixture of 4 (1.00 g, 2.30 mmol), bis(pinacolato)diboron (1.46 g, 5.75 mmol), KOAc (1.36 g, 13.8mmol), and Pd(PPh3)2Cl2 (0.16 g, 0.23 mmol) was added toluene (100 mL). The mixture was refluxedunder N2 atmosphere for 24 hr. After cooling down to room temperature, the mixture was poured intoDI water and extracted three times with CH2Cl2. The combined organic layer was dried over Na2SO4,evaporated to dryness and purified by silica gel column chromatography using 50% CH2Cl2/hexane aseluent and recrystallized from CH2Cl2/MeOH to yield white solids (0.78 g, 70%): 1H NMR (600 MHz,CDCl3) δ 8.14 (s, 2H), 8.03 (d, J = 7.9 Hz, 2H), 7.59 (d, J = 7.9 Hz, 2H), 7.46 (d, J = 8.6 Hz, 2H), 7.39(d, J = 8.6 Hz, 2H), 1.47 (s, 18H), 1.40 (s, 12H); 13C NMR (151 MHz, CDCl3) δ 143.03, 140.91, 138.95,136.29, 125.65, 123.64, 123.56, 116.23, 109.32, 84.05, 46.10, 34.74, 32.02, 24.94; MALDI-TOF m/z[M]+ calcd for C32H40BNO2 481.3152, found 481.4666.

5.74 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 80℃; for 24h; Glovebox; Inert atmosphere;	6 Synthesis of intermediate D1Ph-B: D1Ph-Br (12.43 mmol, 5.4 g) was added to a single-necked flask.In a glove box, bis(pinacol) diboron (31.08 mmol, 7.89 g), Pd(dppf)Cl2 (0.25 mmol, 0.18 g) and KOAc (37.3 mmol, 3.66 g) were added.Add 30 mL of dry DMF under argon and stir in an oil bath at 80 ° C for 24 h.The solution turned black. Pour the reaction solution into water and filter by suction.The crude product was separated by column with 200-300 mesh silica gel as the stationary phase.Removal of unreacted raw materials with petroleum ether: CH2Cl2 = 4:1,Use petroleum ether: CH2Cl2 = 2:1 to flush the product,The white product 5.74 g was obtained as the intermediate D1Ph-B in a yield of 96.0%.
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In N,N-dimethyl-formamide at 100℃;
69 %	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane Inert atmosphere; Reflux;

Reference： [1]Yu, Mingquan; Wang, Shumeng; Shao, Shiyang; Ding, Junqiao; Wang, Lixiang; Jing, Xiabin; Wang, Fosong [Journal of Materials Chemistry C, 2015, vol. 3, # 4, p. 861 - 869] Zhao, Lei; Wang, Shumeng; Lü, Jianhong; Ding, Junqiao; Wang, Lixiang [Journal of Materials Chemistry C, 2017, vol. 5, # 37, p. 9753 - 9760]
[2]Chasing, Pongsakorn; Kaiyasuan, Chokchai; Namuangruk, Supawadee; Petdee, Sujinda; Promarak, Vinich; Sudyoadsuk, Taweesak; Therdkatanyuphong, Pattarawadee; Waengdongbung, Wijitra [Dyes and Pigments, 2021, vol. 195]
[3]Chatsirisupachai, Jirat; Sudyoadsuk, Taweesak; Namuangrak, Supawadee; Promarak, Vinich [Synlett, 2022, vol. 33, # 14, p. 1419 - 1425]
[4]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN108658948, 2018, A Location in patent: Paragraph 0135; 0136; 0139; 0140
[5]Chen, Jiangshan; Fröhlich, Johannes; Jin, Guangrong; Kader, Thomas; Kautny, Paul; Ma, Dongge; Pletzer, Matthias [Organic electronics, 2021, vol. 96]
[6]Wang, Xianhui; Liu, Zhangshan; Geng, Sinuo; Zhong, Ziting; Li, Huihui; Feng, Xin Jiang; Zhao, Zujin; Lu, Hua [Journal of Materials Chemistry C, 2023, vol. 11, # 16, p. 5316 - 5323]

4
[ 1231160-82-9 ]
[ 601454-33-5 ]
4-bromo triphenylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With C₁₁H₂₅PBF₄^(1-)H⁽¹⁺⁾; palladium diacetate; caesium carbonate; acetic acid In toluene at 100℃; for 12h; Schlenk technique; Inert atmosphere;

Reference： [1]Lin, Po-Han; Lu, Te-Jui; Cai, Deng-Jhou; Lee, Kun-Mu; Liu, Ching-Yuan [ChemSusChem, 2015, vol. 8, # 19, p. 3222 - 3227]

5
[ 37500-95-1 ]
[ 460-00-4 ]
[ 601454-33-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With caesium carbonate In N,N-dimethyl-formamide at 150℃; for 24h;	Metal-Free N-Arylation of Carbazoles; General Procedure General procedure: A mixture of a fluorinated aryl halide (2.0 mmol), a carbazole (0.5 mmol), and a base (2.0 mmol) in solvent (2 mL) was allowed to react under air atmosphere. The reaction mixture was heated to the specified temperature for 24 h. After reaction completion, the mixture was added to brine (15 mL) and extracted with CH2Cl2 (3 × 15 mL). The combined extract was concentrated under reduced pressure and the product was isolated by short chromatography on a silica gel (200-300 mesh) column.
	With caesium carbonate In N,N-dimethyl-formamide at 150℃;

Reference： [1]Wang, Lei; Ji, Enhui; Liu, Ning; Dai, Bin [Synthesis, 2016, vol. 48, # 5, p. 737 - 750]
[2]Chen, Jiangshan; Fröhlich, Johannes; Jin, Guangrong; Kader, Thomas; Kautny, Paul; Ma, Dongge; Pletzer, Matthias [Organic electronics, 2021, vol. 96]

6
[ 288-05-1 ]
[ 601454-33-5 ]
3,6-di-tert-butyl-9-[4-(selenophen-2-yl)phenyl]-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With palladium diacetate; potassium carbonate; catacxium A; Trimethylacetic acid In N,N-dimethyl-formamide at 110℃; for 12h; Schlenk technique; Inert atmosphere;

Reference： [1]Lu, Te-Jui; Lin, Po-Han; Lee, Kun-Mu; Liu, Ching-Yuan [European Journal of Organic Chemistry, 2017, vol. 2017, # 1, p. 111 - 123]

7
[ 255829-30-2 ]
[ 601454-33-5 ]
bis(4-(3,6-di-tert-butyl-9H-carbazol-9-yl)phenyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.41%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 36h;Inert atmosphere; Reflux;	the fourth step,Compound 3 2.85 g (6.6 mmol) was added to a 100 ml two-necked flask.Compound 2 3.00g (8.1mmol),Pd2(dba)3 0.25g,Sodium tert-butoxide 2.02g,2.8 ml of tri-tert-butyl phosphate and 50 ml of anhydrous toluene.The reaction was refluxed for 36h under argon protection condition,After the reaction was completed, it was washed three times with deionized water. The resulting organic phase was then dried to give a brown solid. The separation was carried out by column chromatography, and the title compound was concentrated to give a white solid 4.20 g, yield 82.41%.

Reference： [1]Patent: CN109879860,2019,A .Location in patent: Paragraph 0040-0041; 0046
[2]Organic electronics,2019,vol. 71,p. 85 - 92

8
[ 578-66-5 ]
[ 601454-33-5 ]
N,N-bis(4-(9H-3,6-di-tert-butylcarbazol-9-yl)phenyl)quinolin‐8‐amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With nickel(II) triflate; potassium carbonate In N,N-dimethyl acetamide at 100℃; for 24h; Inert atmosphere;	11; 12 Preparation Example 12 Add 1 magnetic stirrer, 8-aminoquinoline (0.3 mmol), 9-(4-bromophenyl)-3,6-di-tert-butylcarbazole (0.6 mmol), trifluoromethyl to a 10 mL reaction tube. Nickel sulfonate (0.03 mmol) and potassium carbonate (0.9 mmol) were vacuum-filled with nitrogen three times, and N,N-dimethylacetamide (2 mL) was added under a nitrogen atmosphere, and the mixture was reacted at 100 ° C for 24 hours.After the reaction is completed, it is quenched by the addition of saturated aqueous ammonium chloride solution, extracted with ethyl acetate, dried, concentrated, and then purified by column chromatography to obtain N,N-bis(4-(9H-3,6-di-tert-butylcarbazole). -9-yl)-phenyl)-8-aminoquinoline, yield 88%.
85%	With sodium hydroxide; nickel dichloride In N,N-dimethyl-formamide at 150℃; for 16h; Inert atmosphere; Glovebox; Sealed tube; Schlenk technique;

Reference： [1]Current Patent Assignee: HUNAN UNIVERSITY - CN110105337, 2019, A Location in patent: Paragraph 0036-0039
[2]Yan, Mingpan; Zhu, Longzhi; Zhang, Xingxing; Yin, Shuang-Feng; Kambe, Nobuaki; Qiu, Renhua [Organic Letters, 2021, vol. 23, # 7, p. 2514 - 2520]

9
[ 1219956-23-6 ]
[ 601454-33-5 ]
[ 2759143-37-6 ]

Yield	Reaction Conditions	Operation in experiment
78.07%	With tetrakis-(triphenylphosphine)-palladium; potassium carbonate In tetrahydrofuran; lithium hydroxide monohydrate at 80℃; for 12h; Inert atmosphere;	1.S2; 3.S2; 4.S2 S2. The intermediate m1 (521 mg, 1.20 mmol) obtained in step S1, 2,4-biphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxobrane-2-yl)phenyl)-1,3,5-triazine, tetras(triphenylphosphine)palladium, Potassium carbonate is added sequentially to a 25 mL round-bottom flask with a reflux condenser in a molar ratio of 1:1.05:047:2.51, the flask is vacuumed and replaced three times in dry nitrogen, and then 20 mL tetrahydrofuran and 1.2 mL deionized water are injected into the flask, reflux at nitrogen, 80 °C for 12 h, cooled, filtered, extracted with dichloromethane, isolated from the organic layer and dried with anhydrous magnesium sulfate, filtered and evaporated, and the crude product is passed by column chromatography (eluent is petroleum ether / Dichloromethane = 1:1 (v/v)) to give 621 mg of white powder (compound of formula (A1), yield of 78.07%).

Reference： [1]Current Patent Assignee: GUANGDONG UNIVERSITY OF TECHNOLOGY - CN113980002, 2022, A Location in patent: Paragraph 0092; 0096-0097; 0105; 0107; 0108; 0110

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