1097884-37-1|4-Bromo-9-phenyl-9H-carbazole| Ambeed

Structure of 1097884-37-1

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 1097884-37-1 ] Purity: 99% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 1097884-37-1 ]

CAS No. :	1097884-37-1
Formula :	C₁₈H₁₂BrN
M.W :	322.20
SMILES Code :	BrC1=CC=CC(N2C3=CC=CC=C3)=C1C4=C2C=CC=C4
MDL No. :	MFCD29067336
InChI Key :	OLLJKISFWSJGID-UHFFFAOYSA-N
Pubchem ID :	21197304

Safety of [ 1097884-37-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362

Application In Synthesis of [ 1097884-37-1 ]

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

Downstream synthetic route of [ 1097884-37-1 ]

[ 1097884-37-1 ] Synthesis Path-Downstream 1~35

1
[ 244205-40-1 ]
[ 1097884-37-1 ]

References: [1]Organic electronics,2013,vol. 14,p. 67 - 73.
[2]Patent: KR2017/90390,2017,A .
[3]Patent: KR101763838,2017,B1 .
[4]Patent: WO2017/196081,2017,A1 .
[5]Dyes and Pigments,2018,vol. 156,p. 369 - 378.
[6]Patent: KR101550429,2015,B1 .

2
[ 577-19-5 ]
[ 1097884-37-1 ]

References: [1]Organic electronics,2013,vol. 14,p. 67 - 73.
[2]Patent: KR101550429,2015,B1 .

3
[ 17613-47-7 ]
[ 1097884-37-1 ]

References: [1]Organic electronics,2013,vol. 14,p. 67 - 73.
[2]Patent: KR2016/20159,2016,A .
[3]Patent: KR2016/41223,2016,A .
[4]Patent: KR2017/90390,2017,A .
[5]Patent: KR101763838,2017,B1 .
[6]Patent: WO2017/196081,2017,A1 .
[7]Dyes and Pigments,2018,vol. 156,p. 369 - 378.
[8]Patent: KR101550429,2015,B1 .

4
[ 108-86-1 ]
[ 3652-89-9 ]
[ 1097884-37-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 110℃;	Add 31.4g of bromobenzene and 54.1g of 4-bromo-9H-carbazole to a dry 2L three-necked flask. Dry and degassed 600 mL of toluene was added as a solvent. Add 57.7g of sodium tert-butoxide, 0.9g catalyst palladium acetate (2% mol) and 5.0g ligand 1,1'- Binaphthyl-2,2'-bisdiphenylphosphine (BINAP, 4% mol). The temperature was raised to 110C and the reaction ended overnight. Cool to room temperature Add activated carbon adsorption, suction filtration, remove solvent, Recrystallization from toluene and ethanol gave 52.8 g of Intermediate Q (yield 82%).
79%	With 18-crown-6 ether; copper; potassium carbonate; In water; for 10h;Reflux;	4-Bromo-9H-carbazole (6 g, 24.38 mmol), copper powder (3.09 g, 48.76 mmol) and 18-crown-6 (0.65 g, 2.44 mmol) were dissolved in bromobenzene (60 ml) followed by addition of K2CO3 (8.29 g, 2 M) in water (30 ml). The mixture was refluxed for 10 h and cooled to room temperature and extracted with methylene chloride and water. The combined organic layer was dried over MgSO4 and concentrated. Purification by column chromatography using n-hexane gave a white form. The product was obtained to 6.2 g(yield 79%). 1H NMR (200 MHz, CDCl3): δ 8.84 (d, 1H, J = 8.0 Hz), 7.66-7.19(m, 11H). MS (FAB) m/z 323[(M + H)+].
77%	With dibenzo-18-crown-6; potassium acetate; copper; In N,N-dimethyl-formamide; at 120℃; for 4h;	Intermediate 2-1 (2.1 g, 0.010 mol) in bromobenzene (1.6 g, 0.010 mol), dibenzo-18-crown-6 (1.1 g, 0.0030 mol), copper (2) (1.2 g, 0.020 mol), potassium acetate Insertthe DMF to 100 mL (2.8 g, 0.020 mol) was reacted with stirring for 4 hours at 120 C.After layer separation the MC column purification (n-Hexane:: MC) After completion ofthe reaction by cooling to H20 to afford 2.3 g of Intermediate 2-2 (yield 77%)

77%

With dibenzo-18-crown-6; potassium acetate; copper; In N,N-dimethyl-formamide; at 120℃; for 4h;

General procedure: 2-aminobenzamide (1.4g, 0.010mol) in dibromochloromethane (2.1g, 0.010mol) dibenzo-18-crown-6 (1.1g, 0.0030mol), copper (2) (1.2g, 0.020mol), potassium acetate (2.8 g, 0.020mol), into a DMF in 100ml was reacted with stirring for 4 hours at 120 C. After the reaction cooled to H20: After layer separation the MC column purification (n-Hexane: MC) to yield the intermediate 1-1 1.1g (62% yield). Intermediate 1-8 (2.1g, 0.010mol) put in bromobenzene (1.6g, 0.010mol), by synthesis by the same method used in preparation Example 1-1 to give <Intermediate 1-9> 2.3g (yield 77%).

References: [1]Patent: CN107686484,2018,A .Location in patent: Paragraph 0171-0176.
[2]Organic electronics,2013,vol. 14,p. 67 - 73.
[3]Patent: KR2016/20159,2016,A .Location in patent: Paragraph 0356; 0360-0362.
[4]Patent: KR2016/41223,2016,A .Location in patent: Paragraph 0100; 0103; 0133-0135.

5
[ 1097884-37-1 ]
C₄₂H₂₉N₂OP [ No CAS ]

References: [1]Organic electronics,2013,vol. 14,p. 67 - 73.

6
[ 1097884-37-1 ]
[ 644-97-3 ]
C₄₂H₂₉N₂P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		4-Bromo-9-phenyl-9H-carbazole (3.5 g, 10.86 mmol) was dissolved in tetrahydrofuran (35 ml) under argon atmosphere at -78 C followed by addition of n-butyllithium (5 ml, 2.5 M). After 1 h, dichlorophenylphosphine (0.81 ml, 5.98 mmol) was added slowly. The mixture was stirred for 2 h at -78 C, and allowed to warm to room temperature. After overnight stirring, the reaction mixture was added to methanol (10 ml) for 2 h and extracted with water and methylene chloride. The combined organic layer was dried over MgSO4 and concentrated. Purification by column chromatography using methylene chloride : n-hexane (1:4) gave a white powder. After vacuum drying for 2 h, the white powder was dissolved in methylene chloride (10 ml) and hydrogen peroxide (2 ml) was added followed by stirring for 2 h. The combined organic layer was dried over MgSO4 and concentrated. The product was obtained to 1.3 g (yield 20%).

References: [1]Organic electronics,2013,vol. 14,p. 67 - 73.

7
[ 1097884-37-1 ]
6-(9-phenyl-9H-carbazol-4-yl)-9H-pyrido[2,3-b]indole [ No CAS ]

References: [1]Dyes and Pigments,2016,vol. 130,p. 183 - 190.

8
[ 1097884-37-1 ]
(9-phenyl-9H-carbazol-4-yl)boronic acid [ No CAS ]

References: [1]Dyes and Pigments,2016,vol. 130,p. 183 - 190.

9
[ 150-46-9 ]
[ 1097884-37-1 ]
C₂₂H₂₂BNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[1097884-37-1]4-bromo-9-phenyl-9H-carbazole</strong> (0.50 g, 0.16 mmol) was vacuumdried for 3 h, dissolved in THF under a nitrogen atmosphere,and stirred for 30 min at -30 C. n-buthyl lithium (0.12 g,0.19 mmol) was slowly injected into the solution, which was subsequently stirred for 1 h. Triethylborate (0.27 g, 0.19 mmol) was added into the reaction mixture, and the solution was stirred for afurther 12 h at room temperature. 2 M aqueous hydrochloric acid was poured into the solution, which was then stirred for 30 min. The solution was neutralized with potassium carbonate and extracted using methylene chloride and distilled water. The organic layer was dehydrated with magnesium sulfate and reprecipitatedusing n-hexane. The mixture was filtered, and the precipitate was obtained as a white solid. Yield 90% (0.40 g), 1H NMR (400 MHz, DMSO-d6): d 8.55 (s, 2H),8.50 (d, 1H, J8.0 HZ), 7.70 (t, 2H, J7.8 HZ), 7.57 (t, 3H, 7.0 HZ), 7.38(d, 2H, J8.4 HZ), 7.34-7.31 (m, 2H), 7.26-7.22 (m, 2H) MS (ESI) m/z211.2 [(M + H)].

References: [1]Dyes and Pigments,2016,vol. 130,p. 183 - 190.

10
[ 3652-89-9 ]
[ 591-50-4 ]
[ 1097884-37-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With copper(l) iodide; potassium carbonate; 1-(2-pyridyl)-3-(2-pyridyl)-1,3-propanedione; In N,N-dimethyl-formamide; at 110℃;Inert atmosphere;	A 500 ml four-neck flask is initially charged with 15.0 g (61.0 mmol, 1.0 eq) of 4-bromo-9H-carbazole 1a (CAS 3652-89-9) together with 13.6 ml (122 mmol, 2.0 eq) of iodobenzene 2a and 16.8 g (122 mmol, 2.0 eq) of potassium carbonate, which are dissolved in 180 ml of dried DMF. After degassing by means of a nitrogen stream for 30 minutes, 1.38 g (6.10 mmol, 0.10 eq) of 1,3-di(2-pyridyl)-1,3-propanedione and 1.16 g (6.10 mmol, 0.10 eq) of copper(I) iodide are added. The mixture is stirred at 110 C. overnight and, after the reaction has ended, the solvent is removed on a rotary evaporator. The residue is taken up in 250 ml of DCM, conc. ammonium chloride solution is added and the mixture is filtered through Celite. Subsequently, the phases are separated, the aqueous phase is extracted twice with 100 ml each time of DCM and the combined organic phases are finally washed with water. After drying over sodium sulphate and removing the solvent under reduced pressure, the oily residue together with heptane is filtered through silica gel and the solvent is again removed on a rotary evaporator. 19.0 g(59.0 mmol, 97%) of a colourless oil 3a are obtained.
95%	With dibenzo-18-crown-6; copper; potassium carbonate; at 150℃; for 24h;	Intermediate 1-2 (1 g, 0.0041 mol) iodo benzene (2.1 g, 0.0102 mol / sigma Aldrich) potassium carbonate (2.2 g, 0.0163 mol), dibenzo-18-crown-6 (0.1 g, 0.0004 mol / sigma Aldrich) , 30 ml of bromobenzene was added to Copper (0.5 g, 0.0081 mol / sigma aldrich) and stirred at 150 C. for 24 hours for reaction. After the completion of the reaction, the mixture was cooled and separated by H20: MC, followed by column purification (n-Hexane: MC) to obtain 1.3g of intermediate 1-3 (yield 95%).
92%	With 18-crown-6 ether; copper; potassium carbonate; In 1,2-dichloro-benzene; at 140℃; for 16h;Sealed tube;	4-bromo-9H-carbazole (4-bromo-9H-carbazole) 50g (203.16mmol), iodo- benzene (Iodobenzene) 68mL (609.48mmol), Cu1.3g (20.32mmol), K2CO3 56g (406.32mmol) , 18-crown-6-ether (18-crown-6-ether) 6.6g (20.32mmol) 1,2-dichlorobenzene (1,2-dichlorobenzene) 140C with 1L, in a sealed tube (sealed tube) It was reacted for 16 hours. After the reaction was complete, after cooling to room temperature and extracted with distilled water and dichloromethane (dichloromethane). The organic layer was dried over anhydrous MgSO4After removing the solvent on a rotary evaporator then it was purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain the title compound A-1 60.0g (92%).

89%	With 1,10-Phenanthroline; 18-crown-6 ether; potassium carbonate; copper(l) chloride; In 1-methyl-pyrrolidin-2-one; at 180℃;Inert atmosphere;	Under nitrogen protection, 4-bromocarbazole (20g, 81.3mmol),Iodobenzene (99.5g, 487.6mmol),Cuprous chloride (4.0g, 40.6mmol),Potassium carbonate (168.5g, 1218.9mmol), 18-crown-6 (10.7g, 40.6mmol),1,10-Phenanthroline (7.3g, 40.6mmol) and N-methylpyrrolidone (508mL) were added to a three-necked flask and reacted at 180 C overnight. After cooling to room temperature, distilled water was added, the mixture was extracted with dichloromethane, the organic phase was washed with water, the organic phase was dried over anhydrous sodium sulfate and concentrated to remove the solvent, and the residue was purified by column chromatography (pure petroleum ether) to give beige oily intermediate B 116g (yield: 89%).
88%	With 18-crown-6 ether; copper; potassium carbonate; In 1,2-dichloro-benzene; at 180℃; for 24h;	4-bromo-9H-carbazole 20.0 g (81.3 mmol), 2-iodobenzene 33.2 g (162.5 mmol), copper powder 10.3 g (162.5 mmol), 18-crown-6 4.3 g (16.3 mmol), 33.7 g (243.9 mmol) of potassium carbonate was added in order, 200 ml of 1,2-dichlorobenzene was added, and the mixture was refluxed and stirred at 180 C. for 1 day. When the reaction was completed, the solution was concentrated under reduced pressure after a high temperature filter, and the organic layer solution was subjected to column chromatography with hexane to obtain 21.0 g of [Intermediate 1-e]. (Yield 88%)
88%	With 18-crown-6 ether; copper; potassium carbonate; In 1,2-dichloro-benzene; at 180℃; for 24h;	4-bromo-9H-carbazole 20.0 g (81.3 mmol), 2-iodobenzene 33.2 g (162.5 mmol),Copper powder 10.3 g (162.5 mmol), 18-crown-6 4.3 g (16.3 mmol), potassium carbonate 33.7 g (243.9 mmol) were added in order,After adding 200 ml of 1,2-dichlorobenzene, the mixture was refluxed and stirred at 180 C. for 1 day.When the reaction was completed, the solution was concentrated under reduced pressure after high-temperature filtering, and the organic layer solution was subjected to column chromatography with hexane to obtain 21.0 g of [Intermediate 5-b]. (Yield 88%)
83%	With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux;	A 5 L flask was charged with 200.0 g (0.8 mol) of intermediate 4-bromo-9H-carbazole,248.7 g (1.2 mol) of iodobenzene,168.5 g (1.2 mol) of potassium carbonate,31.0 g (0.2 mol) of copper iodide (CuI) 29.3 g (0.2 mol) of 1,10-phenanthroline was added to 2.5 L of N, N-dimethylformamide,And refluxed under a nitrogen stream for 24 hours.The resulting mixture was added to 4 L of distilled water, and the crystallized solid was filtered, washed with water, methanol and hexane. The obtained solid was extracted with water and dichloromethane, and the obtained water was removed from the obtained organic layer using magnesium sulfate. The filtrate was concentrated and purified by column chromatography to obtain Intermediate C-1 as a white solid (216.2 g, 83% yield) .
83%	With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; for 24h;Reflux; Inert atmosphere;	In a 5 L flask, Bromo-9H-carbazole 200.0 g (0.8 mol),248.7 g (1.2 mol) of iodobenzene,168.5 g (1.2 mol) of potassium carbonate,31.0 g (0.2 mol) of copper (I) iodide,29.3 g (0.2 mol) of 1,10-phenanthrolineAfter adding 2.5 L of N, N-dimethylformamide,And refluxed under a nitrogen stream for 24 hours.The resulting mixture was added to 4 L of distilled water, and the crystallized solid was filtered, washed with water, methanol and hexane.The obtained solid was extracted with water and dichloromethane, and water was removed from the obtained organic layer using magnesium sulfate and concentrated,Purification by column chromatography gave Intermediate C-1 as a white solid(216.2 g, 83% yield).
83%	With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux;	A 5 L flask was charged with 200.0 g (0.8 mol) of intermediate 4-bromo-9H-carbazole, 248.7 g (1.2 mol) of iodobenzene, 168.5 g (1.2 mol) of potassium carbonate, 31.0 g (0.2 mol) of copper (I) iodide and 29.3 g (0.2 mol) of 1,10-phenanthroline were added to 2.5 L of N, N-dimethylformamide, And refluxed under a nitrogen stream for 24 hours. The resulting mixture was added to 4 L of distilled water and the crystallized solid was filtered, Water and methanol,Washed with hexane. The obtained solid was extracted with water and dichloromethane, and the obtained aqueous layer was extracted with magnesium sulfate. The filtrate was concentrated and purified by column chromatography to obtain Intermediate I-1 as a white solid (216.2 g, 83% yield) .
83%	With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; for 24h;Inert atmosphere; Reflux;	A 5 L flask was charged with 200.0 g (0.8 mol) of intermediate 4-bromo-9H-carbazole,248.7 g (1.2 mol) of iodobenzene,168.5 g (1.2 mol) of potassium carbonate,31.0 g (0.2 mol) of copper (I) iodide,29.3 g (0.2 mol) of 1,10-phenanthroline,Was added to 2.5 L of N, N-dimethylformamide,And refluxed under a nitrogen stream for 24 hours.The resulting mixture was added to 4 L of distilled water, and the crystallized solid was filtered, washed with water, methanol and hexane. The obtained solid was extracted with water and dichloromethane, and the obtained aqueous layer was extracted with magnesium sulfate. The filtrate was concentrated and purified by column chromatography to obtain Intermediate I-1 as a white solid (216.2 g, 83% yield) .
83%	With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; for 24h;Reflux; Inert atmosphere;	200.0 g (0.8 mol) of an intermediate of 4-bromo-9H-carbazole, 248.7 g (1.2 mol) of iodo benzene, 168.5 g (1.2 mol) of potassium carbonate, 31.0 g (0.2 mol) of copper(I) iodide, and 29.3 g (0.2 mol) of 1,10-phenanthroline were mixed with 2.5 L of N,N-dimethylformamide in a 5 L flask, and the mixture was refluxed under a nitrogen flow for 24 hours. The obtained mixture was added to 4 L of distilled water, and a solid crystallized therein was filtered and washed with water, methanol, and hexane. Subsequently, the solid was extracted with water and dichloromethane, and an organic layer obtained therefrom was treated by using magnesium sulfate to remove moisture and then, concentrated and purified through column chromatography to obtain Intermediate I-1 as a white solid (216.2 g, a yield of 83%).
81%	With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 24h;Inert atmosphere;	[287] In a 100 ml round-bottom three-neck flask under a nitrogen atmosphere, 2.6 g of Intermediate 24, 2.6 g of iodobenzene, 0.2 g of copper iodide, 0.2 g of1, 10-phenanthroline, 4.4 g of potassium carbonate and 30 ml of dimethylfomiamide were placed, and reacted at 80C for 24 hrs. The reaction solution was cooled and then extracted with dichloromethane and water. The extracted solution was concentrated, subjected to column chromatography using a solvent mixture of dichloromethane and n-hexane and then concentrated, thus obtaining 2.7 g of Intermediate 25 (yield 8 1%).[288] MS (ESI): [M+Hj 322
75%	With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In toluene; at 100℃;	Reaction is progressed in 100C after putting the sub 6-4-4 (4.9g, 20mmol), sub 6-4-5 (4.1g, 20mmol), pd2(dba)3 (0.9g, 1 mmol), PPh3 (0.5g, 2mmol), NaOt-Bu (5.8g, 60mmol), toluene (210mL) in the round bottom flask. If reaction was completed the organic compound which was dry to the MgSO4 and was the organic layer generated after doing the concentration was re-determined as ether and water after doing the extraction with the silicagel column and the Sub 6-4-6 was obtained with 4.8g (yield : 75%).
75%	With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In toluene; at 100℃;	To a round bottom flask Sub 1-1-4-1 (4.9g, 20mmol), Sub 1-1-5-1 (4.1g, 20mmol), Pd2 (dba) 3 (0.9g, 1mmol), PPh3 (0.5g , 2mmol), and NaOt-Bu (5.8g, 60mmol), the reaction proceeds at 100 C after loading into toluene (210mL). After the reaction was completed, the organic layer was dried over MgSO4 and the ether was extracted with water and the resulting organics concentrated to silica gel column and recrystallized the Sub 1-1-6-1 4.8g (yield: 75%) was obtained.
73%	With 18-crown-6 ether; copper; potassium carbonate; In N,N-dimethyl-formamide; at 190℃; for 12h;Inert atmosphere;	A 1000 mL 2-neck round bottom flask was charged with intermediate 6-2 (100.0 mmol, 24.6 g), Iodobenzene (120.0 mmol, 24.5 g),Cu-metal (110.0 mmol, 7.0 g), K2CO3 (150.0 mmol, 20.7 g),18-Crown-6 (10.0 mmol, 2.64 g) was charged and charged with nitrogen. 500 mL of dimethylformamide was added as a solvent, and the mixture was refluxed at 190 DEG C for 12 hours.The temperature of the reaction solution was lowered to room temperature and extracted with water and diethyl ether. The obtained extract was dried over MgSO4 and dried under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel column chromatography to obtain 23.5 g (yield: 73%) of Intermediate 6-3 as a yellow solid.
68%		4-bromo-9Hcarbazole(2 g, 8 mmol), copper(Ι) iodide (1.24 g, 6.5 mmol), cesiumcarbonate (7.98 g, 24 mmol) were added to 25 mL of anhydrous toluenesolution in 3-neck round bottom flask under N2 atmosphere. After themixture was heated at 80 C, iodobenzene (1.82 mL, 16 mmol), ethylenediamine(0.82 mL, 12.2 mmol) was added to mixture. Then themixture was refluxed at 110 C for 15 h (1.7 g, Yield 68%) 1H NMR(300 MHz, THF): δ(ppm) 8.81-8.78 (d, 1H), 7.65-7.59 (t, 2H),7.56-7.47 (m, 3H), 7.45-7.40 (m, 2H), 7.35-7.27 (q, 3H), 7.25-7.20 (t,1H).
	With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In toluene; at 100℃; for 24h;	2-bromo-9H-carbazole ( 327mmol) and iodobenzene (360mmol), toluene (2800mL) Pd2(dba) 3 (8.24g, 9mmol), PPh3 (7.87g, 30mmol), NaOt-Bu ( 86.5g, 900mmol) were added to each, and refluxed under stirring for 24 hours at 100 C. ether and extracted with water and the organic layer is MgSO 4 and then dried, and concentrated to the resulting organic silicagel column and recrystallization to give the 2-bromo-9-phenyl- 9H-carbazole.
	With 18-crown-6 ether; copper; potassium carbonate; In N,N-dimethyl-formamide; at 190℃; for 12h;Inert atmosphere;	A 1000 mL 2-neck round bottom flask was charged with intermediate 6-2 (100.0 mmol, 24.6 g), Iodobenzene (120.0 mmol, 24.5 g), Cu metal (110.0 mmol, 7.0 g), K2CO3 (150.0 mmol, 20.7 g), 18-Crown-6 (10.0 mmol, 2.64 g) was charged and charged with nitrogen. To this was added 500 mL of dimethylformamide as a solvent And then refluxed at 190 C for 12 hours. The temperature of the reaction solution was lowered to room temperature and extracted with water and diethyl ether. The obtained extract was dried over MgSO4 and dried under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel column chromatography to obtain 23.5 g (yield: 73%) of Intermediate 6-3 as a yellow solid

References: [1]Patent: US10957859,2021,B2 .Location in patent: Page/Page column 201.
[2]Patent: KR101550429,2015,B1 .Location in patent: Paragraph 0107; 0116-0119.
[3]Patent: KR101579289,2015,B1 .Location in patent: Paragraph 0376-0379.
[4]Patent: CN111100129,2020,A .Location in patent: Paragraph 0110; 0111-0113.
[5]Patent: KR102081617,2020,B1 .Location in patent: Paragraph 0354; 0375-0379.
[6]Patent: KR102149450,2020,B1 .Location in patent: Paragraph 0476; 0482-0486.
[7]Patent: KR2017/48094,2017,A .Location in patent: Paragraph 0150-0152.
[8]Patent: KR2017/129468,2017,A .Location in patent: Paragraph 0418-0422.
[9]Patent: KR2019/32884,2019,A .Location in patent: Paragraph 0364-0369.
[10]Patent: KR2019/36867,2019,A .Location in patent: Paragraph 0417-0421.
[11]Patent: US2019/198780,2019,A1 .Location in patent: Paragraph 0170-0172.
[12]Patent: WO2017/196081,2017,A1 .Location in patent: Paragraph 285; 286; 287; 288.
[13]Patent: KR2016/10878,2016,A .Location in patent: Paragraph 0227; 0232; 0233.
[14]Patent: KR2015/69256,2015,A .Location in patent: Paragraph 0112-0113; 0118-0119.
[15]Patent: KR101763838,2017,B1 .Location in patent: Paragraph 0107; 0118-0121.
[16]Dyes and Pigments,2018,vol. 156,p. 369 - 378.
[17]Patent: KR2015/43669,2015,A .Location in patent: Paragraph 0153; 0156; 0161; 0162.
[18]Patent: KR2017/90390,2017,A .Location in patent: Paragraph 0125; 0138-0141.

11
[ 5419-55-6 ]
[ 1097884-37-1 ]
(9-phenyl-9H-carbazol-4-yl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		Sub 6-4-6 (6.4g, 20mmol) were melted in the anhydrous Ether. The temperature of the reactant was lowered to -78 C. After n-BuLi (2.5M in hexane) (1.4g, 22mmol) were dipped as the slowly the reactant was mixed for 30 minutes. Thereafter, the temperature of the reactant was again lowered to -78 C and Triisopropyl borates (5.6g, 30mmol) were dipped. At a room temperature, after agitating water is put in and it attenuates and 2N HCl is put. If reaction was completed the organic compound which was dry to the MgSO4 and was the organic layer generated after doing the concentration was re-determined as the ethyl acetate and water after doing the extraction with the silicagel column and the Sub 6-4 was obtained with 4.1g (yield : 71%).
71%		1-1-6-1 Sub (6.4g, 20mmol) was dissolved in anhydrous Ether, lowering the temperature of the reaction to -78 C, n-BuLi (2.5M inhexane) was added dropwise (1.4g, 22mmol) slowly, and after , the reaction is stirred for 30 min. After lowering the temperature of the reaction back to the -78 C triisopropyl borate (5.6g, 30mmol) was added dropwise. After stirring at room temperature and diluted with water 2N HCl was added, After completion of reaction, the organic layer was dried over MgSO4, concentrated and extracted with ethyl acetate and water silica gel column and recrystallized the Sub 1-1-7-1 4.1g (yield: 71%) was obtained and then produced.
70%		Intermediate 2-2 (3.9g, 0.012mol) and then dissolved in 30ml anhydrous THF, was added dropwise at -78? Slowly to n-BuLi (2.5M) 5.9ml. After holding for 1 hour, followed by the addition of triisopropyl borate (3.4g, 0.018mol), was stirred at room temperature for 24 hours. After stirring for 1 hour into a 1N HCl After the reaction, EA: After layer separation the H2O was recrystallized with n-Hexane to give the 2.0g (70% yield).

References: [1]Patent: KR2016/10878,2016,A .Location in patent: Paragraph 0226; 0227; 0234; 0235.
[2]Patent: KR2015/69256,2015,A .Location in patent: Paragraph 0112-0113; 0120-0121.
[3]Patent: KR2016/40826,2016,A .Location in patent: Paragraph 0367-0369.

12
[ 98-80-6 ]
[ 1097884-37-1 ]

References: [1]Patent: KR2016/10878,2016,A .
[2]Patent: KR2015/43669,2015,A .
[3]Patent: KR2015/69256,2015,A .

13
[ 32337-96-5 ]
[ 1097884-37-1 ]

References: [1]Patent: KR2016/10878,2016,A .
[2]Patent: KR2015/43669,2015,A .
[3]Patent: KR2015/69256,2015,A .

14
2'-bromo-6'-nitro-1,2-dihydro-1,1'-biphenyl [ No CAS ]
[ 1097884-37-1 ]

References: [1]Patent: KR2016/10878,2016,A .
[2]Patent: KR2015/43669,2015,A .
[3]Patent: KR2015/69256,2015,A .

15
[ 1097884-37-1 ]
C₄₄H₂₆N₄S [ No CAS ]

References: [1]Patent: KR2016/10878,2016,A .

16
[ 1097884-37-1 ]
C₃₀H₁₈N₂O₂S [ No CAS ]

References: [1]Patent: KR2016/10878,2016,A .

17
[ 1097884-37-1 ]
C₃₀H₁₈N₂S [ No CAS ]

References: [1]Patent: KR2016/10878,2016,A .

18
[ 5419-55-6 ]
[ 1097884-37-1 ]
[ 7732-18-5 ]
(9-phenyl-9H-carbazol-4-yl)boronic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		Sub 1-1-1 (6.4g,20mmol) was dissolved in anhydrous ether, lowering the temperature of the reaction to -78 C, and dropwise addition of n-BuLi (2.5M in hexane) (1.4g, 22mmol) slowly, and after the reaction was stirred for 30 minutes. After lowering the temperature of the reaction back to -78 C and dropwise added triisopropylborate (5.6g, 30mmol). Stirring at room temperature, diluted with water and it binds the 2N HCl. After the reaction was completed, the organic layer was dried and extracted with water and ethyl acetate with MgSO4 and concentrated and to the resulting organics silicagel column and recrystallized to obtain 4.2g of Sub 1(1) (yield: 73%).
70%		Intermediate 2-2 (3.9 g, 0.012 mol) was dissolved in anhydrous THF in 30 mL, a n-BuLi (2.5 M) 5.9 mL was slowly added dropwise thereto at -78 C. 1After holding for an hour, triisopropyl borate (3.4 g, 0.018 mol) was added, then stirred at room temperature for 24 hours. After completion of the reaction into a 1 N HCl after 1 hours with stirring, EA: After layer separation the H2O was recrystallized with n-Hexane < Intermediate 2-3 & gt; To give the 2.0 g (yield 70%).

References: [1]Patent: KR2015/121337,2015,A .Location in patent: Paragraph 0103; 0104; 0105; 0106.
[2]Patent: KR2016/20159,2016,A .Location in patent: Paragraph 0356; 0363-0365.

19
[ 1097884-37-1 ]
C₂₄H₁₈N₂ [ No CAS ]