[ CAS No. 22034-43-1 ] {[proInfo.proName]}

Name: 22034-43-1|9-(Naphthalen-1-yl)-9H-carbazole|97%
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SKU: A578736
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Quality Control of [ 22034-43-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 22034-43-1 ]

CAS No. :	22034-43-1	MDL No. :	MFCD26127424
Formula :	C₂₂H₁₅N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QSOAYCUFEQGHDN-UHFFFAOYSA-N
M.W :	293.36	Pubchem ID :	626218
Synonyms :

Calculated chemistry of [ 22034-43-1 ]

Physicochemical Properties

Num. heavy atoms :	23
Num. arom. heavy atoms :	23
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	98.29
TPSA :	4.93 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.3
Log Po/w (XLOGP3) :	6.25
Log Po/w (WLOGP) :	5.94
Log Po/w (MLOGP) :	5.12
Log Po/w (SILICOS-IT) :	5.08
Consensus Log Po/w :	5.14

Druglikeness

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

Water Solubility

Log S (ESOL) :	-6.27
Solubility :	0.000157 mg/ml ; 0.000000537 mol/l
Class :	Poorly soluble
Log S (Ali) :	-6.14
Solubility :	0.000212 mg/ml ; 0.000000724 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-8.32
Solubility :	0.00000141 mg/ml ; 0.0000000048 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.73

Safety of [ 22034-43-1 ]

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

Application In Synthesis of [ 22034-43-1 ]

* 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.

Upstream synthesis route of [ 22034-43-1 ]
Downstream synthetic route of [ 22034-43-1 ]

[ 22034-43-1 ] Synthesis Path-Upstream 1~7

1
[ 90-11-9 ]
[ 86-74-8 ]
[ 22034-43-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With copper(l) iodide; 18-crown-6 ether; potassium carbonate In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) at 170 - 180℃; for 13.5 h;	[Embodiment 8]; [0397]In this embodiment, a synthetic method of2-{iV-(l-naphthyl)-iV-[9-(l-naphthyl)carbazol-3-yl]ammo}-9,10-diphenylanthracene (abbreviation: 2NCNPA), which is the anthracene derivative of the present invention represented by Structural Formula (220), is specifically described. ; [0398] <n="170"/>[0399][Step 1] Synthesis of N^-d^l-naphthyl^H-carbazole-S-amine (abbreviation: NCN)[0400](i) Synthesis of 9-(l-naphthyl)carbazole.A synthetic scheme of 9-(l-naphthyl)carbazole is shown in (C-18). [0401]CuI, 18-crown-6-ether, K₂CO₃, DMPU (C-18)[0402] 21 g (0.1 mol) of 1-bromonaphthalene, 17 g (0.1 mol) of carbazole, 950 mg (5 mmol) of copper iodide (I), 33 g (240 mmol) of potassium carbonate, and 660 mg (2.5 mmol) of 18-crown-6-ether were put into a 500 mL three-neck flask, and nitrogen substitution was carried out in the flask. To this mixture was added 80 mL of l,3-dimethyl-3,4,5,6-tetrahydro-2(l/-T)-pyrimidinone (abbreviation: DMPU), which was <n="171"/>followed by stirring for 6 hours at 170 ⁰C under nitrogen. To this reaction mixture was further added 10 g (50 mmol) of 1-bromonaphthalene, 2.0 g (10 mmol) of copper iodide (I), and 2.6 g (10 mmol) of 18-crown-6-ether, and stirring was further conducted for 7.5 hours at 170 ⁰C. Furthermore, to this reaction mixture was added 10 g (50 mmol) of 1-bromonaphthalene, and additional stirring was carried out for 6 hours at 180⁰C. After the reaction was completed, to this reaction mixture was added about 200 mL of toluene and about 100 mL of 1 mol/L hydrochloric acid, and then the mixture was filtered through celite. The obtained filtrate was filtered through Florisil and celite. The obtained filtrate was separated into an organic layer and an aqueous layer, and after this organic layer was washed with 1 mol/L hydrochloric acid and then with water, the organic layer was dried over magnesium sulfate. This suspension was filtered through Florisil and celite. The filtrate was concentrated to give an oily -substrate, and methanol was added to this oily substrate, followed by irradiation with ultrasound to precipitate a solid. The solid precipitated was collected by suction filtration, giving 22 g of 9-(l-naphthyl)carbazole as white powder (75percent yield). The Rf values (SiO₂, eluent; hexane:ethyl acetate = 10:1) of 9-(l-naphthyl)carbazole, 1-bromonaphthalene, and carbazole were 0.61, 0.74, and 0.24, respectively.
75%	With 18-crown-6 ether; potassium carbonate In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 170 - 180℃; for 19.5 h;	Step 1: Synthesis of 9-(l-naphthyl)-9H-carbazole][0700]A synthetic scheme of 9-(l-naphthyl)-9H-carbazole in Step 1 is shown in the following (R-I). [0701][0702]In a 500-mL three-neck flask, 21 g (100 mmol) of 1-bromonaphthalene, 17 g (100 mmol) of carabazole, 0.1 g (5.0 mmol) of copper(I) iodide, 0.7 g (2.5 mmol) of 18-crown-6-ether, 33 g (240 mmol) of potassium carbonate, and 80 mL of l,3-dimethyl-3,4,5,6-tetrahydro-2(lH)pyrimidinone (abbreviation: DMPU) were put, <n="239"/>and the mixture was stirred under a nitrogen atmosphere at 170 ⁰C for 6 hours. Then, 10 g (50 mmol) of 1-bromonaphthalene, 2.0 g (10 mmol) of copper(I) iodide, and 2.6 g (10 mmol) of 18-crown-6-ether were further added to this reaction mixture, and the mixture was further stirred at 170 ⁰C for 7.5 hours. After that, 10 g (50 mmol) of 1-bromonaphthalene was further added to this reaction mixture, and the mixture was further stirred at 180 ⁰C for 6 hours. [0703]After the reaction, about 200 mL of toluene and about 100 mL of hydrochloric acid (1 mol/L) were added to this reaction mixture, and the mixture was filtered through Celite. The obtained filtrate was filtrated through Florisil and Celite. The obtained filtrate was separated into an organic layer and an aqueous layer. After this organic layer was washed with hydrochloric acid (1 mol/L) and water in this order, magnesium sulfate was added to remove moisture. This suspension was filtered through Florisil and Celite. Then, hexane was added to the oily substance obtained by concentrating the obtained filtrate, and the mixture was irradiated with supersonic and then recrystallized to obtain 22 g of an objective white powder at a yield of 75 percent.

Reference： [1] Patent: WO2007/125934, 2007, A1, . Location in patent: Page/Page column 168-169
[2] Patent: WO2009/72587, 2009, A1, . Location in patent: Page/Page column 237-238
[3] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2006, vol. 63, # 1, p. 15 - 20
[4] Journal of Organic Chemistry, 2009, vol. 74, # 9, p. 3341 - 3349

2
[ 90-14-2 ]
[ 86-74-8 ]
[ 22034-43-1 ]

Reference： [1] New Journal of Chemistry, 2017, vol. 41, # 2, p. 559 - 568
[2] Organic Letters, 2015, vol. 17, # 14, p. 3640 - 3642

3
[ 134-32-7 ]
[ 13029-08-8 ]
[ 22034-43-1 ]

Reference： [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 9, p. 1954 - 1960

4
[ 13029-09-9 ]
[ 134-32-7 ]
[ 22034-43-1 ]

Reference： [1] Advanced Synthesis and Catalysis, 2010, vol. 352, # 4, p. 616 - 620

5
[ 189999-35-7 ]
[ 134-32-7 ]
[ 22034-43-1 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 1202 - 1209

6
[ 2113-51-1 ]
[ 22034-43-1 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2013, vol. 9, p. 1202 - 1209

7
[ 623-03-0 ]
[ 90-11-9 ]
[ 1413355-67-5 ]
[ 22034-43-1 ]
[ 57103-17-0 ]

Reference： [1] Science, 2012, vol. 338, # 6107, p. 647 - 651

[ 22034-43-1 ] Synthesis Path-Downstream 1~18

1
[ 90-11-9 ]
[ 86-74-8 ]
[ 22034-43-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With tris-(dibenzylideneacetone)dipalladium(0); di?tert?butyl(2',6'?dimethoxy?[1,1'?biphenyl]?2?yl)phosphane; lithium hexamethyldisilazane; In 5,5-dimethyl-1,3-cyclohexadiene; toluene; at 140℃; for 15.0h;Inert atmosphere;	Under argon atmosphere,In a reaction vessel, 167 mg (1.0 mmol) of 9H-carbazole,4.6 mg (5.0 mumol) of tris (dibenzylideneacetone) dipalladium,as well as2-di (tert-butyl) phosphino-2,6-dimethoxy-1,1'-biphenyl12.5mg (35mumol)Is suspended in 5.0 mL of xylene,Here lithium bis (trimethylsilyl) amide (LiHMDS) HM1.0M-toluene solution 1.1mL (1.1mmol)And 1-bromonaphthalene 311 mg (1.5 mmol) were added.Heat this mixture to 140 C.Stir for 15 hours.After cooling to room temperature,25 mL of water and 20 mL of ethyl acetate were added to the reaction mixture.Collect 0.1 mL of the organic layer,After diluting with 3.0 mL of tetrahydrofuran and analyzing by HPLC,It was confirmed that 95% of 9- (1-naphthyl) -9H-carbazole was formed.The reaction solution was extracted three times with 25 mL of ethyl acetate, and the organic layer was washed with saturated saline. The organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 30/1 (volume ratio)) to give 9- (1-naphthyl) -9H-carbazole was obtained as a white solid (275 mg, 94%).
75%	With copper(l) iodide; 18-crown-6 ether; potassium carbonate; In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU); at 170 - 180℃; for 13.5h;	[Embodiment 8]; [0397]In this embodiment, a synthetic method of2-{iV-(l-naphthyl)-iV-[9-(l-naphthyl)carbazol-3-yl]ammo}-9,10-diphenylanthracene (abbreviation: 2NCNPA), which is the anthracene derivative of the present invention represented by Structural Formula (220), is specifically described. ; [0398] <n="170"/>[0399][Step 1] Synthesis of N^-d^l-naphthyl^H-carbazole-S-amine (abbreviation: NCN)[0400](i) Synthesis of 9-(l-naphthyl)carbazole.A synthetic scheme of 9-(l-naphthyl)carbazole is shown in (C-18). [0401]CuI, 18-crown-6-ether, K2CO3, DMPU (C-18)[0402] 21 g (0.1 mol) of 1-bromonaphthalene, 17 g (0.1 mol) of carbazole, 950 mg (5 mmol) of copper iodide (I), 33 g (240 mmol) of potassium carbonate, and 660 mg (2.5 mmol) of 18-crown-6-ether were put into a 500 mL three-neck flask, and nitrogen substitution was carried out in the flask. To this mixture was added 80 mL of l,3-dimethyl-3,4,5,6-tetrahydro-2(l/-T)-pyrimidinone (abbreviation: DMPU), which was <n="171"/>followed by stirring for 6 hours at 170 0C under nitrogen. To this reaction mixture was further added 10 g (50 mmol) of 1-bromonaphthalene, 2.0 g (10 mmol) of copper iodide (I), and 2.6 g (10 mmol) of 18-crown-6-ether, and stirring was further conducted for 7.5 hours at 170 0C. Furthermore, to this reaction mixture was added 10 g (50 mmol) of 1-bromonaphthalene, and additional stirring was carried out for 6 hours at 1800C. After the reaction was completed, to this reaction mixture was added about 200 mL of toluene and about 100 mL of 1 mol/L hydrochloric acid, and then the mixture was filtered through celite. The obtained filtrate was filtered through Florisil and celite. The obtained filtrate was separated into an organic layer and an aqueous layer, and after this organic layer was washed with 1 mol/L hydrochloric acid and then with water, the organic layer was dried over magnesium sulfate. This suspension was filtered through Florisil and celite. The filtrate was concentrated to give an oily -substrate, and methanol was added to this oily substrate, followed by irradiation with ultrasound to precipitate a solid. The solid precipitated was collected by suction filtration, giving 22 g of 9-(l-naphthyl)carbazole as white powder (75% yield). The Rf values (SiO2, eluent; hexane:ethyl acetate = 10:1) of 9-(l-naphthyl)carbazole, 1-bromonaphthalene, and carbazole were 0.61, 0.74, and 0.24, respectively.
75%	With 18-crown-6 ether; potassium carbonate;copper(l) iodide; In 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; at 170 - 180℃; for 19.5h;	Step 1: Synthesis of 9-(l-naphthyl)-9H-carbazole][0700]A synthetic scheme of 9-(l-naphthyl)-9H-carbazole in Step 1 is shown in the following (R-I). [0701][0702]In a 500-mL three-neck flask, 21 g (100 mmol) of 1-bromonaphthalene, 17 g (100 mmol) of carabazole, 0.1 g (5.0 mmol) of copper(I) iodide, 0.7 g (2.5 mmol) of 18-crown-6-ether, 33 g (240 mmol) of potassium carbonate, and 80 mL of l,3-dimethyl-3,4,5,6-tetrahydro-2(lH)pyrimidinone (abbreviation: DMPU) were put, <n="239"/>and the mixture was stirred under a nitrogen atmosphere at 170 0C for 6 hours. Then, 10 g (50 mmol) of 1-bromonaphthalene, 2.0 g (10 mmol) of copper(I) iodide, and 2.6 g (10 mmol) of 18-crown-6-ether were further added to this reaction mixture, and the mixture was further stirred at 170 0C for 7.5 hours. After that, 10 g (50 mmol) of 1-bromonaphthalene was further added to this reaction mixture, and the mixture was further stirred at 180 0C for 6 hours. [0703]After the reaction, about 200 mL of toluene and about 100 mL of hydrochloric acid (1 mol/L) were added to this reaction mixture, and the mixture was filtered through Celite. The obtained filtrate was filtrated through Florisil and Celite. The obtained filtrate was separated into an organic layer and an aqueous layer. After this organic layer was washed with hydrochloric acid (1 mol/L) and water in this order, magnesium sulfate was added to remove moisture. This suspension was filtered through Florisil and Celite. Then, hexane was added to the oily substance obtained by concentrating the obtained filtrate, and the mixture was irradiated with supersonic and then recrystallized to obtain 22 g of an objective white powder at a yield of 75 %.

73%	With tris-(dibenzylideneacetone)dipalladium(0); N,N?-bis(2,6-bis(diphenylmethyl)-4-methoxyphenyl)imidazol-2-ylidene; lithium hexamethyldisilazane; In 5,5-dimethyl-1,3-cyclohexadiene; toluene; at 140℃; for 15.0h;Inert atmosphere; Sealed tube;Catalytic behavior;	The reaction procedure in run 17 in Table 1 is used as a representative example in the amination with LiHMDS. 9H-carbazole 2 (167 mg, 1.0 mmol), Pd2(dba)3 (13.7 mg, 15 lmol), and IPr*OMe (37.8 mg, 40 mumol) were added to a 10 mL reaction vessel, and Ar gas was thoroughly flushed. After the addition of dehydrated and degassed xylene (3 mL) under an Ar stream, 1.1mL of toluene solution of LiHMDS (1.0 mol/L) was added dropwise. Next, 1a (207 mg, 1.0 mmol) was added to the reaction mixture and the vessel was sealed and heated at 140 C for 15 h. Subsequent HPLC analysis and the isolation procedure described above gave 3 as a white solid (213 mg, 73% yield). 9-(1-naphthyl)-9H-carbazole (3): 1H NMR (400 MHz, CDCl3) delta 6.98-7.03 (2H, m), 7.26-7.37 (6H, m), 7.54 (1H, ddd, J = 1.5, 6.6, 8.2 Hz), 7.62-7.70 (2H, m), 8.02 (1H, d. J = 8.3 Hz), 8.03-8.07 (1H, m), 8.19-8.23 (2H, m). 13C NMR (400 MHz, CDCl3) delta 110.22, 119.76, 120.31, 123.21, 123.53, 125.93, 126.72, 126.76, 126.96, 128.46, 129.02, 130.95, 134.05, 134.87, 142.18. Compounds 5, 7, and 9 were isolated in the same manner.
73%	With tris-(dibenzylideneacetone)dipalladium(0); N,N?-bis(2,6-bis(diphenylmethyl)-4-methoxyphenyl)imidazol-2-ylidene; lithium hexamethyldisilazane; In 5,5-dimethyl-1,3-cyclohexadiene; toluene; at 140℃; for 15.0h;Inert atmosphere;	167 mg (1.0 mmol) of 9H-carbazole in a reaction vessel,Tris (dibenzylideneacetone) dipalladium {13.7 mg (15 mumol) and N, N?-bis [2,6-bis (diphenylmethyl) -4-methoxyphenyl) imidazole-2-ylideneAfter adding 37.8 mg (40 mumol), the inside of the reaction system was replaced with argon gas. After adding 3.0 mL of xylene, 1.1 mL of a 1.0 M solution of LiHMDS in toluene (1.1 mmol of LiHMDS) was added dropwise. Further, 1-bromonaphthalene 207 mg (1. 0 mmol), heated to 140 C. and stirred for 15 hours. After cooling to room temperature, water (25 mL) was added to stop the reaction. 20 mL of ethyl acetate was added, and the mixture was stirred until the ethyl acetate layer became uniform. Ethyl acetate layer 0.1 mL was collected and tetrahydrofuran 3.0 mAfter dilution with L, HPLC analysis confirmed that 78% of 9- (1-naphthalenyl) -9H-carbazole was produced.[0065]The reaction solution was extracted three times with 25 mL of ethyl acetate, and the organic layer was washed with saturated saline. The organic layer was dehydrated by adding anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 30/1 (volume ratio)).9- (1-Naphthalenyl) -9H-carbazole was obtained as a white solid (213 mg, 73%).

Reference： [1]Patent: JP2019/196323,2019,A .Location in patent: Paragraph 0041-0051; 0066-0069
[2]Patent: WO2007/125934,2007,A1 .Location in patent: Page/Page column 168-169
[3]Patent: WO2009/72587,2009,A1 .Location in patent: Page/Page column 237-238
[4]Synthetic Communications,2019,vol. 49,p. 159 - 165
[5]Patent: JP2019/196324,2019,A .Location in patent: Paragraph 0062-0066
[6]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2006,vol. 63,p. 15 - 20
[7]Journal of Organic Chemistry,2009,vol. 74,p. 3341 - 3349

2
[ 22034-43-1 ]
[ 68-12-2 ]
[ 119471-79-3 ]

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2006,vol. 63,p. 15 - 20

3
[ 22034-43-1 ]
[ 934545-83-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With N-Bromosuccinimide; In ethyl acetate; toluene; at 20℃; for 170.0h;	[0403] (ii) Synthesis of 3-bromo-9~(l-naphthyl)carbazole.; A synthetic scheme of 3-bromo-9-(l-naphthyl)carbazole is shown in (C-19).[0404]NBS, Toluene, Ethyl acetate (C-19)[0405]5.9 g (20 mmol) of 9-(l-naphthyl)carbazole was put into a 500 mL Meyer flask, <n="172"/>and 50 mL of ethyl acetate and 50 mL of toluene were added thereto, and the reaction mixture was stirred. Then, 3.6 g (20 mmol) of iV-bromosuccinimide was slowly added to the solution, and the solution was stirred for about 170 hours (one week) at room temperature. After this solution was washed with water, the organic layer was dried with magnesium sulfate. Filtration and concentration of the reaction mixture gave 7.4 g of 3-bromo-9-(l-naphthyl)carbazole as white powder (99% yield). The Rf values (SiO2, eluent; hexane: ethyl acetate = 2:1) of 3-bromo-9-(l-naphthyl)carbazole and 9-(l-naphthyl)carbazole were 0.43 and 0.35, respectively. [0406] ?
99%	With N-Bromosuccinimide; In ethyl acetate; toluene; at 20℃; for 170.0h;	Step 2: Synthesis of 3-bromo-9-(l-naphthyl)-9H-carbazole] [0706]A synthetic scheme of 3-bromo-9-(l-naphthyl)-9H-carbazole in Step 2 is shown in the following (R-2). [0707][0708] <n="240"/>After 5.9 g (20 mmol) of 9-(l-naphthyl)-9H-carbazole was dissolved in a mixture solvent of 50 mL of toluene and 50 mL of ethyl acetate in a 500-mL conical flask, 3.6 g (20 mmol) of iV-bromo succinimide (abbreviation: NBS) was added to this solution. After that, this mixture was stirred at room temperature for 170 hours. After completion of the reaction, this mixture solution was washed with water, and magnesium sulfate was added thereto to remove moisture. This mixture solution was filtrated, and the obtained filtrate was concentrated and dried to obtain 7.4 g of an objective white powder at a yield of 99 %.
99%	With N-Bromosuccinimide; In ethyl acetate; toluene; at 20℃; for 36.0h;	Example 6; In this example, an example in which 9-(1-naphthyl)-3-[4-(1-naphthyl)-phenyl]-9H-carbazole (abbreviation: NCPN) represented by Structural Formula (120) in Embodiment 1 is manufactured will be described. Step 1: Synthesis Method of 3-bromo-<strong>[22034-43-1]9-(1-naphthyl)-9H-carbazole</strong>In a 200-mL conical flask, 5.9 g (20 mmol) of <strong>[22034-43-1]9-(1-naphthyl)-9H-carbazole</strong> was dissolved in a mixture solvent of 50 mL of toluene and 70 mL of ethyl acetate, and then 3.6 g (20 mmol) of N-bromosuccinimide (abbreviation: NBS) was added to this solution. The mixture was stirred at room temperature for 36 hours. After completion of the reaction, this mixture solution was washed with water, and magnesium sulfate was added thereto so that moisture was adsorbed. This suspension was filtrated, and the obtained filtrate was concentrated and collected. As a result, 7.4 g of white powder that was an objective substance was obtained in a yield of 99%. The synthesis scheme of Step 1 is shown in (F6-1).

Reference： [1]Patent: WO2007/125934,2007,A1 .Location in patent: Page/Page column 169-170
[2]Patent: WO2009/72587,2009,A1 .Location in patent: Page/Page column 238-239
[3]Patent: US2012/77987,2012,A1 .Location in patent: Page/Page column 49-50

4
[ 22034-43-1 ]
2,5-bis{3'-[3''-vinyl-9''-(α-naphthyl)carbazolyl]phenyl}-1,3,4-oxadiazole [ No CAS ]

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,2006,vol. 63,p. 15 - 20

5
[ 22034-43-1 ]
[ 929103-28-6 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 3341 - 3349

6
[ 13029-09-9 ]
[ 134-32-7 ]
[ 22034-43-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 616 - 620

7
[ 22034-43-1 ]
[ 1369431-26-4 ]

Reference： [1]Patent: US2012/77987,2012,A1

8
[ 623-03-0 ]
[ 90-11-9 ]
[ 1413355-67-5 ]
[ 22034-43-1 ]
[ 57103-17-0 ]

Reference： [1]Science,2012,vol. 338,p. 647 - 651

9
[ 189999-35-7 ]
[ 134-32-7 ]
[ 22034-43-1 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1202 - 1209

10
[ 2113-51-1 ]
[ 22034-43-1 ]

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1202 - 1209

11
[ 134-32-7 ]
[ 13029-08-8 ]
[ 22034-43-1 ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 1954 - 1960

12
[ 90-14-2 ]
[ 86-74-8 ]
[ 22034-43-1 ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 559 - 568
[2]Organic Letters,2015,vol. 17,p. 3640 - 3642

13
[ 22034-43-1 ]
3,6-diiodo-9-(1-naphthyl)carbazole [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 559 - 568

14
[ 22034-43-1 ]
[ 1219692-16-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With bis-[(trifluoroacetoxy)iodo]benzene; In 1,2-dichloro-ethane; at 20℃; for 0.5h;	General procedure: PIFA (0.75 equiv.) was added to a stirred solution of the appropriatenaphthalenamine 1 (0.30 mmol, 1 equiv) in DCE (3 mL) atr.t., and the mixture was stirred for 30 min. When the reactionwas complete, sat. aq NaHCO3 was added to the mixture, andthe aqueous phase was extracted with CH2Cl2. The extractswere dried (Na2SO4) and evaporated to dryness, and the cruderesidue was purified by column chromatography (silica gel,hexane-EtOAc).

Reference： [1]Synlett,2017,vol. 28,p. 2941 - 2945

15
[ 86-74-8 ]
[ 90-13-1 ]
[ 22034-43-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	With tris-(dibenzylideneacetone)dipalladium(0); di?tert?butyl(2',6'?dimethoxy?[1,1'?biphenyl]?2?yl)phosphane; lithium tert-butoxide; In 5,5-dimethyl-1,3-cyclohexadiene; at 140℃; for 15.0h;Inert atmosphere; Sealed tube;Catalytic behavior;	The procedure in run 7 in Table 1 is used as a representative example of the amination with LiOtBu. 9H-carbazole 2 (167 mg, 1.0 mmol), Pd2(dba)3 (4.6 mg, 5.0 mumol), tBu-SPhos (12.5 mg, 35 mumol), and LiOtBu (120 mg, 1.5 mmol) were added to a 10mL reaction vessel and Ar gas was thoroughly flushed through the vessel. After the addition of dry and degassed xylene (3 mL) and 1b (163 mg, 1.0 mmol) under an Ar stream, the vessel was sealed and heated at 140 C for 15 h. Subsequently, the reaction mixture was cooled to room temperature and quenched by the addition of water (25 mL). The organic compounds were completely dissolved by the addition of ethyl acetate (20 mL) and stirring. After the addition of 100 mg of 3,6-dibromo-9-phenyl-9H-carbazole as an internal standard to the obtained water-ethyl acetate mixture, 0.1mL of the ethyl acetate phase was diluted with 3mL of THF. The analysis of 3 muL of this THF solution using HPLC revealed the formation of 3 in 95% yield. The products were extracted three times from the water-ethyl acetate mixture by adding ethyl acetate (25 mL). The ethyl acetate layer was washed with sat. NaCl aq. solution (20 mL) and dried over Na2SO4. The solvent was then removed under vacuum and the residue was purified by passing through a silica gel column (eluent: hexane/ethyl acetate =30/1) giving 3 as a white solid (275 mg, 94% yield).
94%	With tris-(dibenzylideneacetone)dipalladium(0); di?tert?butyl(2',6'?dimethoxy?[1,1'?biphenyl]?2?yl)phosphane; lithium tert-butoxide; In 5,5-dimethyl-1,3-cyclohexadiene; toluene; at 140℃; for 15.0h;Inert atmosphere;	In a reaction vessel, 167 mg (1.0 mmol) of 9H-carbazole, 4.6 mg (5.0 mumol) of tris (dibenzylideneacetone) dipalladium, 2-di (tert-butyl) phosphino-2 ?, 6?-dimethoxy-1, 1?-biphenyl 12.5 mg (35 mumol),And 120 mg (1.5 mmol) of lithium-tert-butoxide, and then the inside of the reaction system was replaced with argon gas. After adding 3.0 mL of xylene, 163 mg (1.0 mmol) of 1-chloronaphthalene was further added, and the mixture was heated to 140 C. and stirred for 15 hours. After cooling to room temperature, 25 mL of water was added to stop the reaction. 20 mL of ethyl acetate was added, and the mixture was stirred until the ethyl acetate layer became uniform. 0.1 mL of the ethyl acetate layer was collected, diluted with 3.0 mL of tetrahydrofuran, and then analyzed by HPLC.9- (1-naphthyl) -9H-carbazole is 95% based on the charged 9H-carbazoleConfirmed that it was generated.The reaction solution was extracted three times with 25 mL of ethyl acetate, and the organic layer was washed with saturated saline. The organic layer was dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 30/1 (volume ratio)) to give 9- (1-naphthyl) -9H-carbazole was obtained as a white solid (295 mg, 94%).
83%	With tris-(dibenzylideneacetone)dipalladium(0); N,N?-bis(2,6-bis(diphenylmethyl)-4-methoxyphenyl)imidazol-2-ylidene; lithium hexamethyldisilazane; In 5,5-dimethyl-1,3-cyclohexadiene; toluene; at 140℃; for 15.0h;Inert atmosphere;	General procedure: 167 mg (1.0 mmol) of 9H-carbazole in a reaction vessel,Tris (dibenzylideneacetone) dipalladium {13.7 mg (15 mumol) and N, N?-bis [2,6-bis (diphenylmethyl) -4-methoxyphenyl) imidazole-2-ylideneAfter adding 37.8 mg (40 mumol), the inside of the reaction system was replaced with argon gas. After adding 3.0 mL of xylene, 1.1 mL of a 1.0 M solution of LiHMDS in toluene (1.1 mmol of LiHMDS) was added dropwise. Further, 1-bromonaphthalene 207 mg (1. 0 mmol), heated to 140 C. and stirred for 15 hours. After cooling to room temperature, water (25 mL) was added to stop the reaction. 20 mL of ethyl acetate was added, and the mixture was stirred until the ethyl acetate layer became uniform. Ethyl acetate layer 0.1 mL was collected and tetrahydrofuran 3.0 mAfter dilution with L, HPLC analysis confirmed that 78% of 9- (1-naphthalenyl) -9H-carbazole was produced.[0065]The reaction solution was extracted three times with 25 mL of ethyl acetate, and the organic layer was washed with saturated saline. The organic layer was dehydrated by adding anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography (eluent: hexane / ethyl acetate = 30/1 (volume ratio)).9- (1-Naphthalenyl) -9H-carbazole was obtained as a white solid (213 mg, 73%).

Reference： [1]Synthetic Communications,2019,vol. 49,p. 159 - 165
[2]Patent: JP2019/196323,2019,A .Location in patent: Paragraph 0052-0060
[3]Patent: JP2019/196324,2019,A .Location in patent: Paragraph 0062-0065; 0068-0069

16
[ 22034-43-1 ]
[ 434-45-7 ]
[ 2838092-57-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With trifluoroacetic acid at 80℃; Sealed tube; regioselective reaction;

Reference： [1]Ma, Feng; Wu, Xian-Tao; Miao, Le-Wei; Sun, Fuxing; Jiang, Yi-Jun; Chen, Peng [Advanced Synthesis and Catalysis, 2022, vol. 364, # 20, p. 3477 - 3482]

17
[ 22034-43-1 ]
[ 395-01-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
65%	With trifluoroacetic acid at 80℃; Sealed tube; regioselective reaction;

Reference： [1]Ma, Feng; Wu, Xian-Tao; Miao, Le-Wei; Sun, Fuxing; Jiang, Yi-Jun; Chen, Peng [Advanced Synthesis and Catalysis, 2022, vol. 364, # 20, p. 3477 - 3482]

18
[ 22034-43-1 ]
[ 2902743-26-2 ]

Yield	Reaction Conditions	Operation in experiment
58 %	With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide at 25℃; Inert atmosphere; Irradiation; Schlenk technique;	General procedure for BCN-catalysed photoredox dearomative hydrogenation (condition A) General procedure: Photocatalytic dearomatization was performed in a Schlenk flask(10 ml). The temperature of the reaction solution was maintained at 298 K by a flow of circulating water connected to thermocontrol devices. The reaction was carried out by dispersing 10 mg of BCN powder in a solution that contained H2O (0.3 ml), DMF (1 ml), substrate(0.10 mmol, 1.0 equiv.) and DIPEA (0.20 mmol, 2.0 equiv.). The Schlenk flask was degassed with a vacuum pump and backfilled with N2 (1 bar).Then the reaction mixture was stirred and irradiated using a 450 nm(±10 nm) LEDs for 24 h. After the reaction, the mixture was filtered and then transferred to a separatory funnel. Brine (10 ml) was added and the mixture was extracted with AcOEt (3 × 10 ml). The combined organic fractions were washed with fresh brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SG using petroleum ether-ethyl acetate as the eluent to afford the final product.
58 %	With water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; Inert atmosphere; Irradiation; Schlenk technique;	General procedure for BCN-catalysed photoredox dearomative hydrogenation (condition A) General procedure: Photocatalytic dearomatization was performed in a Schlenk flask(10 ml). The temperature of the reaction solution was maintained at 298 K by a flow of circulating water connected to thermocontrol devices. The reaction was carried out by dispersing 10 mg of BCN powder in a solution that contained H2O (0.3 ml), DMF (1 ml), substrate(0.10 mmol, 1.0 equiv.) and DIPEA (0.20 mmol, 2.0 equiv.). The Schlenk flask was degassed with a vacuum pump and backfilled with N2 (1 bar).Then the reaction mixture was stirred and irradiated using a 450 nm(±10 nm) LEDs for 24 h. After the reaction, the mixture was filtered and then transferred to a separatory funnel. Brine (10 ml) was added and the mixture was extracted with AcOEt (3 × 10 ml). The combined organic fractions were washed with fresh brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SG using petroleum ether-ethyl acetate as the eluent to afford the final product.

Reference： [1]Yuan, Tao; Sun, Luyang; Wu, Ziwei; Wang, Rong; Cai, Xu; Lin, Wei; Zheng, Meifang; Wang, Xinchen [Nature Catalysis, 2022, vol. 5, # 12, p. 1157 - 1168]
[2]Yuan, Tao; Sun, Luyang; Wu, Ziwei; Wang, Rong; Cai, Xu; Lin, Wei; Zheng, Meifang; Wang, Xinchen [Nature Catalysis, 2022, vol. 5, # 12, p. 1157 - 1168]

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[ 22034-43-1 ] Synthesis Path-Upstream 1~7

[ 22034-43-1 ] Synthesis Path-Downstream 1~18

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Aryls

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Carbazole Series

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