Name: 400607-46-7|(10-(Naphthalen-1-yl)anthracen-9-yl)boronic acid|98%
Brand: Ambeed
SKU: A361073
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1
[ 400607-46-7 ]
[ 13720-06-4 ]
C₅₈H₃₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 12h;Heating / reflux;	Example 9 : Preparation of compound 19; [169] <n="71"/>HO OHBr19[170] Under N atmosphere, <strong>[13720-06-4]2,6-dibromonaphthalene</strong> (1.5 g, 5.2 mmol), ltheta-(l-naphthyl) anthracene-9-boronic acid (4.0 g, 11.4 mmol), and Pd(PPh ) (0.3 g, 0.26 mmol) were3 4 added to a 2 M aqueous solution of potassium carbonate (80 mL) and anisole (100 mL). The mixture was refluxed under stirring for about 12 hours. After completing the reaction, the mixture was cooled to normal temperature. The organic layer was separated from the reaction mixture, and filtered to obtain a solid. The solid was re- crystallized from THF and EtOH to prepare a compound 19 (2.9 g, 78%). MS [M+H] = 733

Reference： [1]Patent: WO2007/86695,2007,A1 .Location in patent: Page/Page column 68-69
[2]Patent: KR2020/53259,2020,A .Location in patent: Paragraph 0201-0203

2
[ 400607-46-7 ]
[ 83-53-4 ]
C₅₈H₃₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux;	Example 16 : Preparation of compound 35; [219][220] Under N atmosphere, 1,4-dibromonaphthalene (1.5 g, 5.2 mmol),10-(l-naphthyl)anthracene-9-boronic acid (4.0 g, 11.4 mmol), Pd(PPh ) (0.3 g, 0.263 4 mmol) were added to a 2 M aqueous solution of potassium carbonate (80 mL) and anisole (100 mL). The mixture was refluxed under stirring for about 24 hours. After completing the reaction, the mixture was cooled to normal temperature. The organic layer was separated from the reaction mixture, filtered to obtain a solid. The solid was recrystallized from THF and EtOH to prepare a compound 35(2.3 g, 63%). MS [M+H] = 733

Reference： [1]Patent: WO2007/86695,2007,A1 .Location in patent: Page/Page column 75

3
[ 400607-46-7 ]
[ 7351-74-8 ]
C₅₈H₃₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; methoxybenzene; for 24h;Heating / reflux;	Example 3 : Preparation of compound 3; [112][113] Under N atmosphere, <strong>[7351-74-8]1,5-<strong>[7351-74-8]dibromonaphthalene</strong></strong> (1.5 g, 5.2 mmol),10-(l-naphthyl)anthracene-9-boronic acid (4.0 g, 11.4 mmol), and Pd(PPh ) (0.3 g, 0.26 mmol) were added to a 2 M aqueous solution of potassium carbonate (80 mL) and anisole (100 mL). The mixture was refluxed under stirring for about 24 hours. After completing the reaction, the mixture was cooled to normal temperature. The organic layer was separated from the reaction mixture, and filtered to obtain a solid. The solid was recrystallized from THF and EtOH to prepare a compound 3 (2.3 g, 63%). MS [M+H] = 733

Reference： [1]Patent: WO2007/86695,2007,A1 .Location in patent: Page/Page column 31

4
[ 400607-46-7 ]
[ 212385-73-4 ]
[ 1310481-56-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene for 4h; Inert atmosphere; Reflux;

Reference： [1]Location in patent: experimental part Park, Jeong Keun; Lee, Kum Hee; Kang, Sunwoo; Lee, Jin Yong; Park, Jung Sun; Seo, Ji Hoon; Kim, Young Kwan; Yoon, Seung Soo [Organic electronics, 2010, vol. 11, # 5, p. 905 - 915]

5
[ 400607-46-7 ]
[ 1147081-43-3 ]
[ 1197175-60-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 24h;Inert atmosphere; Reflux; Darkness;	General procedure: A 100 ml two-neck round-bottomed flask was added compound 1 (0.90 g, 2 mmol), anthracen-9-ylboronic acid (0.49 g, 2.2 mmol), toluene (30 ml), ethanol (15 ml), 2 M K2CO3 (30 ml, 60 mmol) aqueous solution and tetrakis-(triphenylphosphine) palladium (0) (0.12 g, 0.1 mmol) in turn, then the reaction mixture was refluxed under nitrogen for 24 h in the absence of light. After the reaction was completed, cooled to room temperature. The solution was extracted with dichloromethane, dried by MgSO4. The organic layer was concentrated under a reduced pressure and purified by column chromatography and dried under vacuum to yield a white solid. Yield: 90%. 1H-NMR: (DMSO-d6, 400 MHz): δ (ppm) 8.95 - 8.93 (d, J = 8.0 Hz, 1H), 8.90 - 8.88 (d, J = 8.0 Hz, 1H), 8.79 - 8.76 (d, J = 8.0 Hz, 1H), 8.66 (s, 1H), 8.15 - 8.12 (d, J = 8.0 Hz, 2H), 7.84 - 7.77 (m, 5H), 7.76 - 7.68 (m, 4H), 7.59 - 7.46 (m, 5H), 7.44 - 7.33 (m, 5H), 7.15 - 7.13 (d, J = 8.0 Hz, 1H). MS (APCI) (m/z): [M+H+] calcd for C41H27N2, 547.7; found, 547.2. 13C NMR (100 MHz, DMSO-d6) δ (ppm) 150.68, 139.14, 138.75, 137.10, 135.92, 131.31, 131.25, 130.90, 130.81, 130.14, 129.79, 129.69, 129.60, 129.65, 128.94, 128.40, 128.23, 128.00, 127.25, 127.14, 126.46, 126.27, 126.23, 125.80, 125.75, 125.00, 124.17, 123.00, 122.53, 120.72. Anal. Calcd for C41H26N2: C, 90.08; H, 4.79; N, 5.12. Found: C, 89.90; H, 4.89; N, 5.21.

Reference： [1]Organic electronics,2012,vol. 13,p. 3050 - 3059

6
[ 400607-46-7 ]
[ 1121545-27-4 ]
[ 1584686-39-4 ]

Yield	Reaction Conditions	Operation in experiment
76%		General procedure: A solution of 3-bromospiro[benzo[de]anthracene-7,9′-fluorene] (4.51g, 10mmol), tetrakis(triphenylphosphine)palladium(0) (0.59 g, 0.51mmol), and <strong>[400607-46-7]10-(naphthalene-1-yl)anthracene-9-ylboronic acid</strong> (3.48 g, 10mmol) dissolved in THF (150 mL) was stirred in a double-necked flask for 30 min. Potassium carbonate (2 M, 150mL) was added dropwise over 20 min. The resulting reaction mixture was refluxed overnight at 80 C and then extracted with ethyl acetate and water. After the organic layer was evaporated with a rotary evaporator, the resulting powdery product was purified by column chromatography from dichloromethane/ n-hexane (1/1) to give the yellow NA-SBAF crystalline product. 3-[10-(naphthalene-1-yl)anthracene-9-yl]-1-methylspiro[benzo[de]anthracene-7,9′-fluorene] (NA-MSBAF) was prepared using similar procedures described above. NA-SBAF. Yield 76%. Mp 401C. FT-IR (KBr, cm-1) 3060, 3018 (aromatic-C-H). 1H NMR (500 MHz, CDCl3, ppm) 8.92-8.98 (m, 2H), 8.68 (d, J=5.0Hz, 1H), 6.70-8.06 (m, 29H). 13C NMR (500 MHz, CDCl3, ppm) 150.8, 148.6, 148.2, 147.6, 143.1, 142.5, 142.3, 140.2, 138.8, 137.5, 137.1, 136.9, 136.4, 135.2, 134.2, 133.9, 133.7, 133.3, 130.8, 129.8, 129.5, 129.2, 128.6, 128.2, 127.8, 127.6, 127.2, 127.2, 126.2, 125.9, 125.3, 125.0, 124.5, 124.0, 123.6, 123.2, 122.4, 120.5, 120.2, 66.5. MS (FAB) m/z 669 [(M+1)+]. Anal. Calcd. for C53H32 (668.82): C, 95.18; H, 4.82. Found: C, 95.09; H, 4.81. UV-vis (THF): λmax (Absorption)=376nm, λmax (Emission)=431 nm.

Reference： [1]Dyes and Pigments,2014,vol. 105,p. 202 - 207

7
[ 400607-46-7 ]
[ 1584686-38-3 ]
[ 1584686-40-7 ]

Yield	Reaction Conditions	Operation in experiment
72%		General procedure: A solution of 3-bromospiro[benzo[de]anthracene-7,9′-fluorene] (4.51g, 10mmol), tetrakis(triphenylphosphine)palladium(0) (0.59 g, 0.51mmol), and <strong>[400607-46-7]10-(naphthalene-1-yl)anthracene-9-ylboronic acid</strong> (3.48 g, 10mmol) dissolved in THF (150 mL) was stirred in a double-necked flask for 30 min. Potassium carbonate (2 M, 150mL) was added dropwise over 20 min. The resulting reaction mixture was refluxed overnight at 80 C and then extracted with ethyl acetate and water. After the organic layer was evaporated with a rotary evaporator, the resulting powdery product was purified by column chromatography from dichloromethane/ n-hexane (1/1) to give the yellow NA-SBAF crystalline product. 3-[10-(naphthalene-1-yl)anthracene-9-yl]-1-methylspiro[benzo[de]anthracene-7,9′-fluorene] (NA-MSBAF) was prepared using similar procedures described above.

Reference： [1]Dyes and Pigments,2014,vol. 105,p. 202 - 207

8
[ 400607-46-7 ]
[ 1430055-32-5 ]
[ 1430055-35-8 ]

Yield	Reaction Conditions	Operation in experiment
53.5%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 10.5h;Inert atmosphere; Reflux;	The above 5-bromo-2-{4-(pyridin-3-yl) phenyl}-2H-benzotriazole synthesized in Example 1 4.0 g, 10-(Naphthalen-1-yl)anthracen-9-ylboronic acid 4.8 g, 2M Potassium carbonate aqueous solution 17 ml, Toluene 28 ml, and Ethanol 7 ml, were put into the reaction vessel purged with nitrogen, and through which the nitrogen gas was flown for 60 minutes with stirring. [0104] Next, 0.7 g of the tetrakistriphenylphosphine palladium (0) was added thereto, and the mixture was heated and refluxed for 10.5 hours with stirring. The organic layer was picked up by the separating operation, concentrated under a reduced pressure and was refined by the column chromatography to obtain 3.5 g of a yellow powder of 5-{10-(naphthalen-1-yl)anthracen-9-yl)-2-{4-(pyridin-3-yl)phenyl}-2H-benzotriazole (compound 8) (yield, 53.5%). [0105] The obtained yellow powder was identified for its structure by the NMR. Fig. 3 shows the results of the 1H-NMR measurement. [0106] The following 26 signals of hydrogen were detected by the 1H-NMR (CDCl3). δ (ppm) = 8.98 (1H) 8.67 (1H) 8.59 (2H) 8.19 (2H) 8.09 (1H) 8.04 (1H) 8.00 (1H) 7.84 (1H) 7.80 (1H) 7.73 (1H) 7.61 (1H) 7.47 (4H) 7.35 (2H) 7.25 (7H)

Reference： [1]Patent: EP2767534,2014,A1 .Location in patent: Paragraph 0102-0106

9
[ 400607-46-7 ]
[ 1430055-37-0 ]
[ 1430055-36-9 ]

Yield	Reaction Conditions	Operation in experiment
44%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 8.5h;Inert atmosphere; Reflux;	The above 5-bromo-2-{3-(pyridin-3-yl) phenyl}-2H-benzotriazole 2.9 g, 10-(Naphthalen-1-yl)anthracen-9-ylboronic acid 3.5 g, 2M Potassium carbonate aqueous solution 12 ml, Toluene 20 ml, Ethanol 5 ml, and Tetrakistriphenylphosphine palladium (0) 0.5 g, were put into the reaction vessel purged with nitrogen, and were heated and refluxed for 8.5 hours with stirring. [0109] The organic layer was picked up by the separating operation, concentrated under a reduced pressure and was refined by the column chromatography to obtain 2. 1 g of a yellow powder of 5-{10-(naphthalen-1-yl)anthracen-9-yl}-2-{3-(pyridin-3-yl)phenyl}-2H-benzotriazole (compound 10) (yield, 44.0%). [0110] The obtained yellow powder was identified for its structure by the NMR. Fig. 4 shows the results of the 1H-NMR measurement. [0111] The following 26 signals of hydrogen were detected by the 1H-NMR (CDCl3). δ (ppm) = 9.02 (1H) 8.70 (2H) 8.51 (1H) 8.19 (1H) 8.06 (3H) 7.80 (2H) 7.73 (2H) 7.60 (2H) 7.49 (4H) 7.34 (2H) 7.23 (6H)

Reference： [1]Patent: EP2767534,2014,A1 .Location in patent: Paragraph 0107-0111

10
[ 400607-46-7 ]
[ 92-86-4 ]
[ 1002328-32-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 4h;Reflux;	General Procedure for the Suzuki Cross Coupling Reaction9-(1-naphthyl)anthracen-10-yl-boronic acid (2.4 mol)and the corresponding aryl bromides (1.0 mol), Pd(PPh34(0.04 mol), aqueous 2.0 M Na2CO3 (10.0 mol), ethanol,and toluene were mixed in a flask. The mixture wasrefluxed for 4 h. After the reaction was completed, waterwas added to quench the reaction. After cooling, the crudesolid was collected by filtration, washed with water andethanol. The product was purified recrystallization fromCH2Cl2/EtOH.

Reference： [1]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 5242 - 5245

11
[ 400607-46-7 ]
[ 28320-32-3 ]
10-(9,9-dimethyl-2-(10-(naphthalen-1-yl)anthracen-9-yl)-9H-fluoren-7-yl)-9-(naphthalen-1-yl)anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 4h;Reflux;	General Procedure for the Suzuki Cross Coupling Reaction9-(1-naphthyl)anthracen-10-yl-boronic acid (2.4 mol)and the corresponding aryl bromides (1.0 mol), Pd(PPh34(0.04 mol), aqueous 2.0 M Na2CO3 (10.0 mol), ethanol,and toluene were mixed in a flask. The mixture wasrefluxed for 4 h. After the reaction was completed, waterwas added to quench the reaction. After cooling, the crudesolid was collected by filtration, washed with water andethanol. The product was purified recrystallization fromCH2Cl2/EtOH.

Reference： [1]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 5242 - 5245

12
[ 400607-46-7 ]
[ 108-36-1 ]
1,3-bis(10-(naphthalen-1-yl)anthracen-9-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 4h;Reflux;	General Procedure for the Suzuki Cross Coupling Reaction9-(1-naphthyl)anthracen-10-yl-boronic acid (2.4 mol)and the corresponding aryl bromides (1.0 mol), Pd(PPh34(0.04 mol), aqueous 2.0 M Na2CO3 (10.0 mol), ethanol,and toluene were mixed in a flask. The mixture wasrefluxed for 4 h. After the reaction was completed, waterwas added to quench the reaction. After cooling, the crudesolid was collected by filtration, washed with water andethanol. The product was purified recrystallization fromCH2Cl2/EtOH. 2.1.1. 1,3-bis(10-(naphthalen-1-yl)anthracen-9-yl)Benzene (1)1H-NMR (500 MHz, CDCl3 [ ppm]: 8.06 (s, 8 H),8.01-7.92 (m, 3 H), 7.80-7.77 (m, 3 H), 7.72-7.68 (m,3 H), 7.62 (s, 1 H), 7.52-7.45 (m, 13 H), 7.14-7.05 (m,3 H). MS (APCI+) m/z 682 (M+).
6.5 g	With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); tetrabutylammomium bromide; potassium carbonate; In water; toluene; for 8h;Reflux; Inert atmosphere;	In a nitrogen atmosphere, a flask containing 1,3-dibromobenzene (3.0 g), (10-(1-naphthyl) anthracen-9-yl) boronic acid (9.7 g), Pd-132 (0.45 g), tetrabutylammonium bromide (0.41 g), potassium carbonate (5.3 g), water (10 ml), and toluene (100 ml) was stirred at a reflux temperature for eight hours. The reaction liquid was cooled to room temperature and subjected to liquid separation. The obtained organic layer was washed with water. This solution was decolorized using silica gel and concentrated under reduced pressure. The precipitated solid was washed with heptane to obtain compound (2A-45) (6.5 g). The structure of the compound thus obtained was identified by an NMR analysis. 1H-NMR (400 MHz, CDCl3):δ=8.10˜7.98 (m,7H), 7.96˜7.90 (m,1H), 7.84˜7.67 (m,4H), 7.65˜7.61 (m,1H), 7.55˜7.42 (m,10H), 7.30˜7.21 (m,8H), 7.20˜7.12 (m,2H), 7.08˜7.04 (m,1H).

Reference： [1]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 5242 - 5245
[2]Patent: US2019/312207,2019,A1 .Location in patent: Paragraph 0391-0394

13
[ 400607-46-7 ]
[ 106-37-6 ]
1,4-bis(9-(1-naphthyl)anthracene-10-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 4h;Reflux;	General Procedure for the Suzuki Cross Coupling Reaction9-(1-naphthyl)anthracen-10-yl-boronic acid (2.4 mol)and the corresponding aryl bromides (1.0 mol), Pd(PPh34(0.04 mol), aqueous 2.0 M Na2CO3 (10.0 mol), ethanol,and toluene were mixed in a flask. The mixture wasrefluxed for 4 h. After the reaction was completed, waterwas added to quench the reaction. After cooling, the crudesolid was collected by filtration, washed with water andethanol. The product was purified recrystallization fromCH2Cl2/EtOH.
74%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 4h;Inert atmosphere; Reflux;	General procedure: the corresponding 10-arylanthracen-9-yl-boronic acid; 10-phenylanthracen-9-ylboronic acid (1.52 g, 5.09 mmol),10-(1-naphthyl)anthracen-9-ylboronic acid or 10-(2-naphthyl)anthracen-9-ylboronic acid(1.77 g, 5.09 mmol) and 2,4-dibromobenzene (0.5 g, 2.12 mmol), Pd(PPh3)4 (980 mg,0.08 mmol), aqueous 2.0 M Na2CO3 (3.2 ml, 6.3 mmol), ethanol, and toluene were mixedin a flask under N2 gas. The mixture was refluxed for 4 h. After the reaction was completed,water was added to quench the reaction. After cooling, the crude solid was collected byfiltration, washed with water and ethanol. The product was purified recrystallization fromCH2Cl2/EtOH.

Reference： [1]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 5242 - 5245
[2]Molecular Crystals and Liquid Crystals,2014,vol. 601,p. 142 - 150

14
[ 474687-62-2 ]
[ 400607-46-7 ]
10-([naphthalen-1-yl]anthracen-9-yl)bispiro(9,10-dihydroanthracene-9,7′-7′H-fluorene-10,7″-7″H-fluorene) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 4h;Reflux;	General procedure: arylanthracenyl boronic acid such as 9-phenylanthracen-10-yl-10-boronic acid, 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid, and 9-(naphthalen-1-yl)anthracen-10-yl-10-boronic acid (1.2mol) and 2-bromo-bispiro(9,10-dihydro-anthracene-9,7′-7′H-fluorene-10,7″-7″H-fluorene) (1.0mol), Pd(PPh3)4 (0.04mol), aqueous 2.0M Na2CO3 (10.0mol), ethanol, and toluene were mixed in a flask. The mixture was refluxed for 4h. After the reaction was completed, water was added to quench the reaction. After cooling, the crude solid was collected by filtration, washed with water and ethanol. The product was purified recrystallization from CH2Cl2/EtOH. 1H NMR was recorded on a Varian Unity Inova 300Nb or Bruker Avance III 500MHz NMR spectrometer. FT-IR spectra were recorded using a Bruker VERTEX70 FT-IR spectrometer. Low-resolution mass spectra were measured using a Jeol JMS-600W spectrometer in the APCI mode. Elemental analyses (EA) were determined by a Flash 2000 autoanalyzer.

Reference： [1]Dyes and Pigments,2015,vol. 123,p. 363 - 369

15
[ 400607-46-7 ]
C₃₇H₂₂BrN [ No CAS ]
C₆₁H₃₇N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41.9%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene;Inert atmosphere; Reflux;	Pitching 25mL flask to intermediate (9) 500 mg (0.89 mmol), ((10 - (naphthalen-1-yl) anthracen-9-yl) boronic acid) 464 mg (1.34 mmol) and Pd (PPh3) 4 52 mg (0.045 mmol) and the mixture was dissolved in Toluene 6 mL EtOH and 3 mL under a nitrogen atmosphere, was added 0.89 mL of 2M Na2CO3 solution was stirred under reflux. After completion of the reaction, the reaction was cooled to room temperature and solids formed were filtered, washed with Toluene. This was filtered through silica gel and dissolved in Chloroform 300mL the obtained solid, and concentrated under reduced pressure, and then the filtrate was washed with 1 L Chloroform. The obtained compound was filtered and solidified by the addition of EtOAc to obtain a compound (5-59, KJ-07-05), 292 mg (yield: 41.9%) as a pale yellow solid was obtained.

Reference： [1]Patent: KR2015/137230,2015,A .Location in patent: Paragraph 0509; 0510; 0511; 0512; 0513; 0514

16
[ 400607-46-7 ]
C₃₇H₂₂BrN [ No CAS ]
C₆₁H₃₇N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene;Inert atmosphere; Reflux;	Pitching 100 mL 0.3 g intermediate (12) was charged to the flask (0.54 mmol), (10- naphthalene-1-carbonyl) anthracene-9-carbonyl) acid ((10- (naphthalen-1-yl) anthracen-9-yl ) boronic acid) 0.28 g (0.81 mmol) and Pd (PPh3) 4 31 mg (0.027 mmol) were placed in a nitrogen atmosphere under Toluene 4 mL with EtOH 2 mL for dissolution was then, 2M K2CO3 solution 0.5 mL was added and refluxed under stirring was . After completion of the reaction, the reaction was cooled to ambient temperature and H2O was added to 3 mL. Drying the mixture and then extracted two times with MC 20 mL extract with Na2SO4, filtered and concentrated under a reduced pressure. Purification of the resulting compound was purified by silica gel column chromatography to obtain the compound of yellow solid (5-78, HSB-08-001) 0.16 g (Yield: 38%) was obtained.

Reference： [1]Patent: KR2015/137230,2015,A .Location in patent: Paragraph 0601; 0602; 0603; 0604

17
[ 400607-46-7 ]
C₃₇H₂₂BrN [ No CAS ]
C₆₁H₃₇N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54.6%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene;Inert atmosphere; Reflux;	Pitching 25 mL intermediate (18) was charged to the flask 500 mg (0.89 mmol), (10- 1-yl) anthracene-9-yl) boronic acid ((10- (naphthalen-1-yl) anthracen-9-yl ) boronic acid) 373 mg (1.07 mmol) and Pd (PPh3) 4 52 mg (0.045 mmol) were placed in a nitrogen atmosphere under Toluene 6 mL with EtOH 3 mL for dissolution was then, 2M Na2CO3 solution, 0.89 mL was added and refluxed under stirring was . After completion of the reaction, the reaction was cooled to room temperature and added to 5 mL H2O. Drying the mixture and then extracted two times with MC 20 mL extract with Na2SO4, filtered and concentrated under a reduced pressure. Purification of the resulting compound was purified by silica gel column chromatography to obtain the compound (5-38, KJ-06-31), 381 mg (yield: 54.6%) of a yellow solid was obtained.

Reference： [1]Patent: KR2015/137230,2015,A .Location in patent: Paragraph 0395; 0396; 0397; 0398; 0399; 0400

18
[ 4373-72-2 ]
[ 400607-46-7 ]
[ 1379518-33-8 ]

Yield	Reaction Conditions	Operation in experiment
1.54 g	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In water; isopropyl alcohol for 10h; Inert atmosphere; Reflux;	10 4-(3-(10-(naphthalen-1-yl)anthracen-9-yl)phenyl)pyridine synthesis commercially available (10-(naphthalen-1-yl)anthracen-9-yl)boronic acid 2.78g, 4-(3-bromophenyl)pyridine 2.25g, tetrakis(triphenylphosphine)palladium(0) 0.28g, potassium phosphate 3.39g, pseudocumene 20 ml, isopropyl alcohol 4 ml, and 1 ml water placed in a flask, under nitrogen atmosphere, this mixture was stirred for 10 hours at reflux temperature. The reaction liquid to room temperature by cooling, and toluene liquid water addition. Solvent under a reduced pressure, a solid obtained by refining alumina column chromatography (soln.: toluene). A reduced pressure of solvent elution liquid, by recrystallization from toluene, 4-(3-(10-(naphthalen-1-yl)anthracen-9-yl)phenyl)pyridine (1.54g) is obtained.

Reference： [1]Current Patent Assignee: CHISSO CORPORATION - JP5907069, 2016, B2 Location in patent: Paragraph 0199

19
[ 39795-60-3 ]
[ 400607-46-7 ]
4-(4-(10-(naphthalen-1-yl)anthracen-9-yl)phenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.90 g	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; tert-butyl alcohol; for 16h;Inert atmosphere; Reflux;	commercially available (10-(naphthalen-1-yl)anthracen-9-yl)boronic acid 5.22g, <strong>[39795-60-3]4-(4-bromophenyl)pyridine</strong> 4.12g, tetrakis(triphenylphosphine)palladium(0) 0.52g, potassium phosphate 6.38g, pseudocumene 25 ml, t-butyl alcohol 5 ml, 1 ml of water is placed in a flask, under a nitrogen atmosphere this mixture was heated to reflux temperature for 16 hours . After cooling the reaction liquid to room temperature, washed with pure water. The reduced pressure solvent, silica gel chromatography (developing solvent: toluene-toluene/ethyl acetate = 9/1 (volume ratio)) is purified by, 4-(4-(10-(naphthalen-1-yl)anthracen-9-yl)phenyl)pyridine 3.90g is obtained.

Reference： [1]Patent: JP5907069,2016,B2 .Location in patent: Paragraph 0185

20
[ 5419-55-6 ]
[ 400607-04-7 ]
[ 400607-46-7 ]

Yield	Reaction Conditions	Operation in experiment
75%		In N2protection, ventilation after three times, the tetrahydrofuran solution (100 ml) and 9-bromo -10 - (1-naphthyl) anthracene (7.8g, 20 . 3mmol) is added to the three-hole bottle, to control the temperature to -78 C, begins to stir, 60 min after the n-BuLi (8.9 ml) in slowly dripped into the reaction bottle, to continue to maintain the above-mentioned temperature, the time when the white emulsion, stirring 60 min, triisopropyl instillment boric acid (4.58g, 24 . 4mmol) continue to stir 3 hours, recover to room temperature, the reaction continued at room temperature overnight, TLC for detecting the reaction progress.Processing process: TLC for tracking of the reaction process, determining after the reaction, acidized, water, liquid (the upper layer is the reaction solution in other words: tetrahydrofuran solution), the water layer is extracted with methylene chloride three times, the resulting solution is distilled using rotary evaporimeter, filters after adding petroleum ether to obtain white solid, the resulting white solid product in 50 C bake 3h, get D-1 (5.3g, 75%).

Reference： [1]Patent: CN105384613,2016,A .Location in patent: Paragraph 0047; 0048

21
[ 400607-46-7 ]
C₃₇H₂₂BrN [ No CAS ]
C₆₁H₃₇N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; for 24h;Reflux;	In the production example of the 1-1-25 of Preparation Example 1, 2- [9,10-di-2-naphthalenyl-2-anthracenyl] -4,4,5,5- tetrahydro-l, Bo is a 3,2- dioxa (2- [9,10-di-2-naphthalenyl-2-anthracenyl] -4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 9- instead (naphthalen-l - yl) anthracene -10 days -10-boronic acid (9 - (nap hthalen-1-yl) anthracen-10-yl-10-boronic acid, 8.7g, 5mmol) using the same method, except that It was reacted to prepare the compound 1-4-21 (15.5g, 79% yield)All.

Reference： [1]Patent: KR101550523,2015,B1 .Location in patent: Paragraph 0206-0208

22
[ 400607-46-7 ]
C₂₈H₁₆BrN [ No CAS ]
C₅₂H₃₁N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In tetrahydrofuran; water; for 24h;Reflux;	In the production example of the 1-1-25 of Preparation Example 1, 2- [9,10-di-2-naphthalenyl-2-anthracenyl] -4,4,5,5- tetrahydro-l, Bo is a 3,2- dioxa (2- [9,10-di-2-naphthalenyl-2-anthracenyl] -4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 9- instead (naphthalene-3-yl) anthracene-10-yl-10-boronic acid (9- (naphthalen-3-yl) anthracen-10-yl-10-boronic acid, 3.5g, 10.0mmol) and the same, except for using how to react the compound 1-5-1 (4.1g, yield 57%) was prepared.

Reference： [1]Patent: KR101550523,2015,B1 .Location in patent: Paragraph 0190-0192

23
[ 400607-46-7 ]
C₂₆H₁₅ClO [ No CAS ]
C₅₀H₃₀O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 4h;	Intermediate A-9 (3.79g, 10mmol), Intermediate B-4 (3.83g, 11mmol), Pd (PPh3) 4 (0.58 g, 0.5mmol), potassium carbonate (4.15g, 30mmol) and THF: H2O = 2: was dissolved in 1 200ml solution was stirred for 4 hours under reflux at 80 . After dried was added to 40ml H2O and the organic layer obtained by extraction three times with 40ml ethyl ether to remove the magnesium sulfate and the residue obtained by evaporating the solvent was subjected to silica gel column chromatography purification gave Compound 27 (5.48g, 85% yield) .

Reference： [1]Patent: KR2016/30001,2016,A .Location in patent: Paragraph 0341; 0347-0348

24
[ 121-43-7 ]
[ 400607-04-7 ]
[ 400607-46-7 ]

Yield	Reaction Conditions	Operation in experiment
86%		Under nitrogen, 3.83 g (10 mmol) of Intermediate-8 was dissolved in 40 ml of anhydrous THF, the temperature of the reaction was lowered to -78 C and 2.5 M n-After 4 ml of BuLi was slowly added dropwise, the reaction was stirred at 0 & lt; 0 & gt; C for 1 hour. Then, the temperature of the reactant was adjusted to -78 And 12.47 g (12 mmol) of trimethyl borate was added dropwise thereto, followed by stirring at room temperature for 12 hours. When the reaction is terminated2N-HCl aqueous solution was added thereto, stirred for 30 minutes, and extracted with ether.After the water in the organic layer was removed with anhydrous MgSO4 and the filtrate was subjected to filtration under reduced pressure, the organic solvent was concentrated to obtain the resulting compound. Hex: MC = 3:1 to obtain 2.99 g (86%) of Intermediate-11.
83%		The [Reaction Scheme 16] (50 g, 271 mmol), 500 mL of tetrahydrofuran gave put obtained is then cooled to from -78 under a nitrogen atmosphere. After 30 minutes was added dropwise slowly a 1.6 M n- butyllithium 203 mL (325 mmol) and stirred for 1 hour at -78 C. It was added dropwise at -78 C slowly trimethyl-borate (33.8 g, 325 mmol) andFor 2 hours at room temperatureAfter stirring the mixture was stirred into a 2 M aqueous solution of hydrochloric acid.Extracted with ethyl acetate and H2O and the organic layer was concentrated under reduced pressure. Recrystallization with heptane to give the 51 g. (Yield 83%)
83.8%		In a 2 L round bottom flask, 88 g (230 mmol) of 9-bromo-10- (1-naphthalene) anthracene and 700 mL of tetrahydrofuran were added, cooled to -78 C. while blowing nitrogen, and dissolved with stirring. 157.8 mL of 1.6 M n-BuLi was slowly dropped and stirred for 2 hours while maintaining the temperature, 39 mL of trimethylborate was dropped, the ice bath was removed, and the mixture was stirred at room temperature for one day. After completion of the reaction, 2M hydrochloric acid was added and stirred, followed by extraction with ethyl acetate and water. The organic layers were collected, concentrated, and crystallized with toluene. (67 g, 83.8%)

80%		Intermediate B-3 (3.83g, 10mmol) at -78 was dissolved in THF 80mln-BuLi 4mL (10mmol, 2.5M in hexane)It was added dropwise slowly.While maintaining the temperature and then stirred for 1 hour, and then added dropwise 1.15g trimethyl borate (11mmol) slowly, and stirred for 6 hours at room temperature.The reaction was terminated after drying the organic layer was added 40mL of water, obtained by extraction three times with ethyl ether 40ml magnesium sulfate, and separating the residue obtained by evaporating the solvent was subjected to silica gel column chromatography purificationTo give the intermediate 4-B (2.78g, 80% yield).
45%		In a 4-neck round-bottom flask, Intermediate 5-b 5 g (0.2 mol) and tetrahydrofuran (750 mL) were placed and maintained at -78 C. 1.6M n-BuLi (150 mL) was slowly added to the solution which was then stirred for 2 hrs. At the same temperature, B(OMe)3 was dropwise added. The temperature was elevated to room temperature before stirring for 12 hrs. After completion of the reaction, 2N HCl was added. The organic layer was separated, neutralized, and recrystallized in toluene to afford Intermediate 5-c (30 g, 45%).
45%		5 g (0.2 mol) of Intermediate 5-b and 750 mL of tetrahydrofuran were added to a four neck round bottom flask and then maintained at a temperature of -78 C. 150 mL of 1.6 M n-BuLi was slowly added in a drop-wise manner to the flask, agitated for 2 hours, and then B(OMe)3 was added thereto in a drop-wise manner at the same temperature. The temperature was increased to room temperature and then the resultant was agitated for 12 hours. After agitating for 12 hours (or after completing the reaction), 2 N HCl was added thereto. An organic layer was separated therefrom, neutralized, and then recrystallized with toluene to obtain Intermediate 5-c (30 g, 45%).

Reference： [1]Patent: KR2017/49295,2017,A .Location in patent: Paragraph 0179-0183
[2]Patent: KR2016/90242,2016,A .Location in patent: Paragraph 0272; 0273; 0274; 0275; 0276; 0277
[3]Patent: KR102017506,2019,B1 .Location in patent: Paragraph 0252; 0259-0261
[4]Patent: KR2016/30001,2016,A .Location in patent: Paragraph 0341; 0345-0346
[5]Patent: US2017/12214,2017,A1 .Location in patent: Paragraph 0168; 0169
[6]Patent: US10388882,2019,B2 .Location in patent: Page/Page column 73; 74

25
[ 400607-46-7 ]
C₁₄H₁₃BrS [ No CAS ]
C₃₈H₂₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene;	2-methyl-thiophene 4.1g (19.5mmol) at -78 C reacted with n-butyl lithium and triethyl borate, 5-methyl-thiophen-2-yl boronic acid to 5.03g (yield: 85%) was formed . 5-methyl-thiophen-2-yl boronic acid of 5.03g 5-bromo-2-iodo-benzoic acid methyl ester and 80 C Suzuki coupling (Suzuki coupling) Intermediate 7 by the 6.2g, (Yield: 82%) was synthesized. intermediate 7 and CH3MgCl cyclization (cyclization) to obtain intermediate 8 2.74g (yield by : 41%) was synthesized. The intermediate 8-phenyl-anthracene boronic acid compound 19 by the Suzuki coupling (4.7g, yield: 68%) was obtained. Compound 19 was confirmed by 1H-NMR and MS.

Reference： [1]Patent: KR2015/96594,2015,A .Location in patent: Paragraph 0305; 0306; 0307

26
[ 400607-46-7 ]
[ 928642-02-8 ]
C₉₉H₆₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.4 g	With tetrakis(triphenylphosphine) palladium(0); dipotassium hydrogen phosphate; In 1,4-dioxane; water; at 80℃; for 7h;	1. 3g (1. 17 millimols) of Pd (PPh 3) 4 is, 200 ml of water and 200 ml of benzodioxane 6. 2g (10. 4 millimols) of 4, 4, 8, 8, 12, 12-hexamethylindane -2, 6, 10-tribromostyrene -4H, 8H, 12H-dihydrobenzo [1, 9] [...] [3, 4, 5, 6, 7-defg] Aminoacridine (from the example 1) and 9. 9g (31. 2 millimols) of 10-(1-naphthyl)-9-dimethylanthryl arylboronic acid, 14. 9g (70. 2 millimols) of K 3 PO 4 unsatd. added to a mixture of nitrogen, 7 80 C heated in suspension. 0. 08g of NaCN is, then added, the water phase is separated. The organic phase is water, is 2 , Na 2 SO 4 the drying. The residue is obtained, the recrystallization from toluene. The precipitated crystals, the suction filtration, washed in 50 ml ethanol vacuum dried, 99 by HPLC. 6% purity of> 10. 4g (8. 1 millimols) (corresponding to 80% of a theoretical value) of the product is obtained.

Reference： [1]Patent: JP5813707,2015,B2 .Location in patent: Paragraph 0068; 0069

27
[ 7424-70-6 ]
[ 400607-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide / chloroform / 3 h / Reflux 2: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere 2.2: 2 h / -78 - 20 °C / Inert atmosphere 2.3: Inert atmosphere
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h 2.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C 2.2: 12 h / 20 °C

	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h 2.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C 2.2: 12 h / -78 - 20 °C
	Multi-step reaction with 2 steps 1.1: bromine / dichloromethane 2.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 2.2: 24 h / -78 - 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1.1: bromine / dichloromethane / 0 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 2.2: 2 h / -78 - 20 °C
	Multi-step reaction with 2 steps 1.1: bromine / dichloromethane / 0 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 2.2: 3 h / -78 - 20 °C
	Multi-step reaction with 2 steps 1.1: bromine / dichloromethane / 0 - 20 °C 2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C 2.2: 3 h / -78 - 20 °C
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / 1,2-dichloro-ethane / 2 h / 0 - 10 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 2 h / -85 - -75 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: bromine / dichloromethane / 0 - 20 °C 2: n-butyllithium / tetrahydrofuran / 3 h / -78 - 20 °C

Reference： [1]Current Patent Assignee: WS Co.,Ltd; Suk, Moon Gi; Kim, Gyu Sik; Oh, Yu Jin - KR101548370, 2015, B1
[2]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR2016/90242, 2016, A
[3]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - US2017/12214, 2017, A1
[4]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung); HODOGAYA CHEMICAL CO LTD - US10388882, 2019, B2
[5]Current Patent Assignee: SFC Ltd.; Kim Hui-dae; Lee Yu-rim - KR102017506, 2019, B1
[6]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR102030587, 2019, B1
[7]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR102030388, 2019, B1
[8]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR101554591, 2015, B1
[9]Current Patent Assignee: XI'AN MANARECO NEW MATERIALS CO LTD - CN110963876, 2020, A
[10]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR102162247, 2020, B1

28
[ 150-46-9 ]
[ 400607-04-7 ]
[ 400607-46-7 ]

Yield	Reaction Conditions	Operation in experiment
46%	With n-butyllithium; In tetrahydrofuran; hexane; at -78℃; for 0.5h;	The compound (4) 5.0 g (13.0 mmol) was melted in theanhydrous THF 200 mL and it cooled to -78. Here, the n-butyl lithium (1.6M normal hexane solution) 9.8 mL(15.7 mmol) was gradually added and the triethylborate 2.66 g (18.2 mmol) was added after doing 30 min. mixing and it stirred day and night. 2N hydrochloric acid solution 20 mL was added and the organic layer was separated for 1 hour after doing the mixing. The organic layer was diluted to the ethyl acetate 800 mL and it filtered it concentrated to water after doing washing to theMagnesium Sulfate Anhydrous the drying. The concentration residue was melted in the dichloromethane and itrecrystallized and it dried and the compound (5) 2.08 g(yield 46%) was obtained from the normal hexane withfiltering.

Reference： [1]Patent: KR101548370,2015,B1 .Location in patent: Paragraph 0104; 0105; 0106; 0111; 0112

29
[ 400607-46-7 ]
5-(3-bromophenyl)-5H-pyrido[3,2-b]indole [ No CAS ]
C₄₁H₂₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 18h;Reflux;	The compound (6) 0.50 g (1.44 mmol) and 5 - (3-bromophenyl) -5H- pyrido [3,2-b] indole (5-(3-bromophenyl)-5H-pyrido(3,2-b)indole) 0.39 g (1.20 mmol) were melted in the toluene 5 mL and ethanol 2 mL and the tetrakis triphenylphosphine palladium 0.042 g (0.036 mmol) and 2M potassium carbonate aqueous solution 2 mLwere added and it mixed reflux for 18 hours. The reaction mixture the dichloromethane 50 mL was added afterdoing the cooling in a room temperature and organic layer were washed with water and it was concentrated under reduced pressure. After the toluene 10 mL was added to the concentration residue and it was stirred for1 hour and the precipitate was created it filtered. Theprecipitate filtered was melted in the dichloromethaneand it recrystallized and it dried and the compound ( 3-2, and the mks-3-20) 0.24 g (yield 37%) were obtained from the normal hexane with filtering.

Reference： [1]Patent: KR101548370,2015,B1 .Location in patent: Paragraph 0104; 0105; 0106; 0113; 0114; 0116

30
[ 400607-46-7 ]
5-(4'-bromobiphenyl-4-yl)-5H-pyrido[3,2-b]indole [ No CAS ]
C₄₇H₃₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; for 12h;Reflux;	The compound (10) 0.50 g (1.00 mmol) and (9-phenyl-9H-carbazole -3-yl)boronic acid ((9-phenyl-9H-carbazol-3-yl) boronic acid) 0.32 g (1.10 mmol) were melted in the toluene 5 mL and ethanol 2 mL and the tetrakis triphenylphosphine palladium 0.035 g (0.030 mmol) and 2M potassium carbonate aqueous solution 1.5 mL were added and it mixed reflux for 12 hours. The reactionmixture the dichloromethane 50 mL was added after doing the cooling in a room temperature and the organic layer was washed with water and until toluene remained with about 3 mL it was stirred after doing the vacuum concentration for 1 hour. After the generated precipitate was filtered after decompression the humid body the major product was separated into the column chromatography (ethyl acetate / normal hexane 1:3 → 1:2) and the compound ( 3-13, and the mks- 4-7 ) 0.30 g(yield 45%) were obtained.

Reference： [1]Patent: KR101548370,2015,B1 .Location in patent: Paragraph 0193; 0194; 0195; 0196; 0197

31
[ 400607-46-7 ]
trifluoromethanesulfonic acid 7(10-phenylanthracene-9-yl)naphthalene-2-yl ester [ No CAS ]
9-(naphthalene-1-yl)-10-(7-(10-phenylanthracen-9-yl)naphthalen-2-yl)anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 3h;Reflux; Inert atmosphere;	Under a nitrogen environment, as a fifth intermediate compound, trifluoro-methanesulfonic acid 7-(10-phenyl-anthracene-9-yl) Naphthalen-2-yl ester 5.28 g (10-naphthalen-1-yl ) anthracene-9-yl) boronic acid (3.83 g), tetrakis (triphenylphosphine) palladium (0) (pd (pph3) 4, 0.23 g, 5.51 g of potassium phosphate, and a mixed solvent of toluene and ethanol (toluene/ethanol 40 ml = 9/1 (volume ratio ) ) was added to the flask and stirred for 5 minutes. Thereafter, 4 ml of water is added and refluxed for 3 hours. After heating, cooling the reaction solution, 40 ml of methanol is added to the precipitate filtered. Further, the pellet was washed with methanol and water, thereby obtaining the targeted by the compound represented by the formula (1-57) crude product. The crude product by silica gel short column purification (solvent: toluene ) by using methanol and ethyl acetate mixed solvent (methanol/ethyl acetate = 4/1 (volume ratio ) ) for cleaning, and re-crystallized by toluene, and then subjected to sublimation purification, thus obtained as the target compound 9-(naphthalene-1-yl ) -10-(7-(10-phenyl-anthracene-9-yl) naphthalene-2-yl ) anthracene 4 g (yield: 60%) of the flow are shown in the following reaction 8 ″

Reference： [1]Patent: CN102675032,2016,B .Location in patent: Paragraph 0263; 0264; 0280-0283

32
[ 400607-46-7 ]
[ 151391-00-3 ]
2,7-bis(10-(naphthalen-1-yl)anthracene-9-yl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; for 3h;Reflux; Inert atmosphere;	In a nitrogen atmosphere, the first intermediate compound bis (trifluoromethanesulfonic acid ) naphthalene-2, 7-di-yl ester 8.49 g, ) 14.62 g (10-naphthalen-1-yl) anthracene-9-yl boric acid, tetrakis (triphenylphosphine) palladium (0) (((Pd(PPh3)4 ) ) 0.69g, potassium phosphate 16.98g, and a mixed solvent of toluene and ethanol (toluene/ethanol 80 ml = 4/1 (volume ratio ) ) was added to the flask and stirred for 5 minutes. Then, 7 ml of water is added and refluxed for 3 hours. After heating, cooling the reaction solution, 100 ml of methanol is added to the precipitate filtered. Further, the pellet was washed with methanol and water, thereby obtaining the targeted by the compounds represented by formula (1-22) crude product. The crude product by silica gel short column purification (solvent: toluene ) by using methanol and ethyl acetate mixed solvent (methanol/ethyl acetate = 4/1 (volume ratio) ) for cleaning, and re-crystallized by toluene, and then subjected to sublimation purification, so as to obtain the target compound as the 2, 7-bis (10-(naphthalen-1-yl ) anthracene-9-yl) naphthalene, 8.9 g (yield: 61% ) the process is shown in the following reaction 3. "

Reference： [1]Patent: CN102675032,2016,B .Location in patent: Paragraph 0253-0258

33
[ 400607-46-7 ]
[ 1571902-21-0 ]
C₃₈H₂₄N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium phosphate; bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; water; for 6h;Reflux;	[Formula 2-C] (10g, 41.5mmol) and (10- (1-yl) anthracene-9-yl) boronic acid ((10- (naphthalen-1-yl) anthracen-9-yl) a boronic acid) (14.5g, 41.5mmol) is added to 150mL dioxane. In the K3PO4 25g it was dissolved in water 50mL.After In the Pd (Pt-Bu3) 2 0.3g was refluxed under stirring for 6 hours. After cooling to room temperature, the resulting solid was filtered. The filteredBy carrying out the solid was recrystallized with chloroform and ethanol to produce a [Formula 1-38] (14.2g, yield 67%).

Reference： [1]Patent: KR2015/37712,2015,A .Location in patent: Paragraph 0246-0247

34
[ 400607-46-7 ]
5-bromo-2-{4-(pyridin-3-yl)phenyl}-2H-naphtho[1,2-d][1,2,3] triazole [ No CAS ]
5-{10-(naphthalene-1-yl)anthracene-9-yl}-2-{4-(pyridin-3-yl)phenyl}-2H-naphtho[1,2-d][1,2,3]triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; for 9h;Inert atmosphere; Reflux;	4.0 g of the above-mentioned second intermediate halide {10-(naphthalen-1-yl)anthracene-9-yl} boronic acid 2M Potassium carbonate aqueous solution 15 ml Toluene 40 ml Ethanol 16 ml Tetraquistriphenylphosphine palladium (O) 0.1 g was added to a reaction vessel purged with nitrogen, and the mixture was heated under reflux for 9.0 hours with stirring. The organic layer was collected by separating operation, Concentrated and then purified by column chromatography to obtain 5-{10-(naphthalen-1-yl)anthracene-9-yl}-2-{4-(pyridin-[1,2-d] [1,2,3] triazole (Yield: 67.0%)(Compound 9).

Reference： [1]Patent: KR2015/123264,2015,A .Location in patent: Paragraph 0422-0429

35
[ 400607-46-7 ]
C₂₂H₂₂Br₂ [ No CAS ]
C₇₀H₅₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51.6%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 16h;Inert atmosphere; Reflux;	In a 250 mL three-necked flask,Compound 3 (2.23 g, 5 mmol) was added,10- (1-naphthyl) -anthracene-9-boronic acid (4.17 g, 12 mmol),K2CO3 (5.5 g, 40 mmol),Toluene (85 mL),Deionized water (24 mL),N2 protection,Pd (PPh3) 4 (320 mg) was added,Heating to reflux,The reaction was carried out for 16 hours,Stop reaction,Cooling,Liquid separation,50 mL of deionized water,The organic phase was collected,The solvent was removed,The resulting crude product was purified by silica gel column chromatography,The eluent was n-hexane: dichloromethane = 5: 1 (v / v)To obtain the target substance C06,Crude weight 2.7g,Further purification by sublimation using a chemical vapor deposition system,A sublimation temperature of 370 C,To obtain 2.3 g of the target compound C06,Yield 51.6%.

Reference： [1]Patent: CN104893713,2016,B .Location in patent: Paragraph 0063; 0064; 0065; 0066

36
[ 400607-46-7 ]
C₁₇H₁₅BrN₂O [ No CAS ]
C₄₁H₃₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 4h;Reflux;	[Compound A-7] (10g, 29.1mmol) and (10 - (naphthalen-l - yl) anthracene-9 - yl) boronic acid ((10 - (naphthalen-1-yl) anthracen-9-yl) boronic acid ) (10.6g, 30.6mmol), were charged to a 100mL THF. It was added dissolved in water K2CO313g 50 ml. After the input of the catalyst Pd (PPh3) 4 0.6g was stirred and refluxed for 4 hours. After cooling to room temperature the resulting solids were filtered. The filtered solid was recrystallized with chloroform and ethanol, filtered after, drying the [Formula 1-21] (10.6g, 64% yield) was prepared.

Reference： [1]Patent: KR2015/37711,2015,A .Location in patent: Paragraph 0339; 0340

37
[ 400607-46-7 ]
C₁₈H₁₇BrN₂ [ No CAS ]
C₄₂H₃₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 4h;Reflux;	[Compound B-6] (10g, 29.3mmol) and (10- (1-yl) anthracene-9-yl) boronic Shanshan ((10- (naphthalen-1-yl) anthracen-9-yl) boronic acid ) (10.6g, 30.6mmol), were charged to a 100mL THF. It was added dissolved in water K2CO313g 50 ml. After the input of the catalyst Pd (PPh3) 4 0.6g was stirred and refluxed for 4 hours. After cooling to room temperature the resulting solids were filtered. The filtered solid was recrystallized with chloroform and ethanol, filtered, back, and dried to prepare a [Formula 1-76] (12.3g, 74% yield).

Reference： [1]Patent: KR2015/37711,2015,A .Location in patent: Paragraph 0364; 0365

38
[ 400607-46-7 ]
C₃₇H₂₉Br [ No CAS ]
C₆₁H₄₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; at 120℃; for 3h;Inert atmosphere;	0.7 g (1 eq, 1.33 mmol) of intermediate 2, 9-naphthylanthracene-10-ylboronic acid (1.1 eq, 1.46 mmol) And 0.06 g (0.04 eq, 0.05 mmol) of tetrakis (triphenylphosphine) palladium (0) were placed in a reaction vessel, vacuum dried and then filled with nitrogen gas. 8 ml of toluene was added to dissolve the compounds Ethanol 4 ml And 4 ml (3 eq, 3.99 mmol) of a 2.0 M sodium carbonate aqueous solution were added, and the mixture was refluxed and stirred at 120 C for 3 hours. After completion of the reaction, the reaction solution was washed with distilled water and the organic layer was extracted with ethyl acetate. After drying with magnesium sulfate, the solvent was evaporated. Thereafter, the compound 9 0.42 g (Yield: 53%).

Reference： [1]Patent: KR2016/21390,2016,A .Location in patent: Paragraph 0355-0359

39
[ 400607-46-7 ]
C₃₅H₂₅Br [ No CAS ]
C₅₉H₄₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; at 120℃; for 3h;Inert atmosphere;	0.7 g (1 eq, 1.33 mmol) of intermediate 2, 9-naphthylanthracene-10-ylboronic acid (1.1 eq, 1.46 mmol) And 0.06 g (0.04 eq, 0.05 mmol) of tetrakis (triphenylphosphine) palladium (0) were placed in a reaction vessel, vacuum dried and then filled with nitrogen gas. 8 ml of toluene was added to dissolve the compounds Ethanol 4 ml And 4 ml (3 eq, 3.99 mmol) of a 2.0 M sodium carbonate aqueous solution were added, and the mixture was refluxed and stirred at 120 C for 3 hours. After completion of the reaction, the reaction solution was washed with distilled water and the organic layer was extracted with ethyl acetate. After drying with magnesium sulfate, the solvent was evaporated. Thereafter, the compound 9 0.42 g (Yield: 53%).

Reference： [1]Patent: KR2016/21390,2016,A .Location in patent: Paragraph 0350-0354

40
[ 400607-46-7 ]
C₂₃H₁₄BrN [ No CAS ]
C₄₇H₂₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 4h;Reflux;	Compound A-4 (5 g, 13.0 mmol)And 10-(naphthalen-1-yl)anthracene-9-ylboronic acid (10-(naphthalen-1-yl)anthracene-9-ylboronic acid , 5.21 g, 14.96 mmol) were dispersed in THF (100 mL) K2CO3 aqueous solution (50 mL) was added, Pd (PPh3) 4 (0.3 g, 2 mol%) was added, and the mixture was refluxed for 4 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered,And dried to give Compound 1-9 (5.9 g, yield 75%). MS: [M]+=607

Reference： [1]Patent: KR101640636,2016,B1 .Location in patent: Paragraph 0177-0180

41
[ 400607-46-7 ]
C₂₃H₁₄BrN [ No CAS ]
C₄₇H₂₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 4h;Reflux;	Compound A-6 (5 g, 13.0 mmol) and 10-(naphthalen-1-yl)anthracene-9-ylboronic acid (10-(naphthalen-1-yl)anthracene-9-ylboronic acid , 5.21 g, 14.96 mmol) were dispersed in THF (100 mL) K2CO3 aqueous solution (50 mL) was added, Pd (PPh3) 4 (0.3 g, 2 mol%) was added, and the mixture was refluxed for 4 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to obtain Compound 1-167 (5.83 g, yield 74%). MS: [M]+=607

Reference： [1]Patent: KR101640636,2016,B1 .Location in patent: Paragraph 0185-0188

42
[ 400607-46-7 ]
C₂₃H₁₄ClN [ No CAS ]
C₄₇H₂₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium phosphate; bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; water; for 20h;Reflux;	Compound A-10 (5 g, 14.7 mmol) and 10-(naphthalen-1-yl)anthracene-9-ylboronic acid (10- (naphthalen-1-yl)anthracene-9-ylboronic acid , 5.63 g, 16.2 mmol)were dispersed in dioxane 2M K3PO4 aqueous solution (30 mL) was added, Pd (PtBu3) 2 (0.15 g, 2 mol%) was added, and the mixture was refluxed for 20 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered, and dried to give Compound 1-68 (6.33 g, yield 71%). MS: [M]+=607

Reference： [1]Patent: KR101640636,2016,B1 .Location in patent: Paragraph 0189-0192

43
[ 400607-46-7 ]
C₂₇H₁₄F₉NO₃S [ No CAS ]
C₄₇H₂₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 5h;Reflux;	Compound A-16 (10 g, 16.5 mmol)and 10- (naphthalene-1-yl) anthracene-9-ylboronic acid, (10- (naphthalene-1-yl) anthracene-9-ylboronic acid, 6.35 g, 18.23 mmol) was dispersed in THF (150 mL) and 2M K2CO3 aqueous solution (75 mL) was added, Pd (PPh3) 4 (0.38 g, 2 mol%) was added, and the mixture was refluxed for 5 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from chloroform and ethanol, filtered and dried to give Compound 1-125 (7.71 g, yield 77%). MS: [M]+=607

Reference： [1]Patent: KR101640636,2016,B1 .Location in patent: Paragraph 0205-0208

44
[ 850650-61-2 ]
[ 400607-46-7 ]
C₄₀H₂₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50.9%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 12h;Reflux;	In a 1000-mL L 4-neck round-bottom flask, Intermediate 5-c (28.5 g, 0.082 mol), Pd(PPh3)4 (1.5 g, 0.001 mol), potassium carbonate (18.1 g, 0.13 mol), and Intermediate 4-b (20.3 g, 0.07 mol) were stirred together with toluene (250 mL), ethanol (125 mL) and water (125 mL) for 12 hrs under reflux. After completion of the reaction, the organic layer was separated while the aqueous layer was extracted once with toluene (200 mL). The pooled organic layer was concentrated in a vacuum, and recrystallized in toluene and methanol to afford [Compound 40] (21.1 g, 50.9%). The compound was identified through NMR. (0172) δ 8.34 (1H), 8.13-7.97 (5H), 7.80 (1H), 7.77 (1H), 7.76-7.49 (11H), 7.48-7.23 (7H)
50.9%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 12h;Reflux;	28.5 g (0.082 mol) of Intermediate 5-c, 1.5 g (0.001 mol) of Pd(PPh3)4, 18.1 g (0.13 mol) of potassium carbonate, and 20.3 g (0.07 mol) of Intermediate 1-e were added to a 1000 mL four neck round bottom flask, and then 250 mL of toluene, 125 mL of ethanol, and 125 mL of water were added thereto and refluxed for 12 hours. After refluxing for 12 hours (or after completing the reaction), an organic layer was separated therefrom and a water layer was extracted once with 200 mL of toluene. The organic layer was vacuum evaporated and then recrystallized with toluene and methanol to obtain a compound represented by Formula 67 (21.1 g, 50.9%) and NMR spectroscopy was performed to identify the same. δ 8.34 (1H), 8.13-7.97 (5H), 7.80 (1H), 7.77 (1H), 7.76-7.49 (11H), 7.48-7.23 (7H)

Reference： [1]Patent: US2017/12214,2017,A1 .Location in patent: Paragraph 0170-0172
[2]Patent: US10388882,2019,B2 .Location in patent: Page/Page column 74

45
[ 400607-46-7 ]
[ 22082-99-1 ]
9-(naphthalene-1-yl)-10-(4-(naphthalene-2-yl)phenyl)anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.92%	With potassium carbonate; In ethanol; water; at 70 - 76℃; for 2h;Inert atmosphere;	Under the protection of argon gas, In a 500mL three-necked flask with a condenser and a thermometer, Add (10-(1-naphthyl)anthracene-9-)boronic acid (10.0g), 2-(4-bromophenyl)naphthaleneanthracene (18.31g), ethanol (300ml), Pd-132 (0.020g) , Continue to increase the temperature to 70 ~ 76 , continue to add dropwise K2CO3 aqueous solution (K2CO3 aqueous solution is made by mixing 37.94g K2CO3 with 25ml of ultra-pure water) (continue to drop 2h),After the dropwise addition, the reaction was refluxed at 70-76 for 2h. The reflux liquid was cooled to 5-20, filtered, and the filter cake was washed to neutrality (pH=7), at -0.08MPa-0.09MPa, 70 Dry to constant weight at 8013.83 g of crude anthracene substituted at 9,10 position was obtained with a yield of 95.03% and a HPLC purity of 99.2028%. The obtained crude 9,10 substituted anthracene is further purified. The specific operation steps are as follows:A. Add 138ml of toluene to the crude anthracene substituted at the 9,10 position, heat to reflux for 20min, then lower the temperature to 60C, and then pass through the insulated silica gel column (silica gel 3g, column temperature is 60C),After concentration through column liquid to 1g: 4ml toluene, stop concentration, cool to 0, stir and crystallize for 2h, filter to obtain the first recrystallized solid, HPLC purity is 99.9782%;B. Add 200ml DMF to the first recrystallized solid,Heat and reflux to dissolve, the solution is cooled to 0 , stirred and crystallized for 1h, filtered to obtain the second recrystallized solid;C. Add 138ml of ethanol to the second recrystallized solid, heat and reflux to elute for 1h, cool to 0C, stir and crystallize for 1h, filter,The solid obtained is dried at -0.08MPa to -0.09MPa and 80 to 90C to obtain 9-(1-naphthyl)-10-(4-(2-naphthyl)phenyl)anthracene as a white solid 12.94 g, HPLC purity is 99.9901% (HPLC spectrum of 9-(1-naphthyl)-10-(4-(2-naphthyl)phenyl)anthracene is shown in FIG. 1), the yield is 88.92%.
82%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; for 24h;Inert atmosphere; Reflux;	2.83 g (10 mmol) of Intermediate-4 and 3.48 g (10 mmol) of Intermediate-11 were introduced under nitrogen and dissolved in 50 ml of toluene. Pd (PPh3) 4(0.5 mmol) of 2M K2CO3 and 15 ml (30 mmol) of 2M K2CO3, respectively, and refluxed for 24 hours.After completion of the reaction, the temperature of the reaction mixture was cooled to room temperature, 200 ml of MC and 200 ml of H2O were added to extract the MC layer,Dried over MgSO4, concentrated, and then subjected to column chromatography with Hex: MC = 3: 1 to obtain 4.15 g (82%) of Compound 12.

Reference： [1]Patent: CN110963876,2020,A .Location in patent: Paragraph 0044; 0058-0085
[2]Patent: KR2017/49295,2017,A .Location in patent: Paragraph 0258-0264

46
[ 400607-46-7 ]
[ 86843-98-3 ]
C₃₆H₂₃N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 12h;Reflux; Inert atmosphere;	In the reaction flask,Intermediate 2-1 (1.5 g, 5.5 mmol) was added,9- (1-naphthyl) -10-anthracene boronic acid (1.9 g, 5.5 mmol)Potassium carbonate (1.5 g, 11 mmol),Tetrahydrofuran (30 ml), water (10 ml),Tetraphenylphenylphosphine palladium (0.1 g)Heated under reflux under nitrogen for 12 hours,Cooling, removing the solvent, extracting with methylene chloride, drying and concentrating,The crude product was purified by column chromatography to give 1.5 g of product, 56%

Reference： [1]Patent: CN106749234,2017,A .Location in patent: Paragraph 0044; 0047; 0048

47
[ 400607-46-7 ]
C₂₈H₁₉Br [ No CAS ]
C₅₂H₃₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 10h;Reflux; Inert atmosphere;	In the flask,Was added 2- (4-bromophenylnaphthalene) -1,4-diphenylnaphthalene (1.4 g, 3.2 mmol)9- (1-naphthyl) -10-boronic acid (1.1 g, 3.2 mmol)Potassium carbonate (0.9 g, 6.5 mmol)Tetraphenylphenylphosphine palladium (0.2 g),Tetrahydrofuran (20 mL) and water (10 ml)Heated under reflux under nitrogen for 10 hours,Cooling, removing tetrahydrofuran, filtering,The filter cake was recrystallized from tetrahydrofuran and ethanol to give 1.6 g, 76% yield.

Reference： [1]Patent: CN106831313,2017,A .Location in patent: Paragraph 0062; 0063; 0064; 0065

48
[ 400607-46-7 ]
C₁₃H₈BrF₃O₅S [ No CAS ]
C₃₆H₂₃BrO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58.94%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 5h;Inert atmosphere; Reflux;	A mixture of 41.4 g of compound 98-a (100.0 mmol) obtained in step (1)20.7 g of potassium carbonate (150 mmol),120g water,31.3 g of phenylboronic acid (90 mmol) and 230 g of toluene,Under the protection of nitrogen,The catalyst was added to 0.9 g of Pd (PPh3) 4 (0.75 mmol)And then heated to reflux,At the same time using thin layer chromatography (TLC) to track the reaction process, about 5.0 hours after the reaction is completed,After cooling to room temperature, the system is layered and then washed with water. The organic phase is depressurized to remove the solvent to a non-distillate and then treated with petroleumEther ethyl acetate mixture The residue was subjected to column chromatography, wherein the volume ratio of petroleum ether to ethyl acetate was petroleum ether: BEthyl acetate = 5: 1 to give 30.1 g of compound 98-b in a yield of 58.94%.

Reference： [1]Patent: CN106588531,2017,A .Location in patent: Paragraph 0212; 0213; 0214

49
[ 121-43-7 ]
[ 400607-04-7 ]
[ 7732-18-5 ]
[ 400607-46-7 ]

Yield	Reaction Conditions	Operation in experiment
83%		In a 1 L reaction vessel, add 50 g (271 mmol) of and 500 mL of tetrahydrofuran, and cool to -78 C in a nitrogen atmosphere. After 30 minutes, 203 mL (325 mmol) of 1.6 M n-butyllithium was slowly added dropwise and the mixture was stirred at -78 C for 1 hour.33.8 g (325 mmol) of trimethylborate was slowly added dropwise at -78 C, and the mixture was stirred at room temperature for 2 hours, and then a 2 M aqueous hydrochloric acid solution was added thereto and stirred. Extraction with ethyl acetate and H2O and concentration of the organic layer under reduced pressure. And recrystallized with heptane to obtain 51 g. (Yield: 83%)
76%		In a round bottom flask, 9-bromo-10- (naphthalen-1-yl) anthracene (30.6 g, 80 mmol) prepared in Synthesis Example 10-1-b) was dissolved in 220 mL of THF.N-butyllithium (60 mL) was slowly added while cooling to -78 C.After the addition, the mixture was stirred at -78 C. for about 1 hour, and trimethyl borate (11.8 g, 112 mmol) was added thereto.After stirring for 1 hour at -78 , and stirred for 2 hours at room temperature2N hydrochloric acid solution was added to adjust acidity.Crystals were extracted with hexane, followed by extraction with EA, to obtain 21 g (yield 76%) of (10- (naphthalen-1-yl) anthracene-9-yl) boronic acid.
76.2%		In a round bottom flask, 9-bromo-10- (naphthalen-1-yl) anthracene (26 g, 68 mmol) prepared in Synthesis Example 1-1-b was dissolved in 210 mL of THF. N-butyllithium (51 mL) was slowly added while cooling to -78 C.After the addition, the mixture was stirred at -78 C. for about 1 hour, and trimethyl borate (33.1 g, 95 mmol) was added thereto. After stirring at -78 C. for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2N hydrochloric acid solution was added to adjust acidity. Crystals were extracted with hexane, followed by extraction with EA, and solvents were removed to obtain 18 g (yield 76.2%) of (10-naphthalen-1-yl) anthracene-9-yl) boronic acid.

76.2%		In a round-bottom flask, 9-bromo-10-(naphthalen-1-yl)anthracene (26 g, 68 mmol) prepared in Synthesis Example 5-1-b was dissolved in 210 mL of THF. N-butyllithium (51 mL) was slowly added while cooling to -78 C. After the addition, the mixture was stirred at -78 C for about 1 hour, and then trimethyl borate (33.1 g, 95 mmol) was added. After stirring at -78 C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and 2N hydrochloric acid aqueous solution was added to adjust the acidity. After extraction with EA, the solvent was removed and crystals were obtained with hexane to obtain 18 g (10-naphthalen-1-yl)anthracene-9-yl)boronic acid (yield 76.2%).
76.2%		In a round bottom flask, 9-bromo-10-(naphthalen-1-yl)anthracene (26 g, 68 mmol) prepared in Synthesis Example 1-1-b was dissolved in 210 mL of THF. After cooling to -78 C, n-butyllithium (51 mL) was slowly added. After the addition was completed, trimethyl borate (33.1 g, 95 mmol) was added after stirring at -78 C for 1 hour. After stirring at -78C for 1 hour, the mixture was stirred at room temperature for about 2 hours, and then a 2N aqueous hydrochloric acid solution was added to adjust the acidity. After extraction with EA, crystals were obtained with hexane while removing the solvent to obtain 18 g of (10-naphthalen-1-yl)anthracene-9-yl)boronic acid (yield 76.2%).

Reference： [1]Patent: KR2017/55704,2017,A .Location in patent: Paragraph 0111; 0124-0129
[2]Patent: KR102030587,2019,B1 .Location in patent: Paragraph 0425; 0432-0434
[3]Patent: KR102030388,2019,B1 .Location in patent: Paragraph 0284; 0285; 0291; 0292
[4]Patent: KR101554591,2015,B1 .Location in patent: Paragraph 0296; 0303; 0304
[5]Patent: KR102162247,2020,B1 .Location in patent: Paragraph 0307-0308

50
[ 400607-46-7 ]
C₁₉H₁₂ClNO₂ [ No CAS ]
C₄₃H₂₇NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium phosphate; bis(dibenzylideneacetone)-palladium(0); tricyclohexylphosphine; In 1,4-dioxane; water; for 7h;Reflux;	[Compound K] (10 g, 28.7 mmol) and [Compound L] (9.2 g, 28.7 mmol) were added to 150 mL of dioxane. 100 ml of 2M K3PO4, 0.5 g of Pd (dba) 2 and 0.5 g of PCy3 were added, and the mixture was refluxed for 7 hours. The mixture was cooled to room temperature, filtered, and the resulting solid was recrystallized from chloroform and ethanol to give [Compound 49] (11.2 g, yield 66%

Reference： [1]Patent: KR2017/127376,2017,A .Location in patent: Paragraph 0145-0147

51
[ 400607-46-7 ]
2,8-bis(3-bromo-9H-carbazol-9-yl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]
2,8-bis(3-(10-(naphthalen-1-yl)anthracen-9-yl)-9H-carbazol-9-yl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 24h;Reflux;	To a mixture of toluene (40 ml), ethanol (20 ml) and water (20 ml) 2,8-bis (3-bromo-9H-carbazol-9-yl) -6,12-dihydro-5,11-methanodibenzo [b, f] [1,5] diazocine (1 g, 1.41 mmol) (10- (naphthalen-1-yl) anthracen-9-yl) boronic acid (1.23 g, 3.52 mmol)tetrakis (triphenylphosphine) palladium (0) (0.081 g, 0.0705 mmol),2M potassium carbonate (20 ml) was added and refluxed for 24 hours.After the reaction solution was cooled, the solvent was removed by decompression.After extraction with dichloromethane, the organic layer was separated, dried with sodium sulfate (anhydrous), and then decompressed to remove the solvent. After recrystallization from ethanol, recrystallization with Hexane: EA = 3: 1 gave a solid product (1.03 g, 64.0%).

Reference： [1]Patent: KR101800666,2017,B1 .Location in patent: Paragraph 0263-0266

52
[ 400607-46-7 ]
[ 1042269-05-5 ]
2,8-bis-(10-naphthalen-1-yl-anthracen-9-yl)-6H,12H-5,11-methano-dibenzo[b,f][1,5]diazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 24h;Reflux;	The mixture of (5S,11S)-2,8-dibromo-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocin (2) (1.00 g, 2.63 mmol),<strong>[400607-46-7](10-(naphthalen-1-yl)anthracen-9-yl)boronic acid</strong> (3)(2.29 g, 6.58 mmol), tetrakis(triphenylphosphine)palladium(0) (0.15 g, 0.13 mmol), 2M potassium carbonate(20 ml) in toluene (40 mL), ethanol (20 mL) andwater (20 mL) was refluxed for 24 hours and cooled toroom temperature. The solvents were evaporated underreduced pressure, and the residue was extracted withdichloromethane. The organic extracts were washed withwater, dried over anhydrous sodium sulfate, and filteredoff. After evaporation of the solvent, the crudeproduct was chromatographed on silica gel with hexaneto afford a white solid product (AK-1NA) (1.28 g, 60 %).1HNMR (400 MHz, CDCl3): δ = 8.56 (s, 2H), 8.06-7.99(m, 14H), 7.68-7.66 (m, 2H), 7.52 (m, 2H), 7.53-7.38(m, 12H), 7.24-7.22 (m, 2H) 7.07 (d, 2H) 4.60 (d, 2H),4.22 (s, 2H), 4.10 (d, 2H). Anal. Calcd. for C63H42N2(%): C, 91.49; H, 5.12; N, 3.39. Found: C, 91.17; H, 5.38;N, 3.45.

Reference： [1]Journal of Nanoscience and Nanotechnology,2018,vol. 18,p. 2171 - 2174

53
[ 400607-46-7 ]
(5S,11S)-2,8-bis(4-bromonaphthalen-1-yl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]
2,8-Bis(4-(10-(naphthalen-1-yl)anthracen-9-yl)naphthalen-1-yl)-6,12-Dihydro-5,11-Methanodibenzo[b,f][1,5]Diazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.5%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 24h;Reflux;	The mixture of (5S, 11S)-2,8-bis(4-bromonaphthalen-1-yl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine(6) (1.20 g, 1.90 mmol), <strong>[400607-46-7](10-(naphthalen-1-yl)anthracen-9-yl)boronic acid</strong> (1.65 g, 4.74 mmol), tetrakis(triphenylphosphine)palladium(0) (0.11 g, 0.095 mmol)and 2 M potassium carbonate (20 ml) in toluene (40 mL),ethanol (20 mL) and water (20 mL) was refluxed for24 hours and cooled to room temperature. The solventswere evaporated under reduced pressure, and the residuewas extracted with dichloromethane. The organic extractswere washed with water, dried over anhydrous sodiumsulfate, and filtered off. After evaporation of the solvent,the crude product was extracted with hot hexane. Evaporationof the solvent gave a yellow solid product (0.86 g,52.5%). 1H NMR (400 MHz, CDCl3): δ= 854 (s, 2H),8.09-8.04 (m, 10H), 7.94 (s, 2H), 7.68 (d, 6H), 7.60-7.55(m, 12H), 7.49-7.45 (m, 10H), 7.34-7.31 (d, 6H), 4.60(d, 2H), 4.22 (s, 2H), 4.10 (d, 2H). Anal. Calcd. forC83H54N2 (%): C, 92.36; H, 5.04; N, 2.60. Found C,91.94; H, 5.42; N, 2.64.

Reference： [1]Journal of Nanoscience and Nanotechnology,2018,vol. 18,p. 2162 - 2165

54
[ 400607-46-7 ]
C₁₈H₁₀ClN [ No CAS ]
C₄₂H₂₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; In tetrahydrofuran; for 4h;Reflux;	Compound H (6 g, 22 mmol),(10- (naphthalen-1-yl) anthracen-9-yl) boronic acid (8g, 23mmol)BTP (0.02 g, 0.04 mmol) and 2 M K 2 CO 3 (20 mL) were added to 100 mL of THF and stirred under reflux for 4 hours.After completion of the reaction,The catalyst was removed and extracted with toluene (20 mL * 3 times). The organic layer was dried over MgSO4 and distilled under reduced pressure. and purified by short silica column chromatography (EtOAc: Hexane) to obtain Compound M (8.5 g, 71%).

Reference： [1]Patent: KR2018/28010,2018,A .Location in patent: Paragraph 0305-0309

55
[ 400607-46-7 ]
(5S,11S)-2,8-bis(10-bromoanthracen-9-yl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]
(5S,11S)-2,8-bis(10'-(naphthalen-1-yl)-[9,9'-bianthracen]-10-yl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51.2%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 18h;Reflux;	Toluene (40 mL) And ethanol (15 ml), Water (15 ml) Was added to the mixed solution (5S, 11S) -2,8-bis (10-bromoanthracen-9-yl) -6,12-dihydro-5,11-methanodibenzo [b, f] [1,5] diazocine (1.5 g, 2.05 mmol), (10- (naphthalen-1-yl) anthracen-9-yl) boronic acid (1.6 g, 4.6 mmol) tetrakis (triphenylphosphine) palladium (0) (0.12 g, 0.1 mmol), And potassium carbonate (1 g, 7.2 mmol) And the mixture was heated under reflux for 18 hours. After cooling the reaction solution, The solvent was removed by decompression. After extraction with dichloromathane, the organic layer was separated and dried with sodium sulfate (anhydrous) The solvent was removed by decompression. Hexane was used as a developing solvent to prepare a liquid Chromatographic separation and purification gave white To obtain a solid compound KKY11 (1.23 g, 51.2%).

Reference： [1]Patent: KR101843569,2018,B1 .Location in patent: Paragraph 0270-0273

56
[ 400607-46-7 ]
(5S,11S)-2,8-bis(4-bromonaphthalen-1-yl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]
(5S,11S)-2,8-bis(4-(10-(naphthalen-1-yl)anthracen-9-yl)naphthalen-1-yl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.5%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 24h;Reflux;	Toluene (40 mL) And ethanol (20 ml), Water (20 ml) Was added to the mixed solution Dihydro-5,11-methanodibenzo [b, f] [1,5] diazocine (1.20 g, 1.90 mmol) was added to a solution of (5S, 11S) -2,8-bis (4-bromonaphthalen- , (10- (naphthalen-1-yl) anthracen-9-yl) boronic acid (1.65 g, 4.74 mmol) tetrakis (triphenylphosphine) palladium (0) (0.11 g, 0.095 mmol), And 2M potassium carbonate (20 ml) And the mixture was refluxed for 24 hours. After cooling the reaction solution, The solvent was removed by decompression. After extraction with dichloromathane, the organic layer was separated and dried with sodium sulfate (anhydrous) The solvent was removed by decompression. And extracted with hot hexane to obtain compound KKY16 (0.86 g, 52.5%).

Reference： [1]Patent: KR101843569,2018,B1 .Location in patent: Paragraph 0188; 0194-0196

57
[ 400607-46-7 ]
(8S,16S)-5,13-dibromo-7,15-dihydro-8,16-methanodinaphtho[1,2-b:1',2'-f][1,5]diazocine [ No CAS ]
(8S,16S)-5,13-bis(10-(naphthalen-1-yl)anthracen-9-yl)-7,15-dihydro-8,16-methanodinaphtho[1,2-b:1',2'-f][1,5]diazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.1%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 18h;Reflux;	Toluene (60 mL) And ethanol (20 ml), Water (20 ml) Was added to the mixed solution (8S, 16S) -5,13-dibromo -7,15-dihydro-8,16-methanodinaphtho [1,2-b: 1 ', 2'-f] [1,5] diazocine (2.00 g, 4.16 mmol), (10- (naphthalen-1-yl) anthracen-9-yl) boronic acid (3.48 g, 9.99 mmol) tetrakis (triphenylphosphine) palladium (0) (0.24 g, 0.21 mmol), And potassium carbonate (2.30 g, 16.64 mmol) And the mixture was heated under reflux for 18 hours. After cooling the reaction solution, The solvent was removed by decompression. After extraction with dichloromathane, the organic layer was separated and dried with sodium sulfate (anhydrous) The solvent was removed by decompression. Hexane was used as a developing solvent to be separated and purified by liquid chromatography to obtain a yellow solid compound KKY19 (2.28 g, 59.1%).

Reference： [1]Patent: KR101843569,2018,B1 .Location in patent: Paragraph 0253; 0259-0261

58
[ 400607-46-7 ]
[ 390357-42-3 ]
2,8-bis(10-(naphthalen-1-yl)anthracen-9-yl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 24h;Reflux;	Toluene (40 mL) And ethanol (20 ml), Water (20 ml) Was added to the mixed solution 2,8-dibromo-6,12-dihydro-5, 11-methanodibenzo [b, f] [1,5] diazocine (1 g, 2.63 mmol), (10- (naphthalen-1-yl) anthracen-9-yl) boronic acid (2.29 g, 6.58 mmol) tetrakis (triphenylphosphine) palladium (0) (0.15 g, 0.13 mmol), And 2M potassium carbonate (20 ml) were added and the mixture was refluxed for 24 hours. After cooling the reaction solution, The solvent was removed by decompression. After extraction with dichloromathane, the organic layer was separated and dried with sodium sulfate (anhydrous) The solvent was removed by decompression. Hexane as a developing solvent was separated by liquid chromatography to obtain a white solid compound KKY4 (1.28 g, 60%).

Reference： [1]Patent: KR101843569,2018,B1 .Location in patent: Paragraph 0217-0220

59
[ 400607-46-7 ]
(8S,16S)-5,13-dibromo-7,15-dihydro-8,16-methanodinaphtho[1,2-b:1',2'-f][1,5]diazocine [ No CAS ]
5,13-bis(10-(naphthalen-1-yl)anthracen-9-yl)-7,15-dihydro-8,16-methanodinaphtho[1,2-b:1',2'-f][1,5]diazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.1%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 18h;Reflux;	The mixture of (8S,16S)-5,13-dibromo-7,15-dihydro-8,16-methanodinaphtho[1,2-b:1,2-f][1,5]dia zocine (2.00 g, 4.16 mmol), <strong>[400607-46-7](10-(naphthalen-1-yl)anthracen-9-yl)boronic acid</strong>(3.48 g, 9.99mmol), tetrakis(triphenylphosphine)palladium(0)(0.24 g, 0.21mmol) and potassiumcarbonate (2.30 g, 16.64 mmol) in toluene (60 mL), ethanol (20 mL) and water (20 mL)was refluxed for 18 hours and cooled to room temperature. The solvents were evaporatedunder reduced pressure, and the residue was extracted with dichloromethane. The organicextracts were washed with water, dried over anhydrous sodium sulfate, and filtered off. Afterevaporation of the solvent, the crude product was chromatographed on silica gel with hexaneto afford a yellow solid product (2.28 g, 59.1%). 1H NMR (400 MHz, CDCl3):δ 8.45 8.41(m, 4H), 8.09 8.05 (m, 4H),7.96 7.94 (m, 6H), 7.88 7.85 (m, 6H), 7.59 7.55 (m, 6H), 7.49 7.45(m,8H), 7.42 7.40 (m, 6H) 4.61 (d, 2H), 4.25 (s, 2H), 4.09 (s, 2H).; Anal.Calcd. for C71H46N2(%): C, 91.98; H, 5.00; N, 3.02. Found: C, 91.72; H, 5.11;N, 3.17.

Reference： [1]Molecular Crystals and Liquid Crystals,2017,vol. 659,p. 94 - 99

60
[ 400607-46-7 ]
(5S,11S)-2,8-bis(10-bromoanthracen-9-yl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]
2,8-bis(10'-(naphthalen-1-yl)-[9,9'-bianthracen]-10-yl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51.2%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 18h;Reflux;	The mixture of (5S,11S)-2,8-bis(10-bromoanthracen-9-yl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine (1.5 g, 2.05 mmol), (10-(naphthalen-1- yl)anthracen-9-yl)boronic acid (1.6 g, 4.6 mmol), tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.1 mmol) and potassium carbonate (1 g, 7.2 mmol) in toluene (40 mL), ethanol (15 mL) and water (15 mL)was refluxed for 18 hours and cooled to room temperature. The solvents were evaporated under reduced pressure, and the residue was extracted with dichloromethane. The organic extracts were washed with water, dried over anhydrous sodium sulfate, and filtered off. After evaporation of the solvent, the crude product was chromatographed on silica gel with hexane to give a white solid product (1.23 g, 51.2%). 1H NMR(400MHz, CDCl3):δ 8.51 8.48 (m, 2H),8.06 8.02 (m, 6H), 7.96 7.92 (m, 12H), 7.68 7.62 (m, 8H), 7.55 7.52 (m, 2H), 7.45 7.40 (m, 8H),7.37 7.34 (m, 8H), 7.31 7.28 (m, 6H), 4.65 (d, 2H), 4.25 (s, 2H), 4.04 (s, 2H).; Anal. Calcd. for C91H58N2 (%): C, 92.67; H, 4.96; N, 2.37. Found: C,92.34; H, 5.18; N, 2.48.

Reference： [1]Molecular Crystals and Liquid Crystals,2017,vol. 659,p. 140 - 146

61
[ 400607-46-7 ]
[ 58556-75-5 ]
9-(7-bromonaphthalen-2-yl)-10-(1-naphthyl)anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Inert atmosphere; Reflux;	9AA10BA (25 g, 72 mmol, 1 eq), <strong>[58556-75-5]2,7-dibromonaphthalene</strong> (20.5 g, 1 eq.), potassium carbonate (30 g, 3 eq.), and tetrakis (triphenylphosphine) palladium(0) (2.5 g, 0.03 eq.) were weighed and put into a 1000 mL three-necked round bottom flask, and degassing under reduced pressure/Ar purge was performed. Degassing under reduced pressure and nitrogen purge were performed sufficiently. Thereafter, toluene (160 mL), ethanol (40 mL), and water (40 mL) were added thereto in a nitrogen atmosphere, and the mixture was refluxed and stirred. After completion of the reaction, heating was stopped, and the temperature of the reaction liquid was returned to room temperature. Extraction was performed with toluene, the organic solvent layers were then unified, anhydrous sodium sulfate was added thereto, and the mixture was allowed to stand for a while. Sodium sulfate was filtered off, and the solution was concentrated under reduced pressure. The resulting mixture containing a desired product was caused to pass through a silica gel short column chromatography, and a fraction containing a desired product was collected and concentrated under reduced pressure. The mixture containing a desired product was caused to pass through a silica gel column chromatography, and a fraction containing a desired product was collected and concentrated under reduced pressure. Thus, a desired product ?AB7Br? was obtained.

Reference： [1]Patent: US2018/94000,2018,A1 .Location in patent: Paragraph 0565

62
[ 400607-46-7 ]
[ 58556-75-5 ]
C₅₈H₃₈ [ No CAS ]

Reference： [1]Patent: US2018/94000,2018,A1

63
[ 400607-46-7 ]
2,8-bis(4-(1-(4-bromonaphthalen-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl)phenyl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]
2,8-bis(4-(1-(4-(10-(naphthalen-1-yl)anthracen-9-yl)naphthalen-1-yl)-1H-phenanthro[9,10-d]imidazole-2-yl)phenyl)-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; for 24h;Reflux;	To a mixed solution of dioxane (80 ml) and water (10 ml)2,8-bis (4-(1-(4-bromonaphthalen-1-yl)-1H-phenanthro[9,10-d]imidazol-2-yl)phenyl) -6,12-dihydro-methanodibenzo[b,f][1,5]diazocine (1.00 g, 0.82 mmol),<strong>[400607-46-7](10-(naphthalen-1-yl)anthracen-9-yl)boronic acid</strong> (0.72 g, 2.05 mmol), tetrakis (triphenylphosphine) palladium (0)(0.05 g, 0.041 mmol),potassium carbonate (0.45 g, 3.28 mmol)l) and refluxed for 24 hours.After the reaction solution was cooled, the solvent was removed by decompression.By DichloromathaneAfter extraction, the organic layer was separated and dried with sodium sulfate (anhydrous), and then the solvent was removed by decompression.The solid product (0.68 g, 50%) was obtained by liquid chromatography using hexane: MC = 5: 1 as a developing solvent.

Reference： [1]Patent: KR101841500,2018,B1 .Location in patent: Paragraph 0221-0224

64
[ 400607-46-7 ]
[ 131222-99-6 ]
6,12-bis[10-(1-naphthyl)-9-anthracene]chrysene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 90℃; for 12h;Inert atmosphere;	Under nitrogen protection, 9-(1-naphthalene)anthracene-10-boronic acid(13mmol4.5g), <strong>[131222-99-6]6,12-dibromochrysene</strong>(5.4mmol2. 1g), Tetrakis(triphenylphosphine)palladium(0.3mmol0.4g), Toluene (200 mL), ethanol (100 mL) and aqueous potassium carbonate solution (100 mL, 2 M) were added to a 500 mL three-necked round-bottom flask then stirred, and the mixture was heated to 90C under a nitrogen gas flow and reacted for 12 hours. After the reaction was completed, the mixture was naturally cooled to room temperature, suspended solids were precipitated, and the precipitates were filtered off, washed with water, ethanol, and acetone, respectively, then placed in a vacuum drying oven, and carried out sublimationusing a high-vacuum sublimation apparatus to obtain pale pink powder (4.0 g), yield : 89%.

Reference： [1]Patent: CN108069816,2018,A .Location in patent: Paragraph 0050-0055

65
[ 597554-03-5 ]
[ 400607-46-7 ]
[ 27973-29-1 ]
1,6-bis[10-(2-naphthyl)-9-anthracene]pyrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 90℃; for 12h;Inert atmosphere;	Under nitrogen protection, 9-(1-naphthalene)anthracene-10-boronic acid((13 mmol, 4.5 g), 6,12-Dibromochrysene(5.4mmol, 2. 1g) and 1,6-dibromopyrene(5.4mmol, 1. 9g), tetrakistriphenylphosphine palladium (0.3 mmol, 0.4g), toluene (200mL),Ethanol (100 ml) and potassium carbonate (100 ml, 2 M) were poured into a 500 ml three-necked round bottom flask, and the mixture was heated to 90C under nitrogen gas flow for 12 hours. After the reaction, the mixture was naturally cooled to room temperature, suspended solids precipitated, and the precipitates were filtered off, washed with water, ethanol, and acetone, respectively, placed in a vacuum drying oven, and sublimed using a high-vacuum sublimation apparatus to obtain pale yellow powder (3.7 g). Yield 85%.

Reference： [1]Patent: CN108069816,2018,A .Location in patent: Paragraph 0064-0067

66
[ 400607-46-7 ]
C₂₃H₁₃F₃O₄S [ No CAS ]
C₄₆H₂₈O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 80℃;	10 g (22.6 mmol) of the compound 2-1, 41.3 g (1.13 mmol) of Pd (PPh3), K2CO3,9.4 g (67.8 mmol) of (10- (naphthalen-1-yl) anthracen-9-yl) boronic acid 0.2 g (29.38 mmol)Was dissolved in DME / H2O Followed by stirring at 80 C.When the reaction is complete, EA.The organic layer was dried over MgSO4, the solvent was removed using a rotary evaporator,The target compound 2 (6 g, 47%) was obtained by column chromatography.

Reference： [1]Patent: KR2018/72058,2018,A .Location in patent: Paragraph 0095; 0096; 0099-0100

67
[ 400607-46-7 ]
[ 1054314-90-7 ]
C₃₉H₂₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 80℃;	10 g (22.6 mmol) of the compound 41-1, 41.3 g (1.13 mmol) of Pd (PPh3)4, K2CO3, 9.4 g (67.8 mmol),(10- (naphthalen-1-yl) anthracen-9-yl) boronic acid was dissolved in 0.2 g (29.38 mmol)Dissolved in DME / H2O Followed by stirring at 80 C.When the reaction was complete, it was extracted with H2O and EA.The organic layer was dried over MgSO4, the solvent was removed using a rotary evaporator,The target compound 41 (5 g, 50%) was obtained by column chromatography.

Reference： [1]Patent: KR2018/72058,2018,A .Location in patent: Paragraph 0113; 0114; 0117; 0118

68
[ 400607-46-7 ]
C₂₀H₁₂BrN₃O [ No CAS ]
C₄₄H₂₇N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 8h;Reflux; Inert atmosphere;	Intermediate C (3.9 g, 0.01 mol) and (10-(1-naphthyl)decyl-9-yl)boronic acid (4.18 g, 0.012 mmol) were added to 100 mL of toluene under nitrogen, and then charged with a catalyst. An aqueous solution of tetrakistriphenylphosphine palladium (0.12 g, 0.1 mmol) and potassium carbonate (4.14 g, 0.03 mol).The system was heated to reflux for 8 hours, and the mixture was naturally cooled to room temperature, then separated and then evaporated to give a crude product.The crude product was subjected to silica gel column chromatography, and the eluent was purified by V-hexane:V-chloroform=1:4 to obtain a yellow powder. The obtained powder was further purified by a chemical vapor deposition system at a sublimation temperature of 370 C to obtain a compound C02. The yield was 50%.

Reference： [1]Patent: CN108250213,2018,A .Location in patent: Paragraph 0024

69
[ 400607-46-7 ]
C₁₉H₁₇Br₂F₃O₃S [ No CAS ]
C₉₀H₆₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33.27%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 70℃; for 24h;Inert atmosphere;	In a 500 ml three-neck bottle,Add 100 ml of toluene, 100 ml of ethanol,50 ml of water, 2.71 g (0.005 mol) of the compound of the formula M-08,6.26 g (0.018 mol) of 9-(1-naphthyl)-indole-10-boronic acid, 5.52 g (0.04 mol) of potassium carbonate,0.12 g (0.0001 mol) of tetrakistriphenylphosphine palladium was added under nitrogen protection.Slowly heat up to 70 C for 24 hours, cool down, filter,After the filter cake is washed with water, the obtained solid silica gel column chromatography is separated, dichloromethane:The petroleum ether =1:5 eluted to obtain 1.9 g of the product represented by the formula P-17.The yield was 33.27%.

Reference： [1]Patent: CN108456130,2018,A .Location in patent: Paragraph 0108; 0114; 0115

70
[ 400607-46-7 ]
[ 1210470-49-7 ]
C₄₆H₂₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In 1,2-dimethoxyethane; for 7h;Reflux; Inert atmosphere;	8-Bromo-11 phenylbenzo [a] carbazole (2.50 g), 9- (1-naphthyl) -10-anthraceneboronic acid (2.57 g), palladium acetate (150 mg), S-Phos 550 mg) and tripotassium phosphate (4.28 g) were charged, and after purging with nitrogen, 1,2-dimethoxyethane (45 mL) and pure water (10 mL) were added and the atmosphere was purged with nitrogen. After heating under reflux for 7 hours, it was cooled and methylene chloride was added, then transferred to a separatory funnel and washed with pure water. Methylene chloride was removed from the methylene chloride solution, and the resulting residue was purified by silica gel chromatography to obtain the desired compound 1. (3.08 g: yield 77.0%)

Reference： [1]Patent: JP2015/189722,2015,A .Location in patent: Paragraph 0140; 0144

71
[ 400607-46-7 ]
[ 1210469-11-6 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
30%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; toluene for 12h; Reflux; Inert atmosphere;	2.2.5 (2-5) Synthesis of Compound 2 Under an atmosphere of nitrogen, 10-bromo-7-phenylbenzo [c] carbazole (7.45 g), 9- (1-naphthyl) -10-anthraceneboronic acid (8.36 g), tetrakis (triphenylphosphine) palladium 0) (2.31 g), sodium carbonate (4.24 g), toluene (50 mL), 1,2-dimethoxyethane (100 mL) and water (20 mL) was refluxed for 12 hours. The reaction solution was cooled to room temperature, extracted with toluene, the toluene layer was washed with saturated brine, dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain the objective compound 2 (3.58 g: 30% yield).

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - JP2015/189722, 2015, A Location in patent: Paragraph 0145; 0150

72
[ 400607-46-7 ]
[ 1607-57-4 ]
9-(naphthalen-1-yl)-10-(1,2,2-triphenylvinyl)anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 80℃; for 30h;Inert atmosphere;	Weighing 1.0 g of 9-(1-naphthyl)-10-boronic acid, triphenylbromoethylene 1.25g, potassium carbonate 1.59g, 50 mL of ethylene glycol dimethyl ether and 5 mL of water were placed in a 100 mL two-necked flask.Stir the air in the device and protect it with nitrogen. Then, 99.6 mg of tetrakis(triphenylphosphine)palladium was added under a nitrogen stream. Heat to 80 C,The reaction was refluxed for 30 hours. As the reaction proceeds,The solution changed from the original light yellow to orange-brown. The crude product solution was extracted with dichloromethane and water.The organic layer was dried over anhydrous magnesium sulfate and filtered. The crude product obtained by vacuum distillation of the filtrate was separated on a silica gel column using a mixed solvent of dichloromethane and petroleum ether in a volume ratio of 1:8.The obtained pure product solution was distilled under reduced pressure and dried in vacuo to give 0.96 g of a yellow solid compound (I-1).The purity was 99.9% and the yield was 60%.

Reference： [1]Patent: CN108530258,2018,A .Location in patent: Paragraph 0048; 0071-0073
[2]Journal of Materials Chemistry C,2020,vol. 8,p. 16858 - 16869

73
[ 400607-46-7 ]
[ 29091-56-3 ]
C₄₄H₂₉N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 90℃;Inert atmosphere;	Potassium carbonate (2.76 g, 0.02 mmol) was dissolved in toluene:In a mixed solution of ethanol:water volume ratio of 3:3:1 (50 mL),4-(4-Bromophenyl)-3,5-diphenyl-4H-1,2,4-triazole (1.13 g, 3 mmol) was added under N2 protection.10- (1-naphthyl) - anthracene-9-boronic acid (1.25g, 3.6mmol),Tetrakistriphenylphosphine palladium (0.35 g, 0.3 mmol),Heating to 90 C reflux reaction,TLC was monitored until the reaction was complete.The reaction solution was extracted with dichloromethane.The organic layer was washed with water and brine and dried.Chromatography by dichloromethane/methanol = 30/1 column.1.01 g of a gray solid product I1 was obtained. Yield: 56%.

Reference： [1]Patent: CN108658877,2018,A .Location in patent: Paragraph 0028-0030

74
[ 400607-46-7 ]
[ 589-87-7 ]
[ 1160506-32-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 80℃; for 12h;	1-Bromo-4-iodobenzene 3.11 g (11 mmol) of3.48 g (10 mmol) of Compound A,0.58 g (0.5 mmol) of tetrakispalladium,2.07 g (15 mmol) of potassium carbonate,Was placed in a round flask, and 150 mL of a toluene mixed solution in water at a ratio of 80% of the total solution volume was added to dissolve the solution Followed by stirring at 80 C for 12 hours.After cooling to room temperature, the solution was passed through a celite pad, extracted with ethyl acetate in a separating funnel, and then the solvent was removed using a rotary evaporator. 2.91 g (yield: 63%) of Compound B was obtained by column chromatography.

Reference： [1]Patent: KR2018/114470,2018,A .Location in patent: Paragraph 0218-0222

75
[ 400607-46-7 ]
C₁₉H₉BrN₂S [ No CAS ]
C₄₃H₂₄N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 70℃; for 4h;Inert atmosphere;	In 1000ml reaction flask was added 24.3g (69.4mmol) of [10- (1-naphthyl) -9-anthryl] boronic acid,Add 400 ml of tetrahydrofuran and stir to dissolve.Add 26 g (69.4 mmol) of intermediate 18,23.8 g (172.5 mmol) of potassium carbonate dissolved in 80 ml of water was added.Nitrogen was replaced for 15 minutes, and 0.79 g (0.694 mmol) of tetrakistriphenylphosphine palladium was added.Under nitrogen protection, the temperature was raised to 70 C and the reaction was carried out for 4 hours.After the reaction was completed, 100 ml of water was added, and the mixture was stirred. The organic phase was washed with 250 ml of saturated sodium chloride solution, and the organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated under reduced pressure to crystals of o-dichlorobenzene.The compound 98 was obtained in an amount of 27.1 g, and the yield was 65%.

Reference： [1]Patent: CN109776468,2019,A .Location in patent: Paragraph 0132; 0139-0143

76
[ 849222-40-8 ]
[ 400607-46-7 ]
C₅₃H₄₀O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃;Inert atmosphere;	7 g (20.10 mmol, 1 eq) of Intermediate 1a,Intermediate 2a 10.38 g (22.11 mmol, 1.1 eq),8.3 g (60.06 mmol, 3 eq) of K2CO3,0.93 g (0.80 mmol, 0.04 eq) of Pd (PPh3) 4 (tetrakis triphenylphosphine palladium)Was charged into a 500 mL 2-necked round bottom flask and charged with nitrogen.200 mL of THF (tetrahydrofuran) and 45 mL of H 2 O were added, and the mixture was heated to 80 C with stirring and reacted overnight. Columnship with DCM / Hx (dichloromethane / hexane) followed by recrystallization from EA (ethyl acetate) and precipitation in MeOH gave the pure intermediate A.

Reference： [1]Patent: KR2019/56731,2019,A .Location in patent: Paragraph 0174-0179

77
[ 400607-46-7 ]
7-bromo-2-(pyridin-2-yl)quinoline [ No CAS ]
C₃₈H₂₄N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56.1%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; for 3h;Inert atmosphere; Reflux;	Into a 1 L three-necked flask was charged 12 g (42.08 mmol) of intermediate D and 17.58 g (50.5 mmol) of 9- (1-naphthyl) -10-anthraceneboronic acid. 11.63 g (84.16 mmol) of potassium carbonate and 1.46 g (1.26 mmol) of Pd (PPh3) 4 were added thereto, followed by nitrogen substitution in 200 ml of toluene, 100 ml of H 2 O and 100 ml of ethanol, followed by stirring under reflux for 3 hours. After the reaction was completed, the mixture was extracted with MC, the organic layer was dried over MgSO 4, purified by column chromatography, and crystallized with Hex to obtain compound 16 (12 g, 56.1%).

Reference： [1]Patent: KR2019/53579,2019,A .Location in patent: Paragraph 0094; 0099-0104

78
[ 400607-46-7 ]
C₁₆H₉Br₂FN₂ [ No CAS ]
C₆₄H₃₉FN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 90℃; for 12h;Inert atmosphere;	(1) Under the protection of nitrogen,6,6'-(5-fluoro-1,3-benzene)bis(3-bromopyridine) (208 mg, 0.512 mmol),[10-(1-naphthalene)9-indole]boronic acid (428 mg, 1.23 mmol),Tetrakis(triphenylphosphine)palladium (29.6 mg, 0.026 mmol),Toluene (80 mL) and aqueous potassium carbonate (40 mL, 2M),The mixture was stirred in a 250 ml three-neck round bottom flask, and the mixture was heated to 90 C for 12 hours under the protection of a nitrogen gas stream.After the completion of the reaction, the mixture was cooled to room temperature. The crude product was washed with methylene chloride (40 ml) and water (4/30 mL).The crude product was purified by silica gel column chromatography using dichloromethane and n-hexane as a 1:2 solvent.It is then recrystallized from n-hexane with dichloromethane.372 mg of bright white crystals were obtained, yield: 85%.

Reference： [1]Patent: CN108070004,2019,B .Location in patent: Paragraph 0118-0120; 0122-0124

79
[ 400607-46-7 ]
C₁₆H₁₀Br₂N₂ [ No CAS ]
C₆₄H₄₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; at 90℃; for 12h;Inert atmosphere;	Under the protection of nitrogen,1,3-bis[2-(5-bromopyridine)]-benzene (200 mg, 0.512 mmol),[10-(1-naphthalene)9-indole]boronic acid (428 mg, 1.23 mmol),Tetrakis(triphenylphosphine)palladium (29.6 mg, 0.026 mmol),Toluene (80 mL) and aqueous potassium carbonate (40 mL, 2M),The mixture was stirred in a 250 ml three-neck round bottom flask, and the mixture was heated to 90 C for 12 hours under the protection of a nitrogen gas stream.After completion of the reaction, it was naturally cooled to room temperature, and the crude product was washed with dichloromethane (40 ml) and deionized water (4/30 mL).The organic layer was separated, dried over magnesium sulfate, filtered and evaporated to dryness.The crude product was purified by silica gel column chromatography using dichloromethane and n-hexane as a 1:2 solvent.It is then recrystallized from n-hexane with dichloromethane.A white powder of 343 mg was obtained.Yield: 80%.

Reference： [1]Patent: CN108070004,2019,B .Location in patent: Paragraph 0018-0110; 0112-0114

80
[ 400607-46-7 ]
C₁₇H₁₃Br [ No CAS ]
C₄₁H₂₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 3h;Inert atmosphere; Reflux;	In a 500 ml round-bottom flask in a nitrogen atmosphere, Compound A (6.0 g, 20.27 mmol) and a-1 (7.76 g, 22.30 mmol) were completely dissolved in 240 mL of tetrahydrofuran, followed by adding 2M aqueous potassium carbonate solution (120 mL). Tetrakis- (triphenylphosphine) palladium (0.70 g, 0.61 mmol) was added thereto, followed by heating and stirring for 3 hours. After the temperature was lowered to room temperature and filtered to remove the base, THF was completely concentrated under reduced pressure and recrystallized with 220 ml of ethyl acetate to prepare Compound 1 (5.95 g, yield: 56%).

Reference： [1]Patent: KR2019/94038,2019,A .Location in patent: Paragraph 0197-0200

81
[ 400607-46-7 ]
9-(4-bromophenyl)benzoquinoline [ No CAS ]
C₄₃H₂₇N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.9%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; toluene;Reflux;	2L round bottom flask8 g (24 mmol) of 9- (4-bromophenyl) benzoquinoline, 10 g (29 mmol) of 9- (1-naphthalene) anthracene boronic acid, 1.4 g of tetrakis (triphenylphosphine) palladium (0) (1 mmol), potassium carbonate 9.9 g (72 mmol), 40 mL of 1,4-dioxane, 40 mL of toluene, and 16 mL of water were added to reflux with stirring.After completion of the reaction, the reaction solution was cooled to room temperature, extracted with ethyl acetate and water, and the organic layers were collected and concentrated.Recrystallized from methylene chloride and methanol, filtered and dried. (8 g, 59.9%).

Reference： [1]Patent: KR102017506,2019,B1 .Location in patent: Paragraph 0252; 0268-0270

82
[ 400607-46-7 ]
C₂₁H₁₂Cl₃N₃ [ No CAS ]
C₉₃H₅₇N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; tricyclohexylphosphine; In ethanol; toluene; for 12h;Reflux; Inert atmosphere;	Weigh out compound 1-1 (5.1 g, 12.32 mmol), compound 3-1 (15.1 g, 43.1 mmol), tris (dibenzylideneacetone) dipalladium 0.50 g (0.54 mmol), and tricyclohexylphosphine 0.30 g, respectively. (1.08 mmol), 6.8 mL of a 2M potassium carbonate aqueous solution, 100 mL of toluene, and 25 mL of ethanol were added to a 500 mL three-necked flask, and heated to reflux under nitrogen protection and stirred for 12 hours. The reaction was stopped to cool to room temperature, and extracted with dichloromethane. The organic phase was retained, dried over anhydrous magnesium sulfate, and the solvent was spin-dried. The crude product was separated by silica gel column chromatography, and the eluent was a mixed solution of dichloromethane and n-hexane to obtain 8.68 g of pure product ETM-3 with a yield of 58%.

Reference： [1]Patent: CN110423214,2019,A .Location in patent: Paragraph 0081; 0082; 0083; 0084

83
[ 400607-46-7 ]
3-iodonaphthalen-2-yl trifluoromethanesulfonate [ No CAS ]
3-(10-(naphthalen-1-yl)anthracene-9-yl)naphthalen-2-yl trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene;Reflux;	22 g (55 mmol) of 3-iodonaphthalen-2-yl trifluoromethanesulfonate prepared in Synthesis Example 10-2) in a round bottom flask;1.27 g (1 mmol) of (10- (naphthalen-1-yl) anthracene-9-yl) boronic acid 20.9 g (60 mmol) tetrakis (triphenylphosphine) palladium (0) prepared in Synthesis Example 10-1) ), 15.2 g (109 mmol) of potassium carbonate, 110 mL of tetrahydrofuran, 110 mL of toluene, 44 mL of water and refluxed.When the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate / water, the organic layer was concentrated and separated by column to obtain a product. (27 g, yield 86%)

Reference： [1]Patent: KR102030587,2019,B1 .Location in patent: Paragraph 0425; 0444-0447

84
[ 870134-77-3 ]
[ 400607-46-7 ]
8-(10-(naphthalen-1-yl)anthracene-9-yl)naphthalen-2-yl trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene;Reflux;	22 g (55 mmol) of 8-iodonaphthalen-2-yl trifluoromethanesulfonate prepared in Synthesis Example 1-2) in a round bottom flask,21.9 g (60 mmol) of (10- (naphthalen-1-yl) anthracene-9-yl) boronic acid prepared in Synthesis Example 1-1)Tetrakis (triphenylphosphine) palladium (0) 1.27 g, (1 mmol) potassium carbonate 15.2 g (109 mmol) 110 mL of tetrahydrofuran, 110 mL of toluene, 44 mL of water were added under reflux.When the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate / water, the organic layer was concentrated and separated by column to obtain a product. (24 g, 80% yield)

Reference： [1]Patent: KR102030388,2019,B1 .Location in patent: Paragraph 0284; 0303-0306

85
[ 400607-46-7 ]
2,2'-(4-bromonaphthalene-1,8-diyl)bis(1,3,4-oxadiazole) [ No CAS ]
C₃₈H₂₂N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene;Reflux;	General procedure: 22 g (55 mmol) of 8-iodonaphthalen-2-yl trifluoromethanesulfonate prepared in Synthesis Example 1-2) in a round bottom flask,21.9 g (60 mmol) of (10- (naphthalen-1-yl) anthracene-9-yl) boronic acid prepared in Synthesis Example 1-1)Tetrakis (triphenylphosphine) palladium (0) 1.27 g, (1 mmol) potassium carbonate 15.2 g (109 mmol) 110 mL of tetrahydrofuran, 110 mL of toluene, 44 mL of water were added under reflux.When the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate / water, the organic layer was concentrated and separated by column to obtain a product. (24 g, 80% yield)

Reference： [1]Patent: KR102030388,2019,B1 .Location in patent: Paragraph 0284; 0303-0306; 0383; 0392-0395

86
[ 400607-46-7 ]
5-(4-bromonaphthalen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole [ No CAS ]
C₅₃H₃₄N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene;Reflux;	General procedure: 22 g (55 mmol) of 8-iodonaphthalen-2-yl trifluoromethanesulfonate prepared in Synthesis Example 1-2) in a round bottom flask,21.9 g (60 mmol) of (10- (naphthalen-1-yl) anthracene-9-yl) boronic acid prepared in Synthesis Example 1-1)Tetrakis (triphenylphosphine) palladium (0) 1.27 g, (1 mmol) potassium carbonate 15.2 g (109 mmol) 110 mL of tetrahydrofuran, 110 mL of toluene, 44 mL of water were added under reflux.When the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate / water, the organic layer was concentrated and separated by column to obtain a product. (24 g, 80% yield)

Reference： [1]Patent: KR102030388,2019,B1 .Location in patent: Paragraph 0284; 0303-0306; 0356; 0379-0382

87
[ 400607-46-7 ]
2-phenyl-7-(4-pyridinyl)naphthalen-1-yl trifluoromethanesulfonate [ No CAS ]
C₄₅H₂₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; toluene;Reflux;	General procedure: 22 g (55 mmol) of 8-iodonaphthalen-2-yl trifluoromethanesulfonate prepared in Synthesis Example 1-2) in a round bottom flask,21.9 g (60 mmol) of (10- (naphthalen-1-yl) anthracene-9-yl) boronic acid prepared in Synthesis Example 1-1)Tetrakis (triphenylphosphine) palladium (0) 1.27 g, (1 mmol) potassium carbonate 15.2 g (109 mmol) 110 mL of tetrahydrofuran, 110 mL of toluene, 44 mL of water were added under reflux.When the reaction was completed, the reaction solution was cooled to room temperature, extracted with ethyl acetate / water, the organic layer was concentrated and separated by column to obtain a product. (24 g, 80% yield)

Reference： [1]Patent: KR102030388,2019,B1 .Location in patent: Paragraph 0284; 0303-0306; 0396; 0411-0414

88
[ 400607-46-7 ]
C₃₀H₃₀Br₃N₃ [ No CAS ]
C₁₀₂H₇₅N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene;Reflux; Inert atmosphere;	Weigh 7.6 g (11.3 mmol) of intermediate a (bromo mesitylenetriazine), 13.83 g (39.6 mmol) of intermediate c (anthraceneboronic acid), 0.48 g (0.41 mmol) of tetrakis(triphenylphosphine)palladium catalyst), 6.0 mL of a 2 M potassium carbonate aqueous solution, 100 mL of toluene, and 25 mL of ethanol were added to a 500 mL three-necked flask, and heated to reflux overnight under nitrogen protection and stirred. After the reaction was stopped and cooled to room temperature, it was extracted with dichloromethane, and the organic phase was retained, dried over anhydrous magnesium sulfate, and the solvent was spin-dried. The crude product was separated by silica gel column chromatography using dichloromethane/n-hexane as the eluent. 6.83 g of compound 4 was obtained in a pure yield of 45%. C102H75N3, Exact Mass: 1342.71, Found: 1343.83; Elemental Analysis: C, 91.30; H, 5.54; N, 3.16.

Reference： [1]Patent: CN110423235,2019,A .Location in patent: Paragraph 0049-0052

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	400607-46-7	MDL No. :	MFCD11977302
Formula :	C₂₄H₁₇BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ASQXKNXJNDLXQV-UHFFFAOYSA-N
M.W :	348.20	Pubchem ID :	23088558
Synonyms :

Num. heavy atoms :	27
Num. arom. heavy atoms :	24
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	114.22
TPSA :	40.46 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.02 cm/s

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	6.2
Log Po/w (WLOGP) :	4.49
Log Po/w (MLOGP) :	4.17
Log Po/w (SILICOS-IT) :	3.97
Consensus Log Po/w :	3.77

[ CAS No. 400607-46-7 ] {[proInfo.proName]}

Quality Control of [ 400607-46-7 ]

Related Doc. of [ 400607-46-7 ]

Product Details of [ 400607-46-7 ]

Calculated chemistry of [ 400607-46-7 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 400607-46-7 ]

Application In Synthesis of [ 400607-46-7 ]

[ 400607-46-7 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 400607-46-7 ]

Organoboron

Precautionary Statements-General

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Storage

Disposal

Physical hazards

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Inquiry

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

Log S (ESOL) :	-6.43
Solubility :	0.000129 mg/ml ; 0.000000371 mol/l
Class :	Poorly soluble
Log S (Ali) :	-6.83
Solubility :	0.000051 mg/ml ; 0.000000146 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-8.79
Solubility :	0.000000561 mg/ml ; 0.0000000016 mol/l
Class :	Poorly soluble

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.58

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

Precautionary Statements-General
Code	Phrase
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P103	Read label before use
Prevention
Code	Phrase
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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.
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P285	In case of inadequate ventilation wear respiratory protection.
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Code	Phrase
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P321
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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.
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P406	Store in corrosive resistant/ container with a resistant inner liner.
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P413
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P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
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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