352359-42-3|N-(4'-Bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine| Ambeed

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Quality Control of [ 352359-42-3 ] Purity: 97% SDS Specification

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Product Details of [ 352359-42-3 ]

CAS No. :	352359-42-3
Formula :	C₂₈H₂₀BrN
M.W :	450.37
SMILES Code :	BrC1=CC=C(C2=CC=C(N(C3=CC=CC=C3)C4=C5C=CC=CC5=CC=C4)C=C2)C=C1
MDL No. :	MFCD24387457
InChI Key :	JYAVHXABZQYLTH-UHFFFAOYSA-N
Pubchem ID :	16755312

Safety of [ 352359-42-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 352359-42-3 ]

* 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 [ 352359-42-3 ]

[ 352359-42-3 ] Synthesis Path-Downstream 1~35

1
[ 352359-42-3 ]
[ 559-40-0 ]
1,2-bis{4-[(1-naphthyl)(phenyl)amino]biphenyl}-3,3,4,4,5,5-hexafluorocyclopentene [ No CAS ]

References: [1]Molecular Crystals and Liquid Crystals,2006,vol. 444,p. 157 - 168.

2
[ 92-86-4 ]
[ 90-30-2 ]
[ 352359-42-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine; sodium t-butanolate; In toluene; at 100℃; for 24h;	To a round bottom flask Sub 1-1 (6.2g, 20mmol), Sub 1-2 (1) (4.4g, 20mmol), Pd2 (dba) 3 (0.9g, 1mmol), PPh3 (0.5g, 2mmol), NaOt -Bu (5.8g, 60mmol), were added to toluene (210mL), respectively, and refluxed under stirring for 24 hours at 100C. The organic layer was dried over MgSO4, and extracted with water and ether and recrystallized silicagel column and the resulting organics concentrated to one after the Sub 1 (1), 6.8g (Yield: 76%) was obtained.
70%	With sodium t-butanolate;1,1'-bis(diphenylphosphino)ferrocene; palladium diacetate; In toluene; at 90℃; for 15h;Inert atmosphere;	Synthesis of 4-bromo-4'-(naphthylphenylamino)biphenyl (2N); A mixture of 4,4'-dibromobiphenyl (8.46 g=27.4 mmol), Pd(OAc)2 (105 mg=0.18 mmol), dppf (253 mg=0.46 mmol), N-(1-naphthyl)aniline (2.0 g=9.13 mmol) and sodium t-butoxide (1.32 g=13.7 mmol) in dry toluene was placed in a three-necked flask under a nitrogen atmosphere and stirred at 90 C. for 15 h. After cooling, the reaction was quenched by adding water and then extracted by ethyl acetate. The organic layer was dried over anhydrous MgSO4 and evaporated under vacuum. The products were purified by a silica gel column eluted with hexane. White solid of compound 2N was obtained in 70% yield (2.86 g=6.37 mmol).The spectroscopic data of compound 2N were as follows: 1H NMR (CDCl3): δ 7.95 (d, 1H, J=7.9 Hz), 7.90 (d, 1H, J=7.9 Hz), 7.79 (d, 1H, J=8.2 Hz), 7.44-7.52 (m, 4H), 7.35-7.41 (m, 6H), 7.20-7.24 (m, 2H), 7.03-7.11 (m, 4H) and 6.97 (t, 1H, J=7.3 Hz); 13C NMR (CDCl3): δ 148.1, 147.9, 143.1, 139.5, 135.2, 132.5, 131.7, 131.2, 129.1, 128.4, 128.0, 127.4, 127.2, 126.6, 126.4, 126.3, 126.1, 124.1, 122.3, 122.1, 121.3 and 120.6; HRMS (m/z): 449.0783 (M+) (calculated value: 449.0779).
62%	With sodium t-butanolate;Pd(dppf)Cl2; In ethyl acetate; toluene;	Example 1.1.4 N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine (4): A mixture of N-phenylnaphthalen-1-amine (4.41 g, 20 mmol), 4,4'-dibromo-1,1'-biphenyl (15 g, 48 mmol), sodium tert-butoxide (4.8 g, 50 mmol) and Pd(dppf)Cl2 (0.44 g, 0.6 mmol) in anhydrous toluene (100 ml) was degassed and heated at 80 C. for 10 hours. After cooling to RT, the mixture was poured into dichloromethane (400 ml) and stirred for 30 min, then washed with brine (100 ml). The organic is collected and dried over Na2SO4, loaded on silica gel, and purified by flash column (hexanes to hexanes/ethyl acetate 90:1) to give a solid which was washed with methanol and dried under air to give a white solid 4 (5.58 g, in 62% yield).

62%	With sodium t-butanolate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In toluene; at 80℃; for 10h;	Example 1.2 Example 1.2.1 N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine CO: A mixture of N-phenylnaphthalen-1-amine (4.41 g, 20 mmol), 4,4'-dibromo-1,1'-biphenyl (15 g, 48 mmol), sodium tert-butoxide (4.8 g, 50 mmol) and Pd(dppf)Cl2 (0.44 g, 0.6 mmol) in anhydrous toluene (100 ml) was degassed and heated at 80 C. for 10 hours. After cooling to RT, the mixture was poured into dichloromethane (400 ml) and stirred for 30 min, then washed with brine (100 ml). The organic is collected and dried over Na2SO4, loaded on silica gel, and purified by flash column (hexanes to hexanes/ethyl acetate 90:1) to give a solid which was washed with methanol and dried under air to give a white solid 4 (5.58 g, in 62% yield).
62%	With sodium t-butanolate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In toluene; at 80℃; for 10h;	[0045] N-(4'-bromo-[l,l'-biphenyl]-4-yl)-N-phenylnaphthalen-l-amine (4): A mixture of N-phenylnaphthalen-1 -amine (4.41g, 20 mmol), 4,4'-dibromo- 1,1 '-biphenyl (15g, 48 mmol), sodium tert-butoxide (4.8g, 50 mmol) and Pd(dppf)Cl2 (0.44 g, 0.6 mmol) in anhydrous toluene (100 ml) was degassed and heated at 80 C for 10 hours. After cooling to RT, the mixture was poured into dichloromethane (400 ml) and stirred for 30 min, then washed with brine (100 ml). The organic is collected and dried over Na2S04, loaded on silica gel, and purified by flash column (hexanes to hexanes/ethyl acetate 90:1) to give a solid which was washed with methanol and dried under air to give a white solid 4 (5.58g, in 62% yield).
62%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate; In toluene; at 80℃; for 10h;	A mixture of N-phenylnaphthalen-i -amine (4.41 g,20 mmol), 4,4’-dibromo-i,i’-biphenyl (15 g, 48 mmol), sodium tert-butoxide (4.8 g, 50 mmol) and Pd(dppf)C12 (0.44 g, 0.6 mmol) in anhydrous toluene (100 ml) was degassed and heated at 80C. for 10 hours. After cooling to RT, the mixture was poured into dichloromethane (400 ml) and stirred for 30 mm, then washed with brine (100 ml). The organic is collected and dried over Na2 SO4, loaded on silica gel, and purified by flash colunm (hexanes to hexanes/ethyl acetate 90:1) to give a solid which was washed with methanol and dried under air to give a white solid 4 (5.58 g, in 62% yield).
62%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate; In toluene; at 80℃; for 10h;Inert atmosphere;	A mixture of N-phenylnaphthalen- i-amine (4.41 g, 20 mmol), 4,4’-dibromo-i,i’-biphenyl (15 g, 48 mmol), sodium tert-butoxide (NaOl3ut) (4.8 g, 50 mmol) and Pd(dppf)C12 (0.44 g, 0.6 mmol) in anhydrous toluene (100 mE) was degassed and heated at 800 C. for about 10 hours. After cooling to RT, the mixture was poured into dichioromethane(400 mE) and stirred for about 30 mm., then washed withbrine (100 mE). The organic solution was collected and dried over Na2SO4, loaded on silica gel, and purified by flash colunm (hexanes to hexanes/ethyl acetate 90:1) to give a solid which was washed with methanol and dried under air to givea white solid Compound 4 (5.58 g, in 62% yield).
62%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium t-butanolate; In toluene; at 80℃; for 10h;Inert atmosphere;	A mixture of N-phenylnaphthalen-i -amine (4.41 g, 20mmol), 4,4’-dibromo-i,i’-biphenyl (15 g, 48 mmol), sodiumtert-butoxide (4.8 g, 50 mmol) and Pd(dppf)C2 (0.44 g, 0.6mmol) in anhydrous toluene (100 ml) was degassed andheated at about 800 C. for about 10 hours. After cooling toRT, the mixture was poured into dichloromethane (400 ml)and stirred for about 30 mm, then washed with brine (100ml). The organic was collected and dried over Na2SO4,loaded on silica gel, and purified by flash column (hexanesto hexanes/ethyl acetate 90:1) to give a solid which waswashed with methanol and dried under air to give a whitesolid (Compound 5) (5.58 g, in 62% yield).

References: [1]Macromolecules,2005,vol. 38,p. 1640 - 1647.
[2]Patent: KR2015/117399,2015,A .Location in patent: Paragraph 0139; 0140; 0141.
[3]Tetrahedron,2009,vol. 65,p. 4726 - 4734.
[4]Patent: US2010/76205,2010,A1 .Location in patent: Page/Page column 5.
[5]Patent: US2011/140093,2011,A1 .
[6]Patent: US2011/251401,2011,A1 .Location in patent: Page/Page column 21.
[7]Patent: WO2012/88294,2012,A1 .Location in patent: Page/Page column 15.
[8]Patent: US2015/87685,2015,A1 .Location in patent: Paragraph 0112; 0113; 0114.
[9]Patent: US9172051,2015,B2 .Location in patent: Page/Page column 48; 52; 53.
[10]Patent: US9577198,2017,B1 .Location in patent: Page/Page column 63; 64; 65; 66.
[11]Patent: WO2006/73054,2006,A1 .Location in patent: Page/Page column 59.

3
[ 352359-42-3 ]
[ 134-32-7 ]
[ 352359-43-4 ]

References: [1]Macromolecules,2005,vol. 38,p. 1640 - 1647.

4
[ 352359-42-3 ]
[ 62-53-3 ]
[ 352359-41-2 ]

References: [1]Macromolecules,2005,vol. 38,p. 1640 - 1647.

5
triphenylphosphine palladium (II) chloride [ No CAS ]
[ 92-86-4 ]
[ 90-30-2 ]
[ 352359-42-3 ]

Yield	Reaction Conditions	Operation in experiment
	In 5,5-dimethyl-1,3-cyclohexadiene; water; toluene;	Under the argon gas current, 6.8 g of N-phenyl-1-naphthylamine (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 9.7 g of 4,4'-dibromobiphenyl (manufactured by Tokyo Kasei Co., Ltd.), 3 g of sodium-t-butoxide (manufactured by Hiroshima-Wako Co., Ltd.), 0.5 g of triphenylphosphine palladium (II) chloride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 500 ml of xylene were placed, and then they were reacted at 130 C. for 24 hours. After cooled it down, 1000 ml of water was added, followed by filtration of the mixture by using Celite. Then the solution obtained by the filtration was extracted by toluene, followed by drying it with the use of magnesium sulfate anhydride. After concentrating it under reduced pressure, the crude product was refined by column refining and the obtained was recrystallized by using toluene. It was separated by filtration and dried, then 4.1 g of 4'-bromo-N-phenyl-N-1-naphthyl-4-amino-1,1'-biphenyl (Intermediate 3, which will be illustrated later) was obtained.

References: [1]Patent: US2006/159957,2006,A1 .

6
[ 352359-42-3 ]
[ 13716-12-6 ]
[ 865-48-5 ]
[ 352359-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	With aniline; In toluene;	(2) Synthesis of N,N'-diphenyl-N-1-naphthylbenzidine Adding 0.66% by weight toluene solution in an amount of 100 microliter prepared by dissolving tri-t-butylphosphine into a mixed solution prepared by dissolving 4.50 g of 4-bromo-4'-(N-1-naphthyl-N-phenylamino)biphenyl, 1.11 g of aniline, 183 milligram of tris(dibenzylideneacetone)dipalladium(O) and 1.35 g of t-butoxysodium into toluene in an amount of 100 milliliter, the resultant solution was stirred at a room temperature for 5 hours. After the completion of the reaction, the solution was filtered with a use of celite and the filtrate was extracted with toluene. Concentrating the filtrate under a reduced pressure, the resultant crude product was refined by means of a column and as a result, 3.50 g of pale yellow powder was obtained

References: [1]Patent: US2007/29927,2007,A1 .

7
[ 352359-42-3 ]
[ 13716-12-6 ]
[ 865-48-5 ]
[ 923020-73-9 ]

Yield	Reaction Conditions	Operation in experiment
	With aniline; In toluene;	(2) Synthesis of 2-(N-1-naphthyl-N-phenylamino)-7-(N-phenylamino)phenanthrene Adding 0.66% by weight toluene solution in an amount of 100 microliter prepared by dissolving tri-t-butylphosphine into a mixed solution prepared by dissolving 4.74 g of 4-bromo-4'-(N-1-naphthyl-N-phenylamino)biphenyl, 1.11 g of aniline, 183 milligram of tris(dibenzylideneacetone)dipalladium(O) and 1.35 g of t-butoxysodium into toluene in an amount of 100 milliliter, the resultant solution was stirred at a room temperature for 5 hours. After the completion of the reaction, the solution was filtered. The resultant solid was washed with uses of methanol, water, methanol and toluene sequentially and further, it was dried under a reduced pressure and as a result, 3.50 g of gray powder (crude product) was obtained.

References: [1]Patent: US2007/29927,2007,A1 .

8
[ 352359-42-3 ]
[ 849146-80-1 ]

References: [1]Macromolecules,2005,vol. 38,p. 1640 - 1647.

9
[ 352359-42-3 ]
[ 849146-79-8 ]

References: [1]Macromolecules,2005,vol. 38,p. 1640 - 1647.

10
[ 352359-42-3 ]
N^4'-[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-N⁴-naphthalen-1-yl-N⁴,N^4'-diphenyl-biphenyl-4,4'-diamine [ No CAS ]

References: [1]Macromolecules,2005,vol. 38,p. 1640 - 1647.

11
[ 352359-42-3 ]
[ 849146-84-5 ]

References: [1]Macromolecules,2005,vol. 38,p. 1640 - 1647.

12
[ 352359-42-3 ]
N⁴-[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-N⁴,N^4'-di-naphthalen-1-yl-N^4'-phenyl-biphenyl-4,4'-diamine [ No CAS ]

References: [1]Macromolecules,2005,vol. 38,p. 1640 - 1647.

13
[ 352359-42-3 ]
[ 849146-83-4 ]

References: [1]Macromolecules,2005,vol. 38,p. 1640 - 1647.

14
[ 352359-42-3 ]
[ 102113-98-4 ]
C₅₂H₃₈N₂ [ No CAS ]

References: [1]Patent: WO2006/73054,2006,A1 .Location in patent: Page/Page column 73.

15
[ 352359-42-3 ]
[ 915031-05-9 ]
C₉₂H₆₆N₄ [ No CAS ]

References: [1]Patent: WO2006/120859,2006,A1 .Location in patent: Page/Page column 51-52.

16
[ 352359-42-3 ]
[ 61676-62-8 ]
[ 792909-35-4 ]

References: [1]Organometallics,2004,vol. 23,p. 5280 - 5285.

17
[ 352359-42-3 ]
[ 816421-98-4 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of 4'-(naphthylphenylamino)triphenylene-4-carbaldehyde (3N); To a three-necked round-bottom flask containing 2N (6.82 g=15.2 mmol) was added dropwise BuLi (16.1 mmol, 1.6 M in a hexane solution of 10 mL) in dry THF at -78 C., and then the solution was brought to 0 C. and stirred by a magnetic bar for 30 minutes. The solution was cooled again to -78 C. and to it was added dropwise tri-isopropyl borate (5.3 mL=19.8 mmol). The reaction solution was warmed up gradually to room temperature and stirred overnight. To the reaction solution was then added excess amount (30 mL) of 10% HCl(aq), while the mixture was stirred for another 1 hour. The reaction was quenched by pouring into distilled water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous MgSO4, and evaporation of the solvent gave a crude product, which was immediately subjected to the next reaction.The crude product was mixed with 4-bromobenzaldehyde (2.57 g=14.0 mmol), K2CO3(aq) (2.76 g=2 mmol) in 10 mL of H2O, and Pd(PPh3)4 (807 mg=0.69 mmol) in dry toluene/THF (2/1). The mixture was heated to 90 C. for 12 hours. After cooling, the products were extracted by ethyl acetate and the organic layer dried over anhydrous MgSO4. The crude product was dried in vacuo and purifies by a silica gel column eluted with CH2Cl2/hexane (1/1). Yellow solid of compound 3N was obtained in 88% yield (6.35 g=13.4 mmol).The spectroscopic data of 3N were as follows: 1H NMR (CDCl3): δ 10.04 (s, 1H), 7.93-7.95 (m, 3H), 7.88 (d, 1H, J=8.1 Hz), 7.78 (t, 3H, J=6.9 Hz), 7.67 (d, 2H, J=8.6 Hz), 7.64 (d, 2H, J=8.6 Hz), 7.44-7.50 (m, 4H), 7.35-7.38 (m, 2H), 7.24 (d, 1H, J=4.2 Hz), 7.21 (d, 2H, J=7.2 Hz), 7.10 (d, 2H, J=8.6 Hz), 7.07 (d, 2H, J=8.6 Hz) and 6.96 (t, 1H, J=7.2 Hz); 13C NMR (CDCl3): δ 191.7, 148.2, 148.0, 146.6, 143.3, 140.8, 137.6, 135.3, 135.1, 132.8, 131.3, 130.3, 129.2, 128.5, 127.7, 127.6, 127.3, 127.0, 126.7, 126.4, 124.5, 124.2, 122.4, 122.3 and 121.5; HRMS (m/z): 475.1933 (M+) (calculated value: 475.1936).

References: [1]Tetrahedron,2009,vol. 65,p. 4726 - 4734.
[2]Patent: US2010/76205,2010,A1 .Location in patent: Page/Page column 5.

18
[ 135-88-6 ]
[ 105946-82-5 ]
[ 352359-42-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 90℃; for 3h;	Synthesis Example 6: Synthesis of Intermediate 6 16.2 g (45 mmol) of 4-bromo-4'-iodo-biphenyl, 6.58 g (30 mmol) of N-phenyl-2-naphthylamine, 4.3 g (45 mmol) of t-BuONa, 0.55 g (0.6 mmol) of Pd2(dba)3, and 0.12 g (0.6 mmol) of P(t-Bu)3 were dissolved in 100 mL of toluene and stirred at 90C for 3 hours. After the reaction was completed, the reaction product was cooled to room temperature and extracted three times with distilled water and 100 ml of diethylether. An organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified using silica gel column chromatography to obtain 8.38 g (yield: 62%) of Intermediate 6. This compound was identified using HR-MS. C28H20BrN calc.: 449.0779; and found: 449.0775.

References: [1]Patent: EP2298737,2011,A1 .Location in patent: Page/Page column 29.

19
[ 352359-42-3 ]
[ 5350-57-2 ]
[ 1268622-04-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium t-butanolate;palladium diacetate; XPhos; In toluene; at 90℃; for 3h;	Synthesis Example 13: Synthesis of Intermediate 13 13.5 g (30 mmol) of Intermediate 6, 7.1 g (36 mmol) of benzophenone hydrazone, 4.3 g (45 mmol) of t-BuONa, 0.13 g (0.6 mmol) of Pd(OAc)2, and 0.29 g (0.6 mmol) of 2-dicyclohexylphosphino-2',4,6'-triisopropylbiphenyl were dissolved in 60 mL of toluene and stirred at 90C for 3 hours. The reaction product was cooled to room temperature. Distilled water was added thereto and the product was extracted twice with 100 mL of diethylether and once with 100 mL of dichloromethane. An organic layer was collected and dried using magnesium sulfate, followed by filtration. The solvent was evaporated, and the residue was separated and purified using silica gel column chromatography to obtain 15.6 g (yield: 92 %) of Intermediate 13. This compound was identified using HR-MS. C41H31N3 calc.: 565.2518; and found: 565.2522.

References: [1]Patent: EP2298737,2011,A1 .Location in patent: Page/Page column 30.

20
[ 352359-42-3 ]
[ 1268622-11-2 ]

References: [1]Patent: EP2298737,2011,A1 .

21
[ 352359-42-3 ]
[ 1268622-18-9 ]

References: [1]Patent: EP2298737,2011,A1 .

22
[ 352359-42-3 ]
[ 73183-34-3 ]
[ 792909-35-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium acetate;Pd(dppf)Cl2; In 1,4-dioxane; ethyl acetate;	Example 1.2.1 N-phenyl-N-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)naphthalen-1-amine (5): A mixture of Compound 4 (5.5 g, 12.2 mmol), bis(pinacolate)diborane (3.10 g, 12.2 mmol), Pd(dppf)Cl2 (0.446 mg, 0.6 mmol) and KOAc (5.5 g, 56 mmol) in anhydrous dioxane (60 ml) was degassed and heated at 80 C. overnight. After being cooled to RT, the mixture was poured into ethyl acetate (200 ml), washed with brine (150 ml). The organic solution was dried over Na2SO4, loaded on silica gel and purified by flash column (hexanes to hexanes/ethyl acetate 30:1) to collect the major fraction. After removal of solvent, the solid was washed with methanol, filtered and dried in air to give a white solid 5 (5.50 g, in 90% yield).
90%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃;	Example 1.2.2 N-phenyl-N-(4'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-4-yl)naphthalen-1-amine (7): A mixture of Compound 6 (5.5 g, 12.2 mmol), bis(pinacolate)diborane (3.10 g, 12.2 mmol), Pd(dppf)Cl2 (0.446 mg, 0.6 mmol) and KOAc (5.5 g, 56 mmol) in anhydrous dioxane (60 ml) was degassed and heated at 80 C. overnight. After being cooled to RT, the mixture was poured into ethyl acetate (200 ml), washed with brine (150 ml). The organic solution was dried over Na2SO4, loaded on silica gel and purified by flash column (hexanes to hexanes/ethyl acetate 30:1) to collect the major fraction. After removal of solvent, the solid was washed with methanol, filtered and dried in air to give a white solid 7 (5.50 g, in 90% yield).
90%	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃;	Example 1.2.14 5[0047] N-phenyl-N-(4'-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-[l,l'- biphenyl]-4-yl)naphthalen-l-amine (5): A mixture of Compound 4( 5.5 g, 12.2 mmol), bis(pinacolate)diborane (3.10 g, 12.2 mmol), Pd(dppf)Cl2 (0.446 mg, 0.6 mmol) and KOAc (5.5 g, 56 mmol) in anhydrous dioxane (60 ml) was degassed and heated at 80 C overnight. After being cooled to RT, the mixture was poured into ethyl acetate (200 ml), washed with brine (150 ml). The organic solution was dried over Na2S04, loaded on silica gel and purified by flash column (hexanes to hexanes/ethyl acetate 30:1) to collect the major fraction. After removal of solvent, the solid was washed with methanol, filtered and dried in air to give a white solid 5 (5.50g, in 90% yield).

90%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃;	A mixture of Compound 6 (5.5 g, 12.2 mmol), bis (pinacolate)diborane (3.10 g, 12.2 mmol), Pd(dppf)C12 (0.446 mg, 0.6 mmol) and KOAc (5.5 g, 56 mmol) in anhydrous dioxane (60 ml) was degassed and heated at 80 C. overnight. After being cooled to RT, the mixture was poured into ethyl acetate (200 ml), and washed with brine (150 ml). The organic solution was dried over Na2504, loaded on silica gel and purified by flash column (hexanes to hexanes/ethyl acetate 30:1) to collect the major fraction. After removal of solvent, the solid was washed with methanol, filtered and dried in air to give a white solid 7 (5.50 g, in 90% yield).
90%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃;Inert atmosphere;	Amixture of Compound 4(5.5 g, i2.2 mmol), bis(pinacolate)diborane (3.10 g, i2.2 mmol), Pd(dppf)C12 (0.446 mg,0.6 mmol) and KOAc (5.5 g, 56 mmol) in anhydrous dioxane(60 mE) was degassed and heated at about 80 C. overnight.After being cooled to RT, the mixture was poured into ethyl acetate (200 mE), and washed with brine (150 mE). The organic solution was dried over Na2SO4, loaded on silica gel and purified by flash column (hexanes to hexanes/ethyl acetate 30:1) to collect the major fraction. After removal ofsolvent, the solid was washed with methanol, filtered and dried in air to give a white solid CompoundS (5.50 g, in 90% yield).
90%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃;Inert atmosphere;	A mixture of Compound 5 (5.5 g, 12.2 mmol), bis(pinacolate)diborane (3.10 g, 12.2 mmol), Pd(dppf)C12(0.446 mg, 0.6 mmol) and KOAc (5.5 g, 56 mmol) inanhydrous dioxane (60 ml) was degassed and heated atabout 80 C. overnight. After being cooled to RT, themixture was poured into ethyl acetate (200 ml) and washedwith brine (150 ml). The organic solution was dried overNa2SO4, loaded on silica gel and purified by flash colunm(hexanes to hexanes/ethyl acetate 30:1) to collect the majorfraction. After removal of solvent, the solid was washed withmethanol, filtered and dried in air to give a white solid (5.50g, in 90% yield).

References: [1]Patent: US2011/140093,2011,A1 .
[2]Patent: US2011/251401,2011,A1 .Location in patent: Page/Page column 21-22.
[3]Patent: WO2012/88294,2012,A1 .Location in patent: Page/Page column 16.
[4]Patent: US2015/87685,2015,A1 .Location in patent: Paragraph 0112; 0115; 0116.
[5]Patent: US9172051,2015,B2 .Location in patent: Page/Page column 48; 53; 54.
[6]Patent: US9577198,2017,B1 .Location in patent: Page/Page column 63; 64; 65; 66.

23
[ 352359-42-3 ]
[ 912637-92-4 ]

References: [1]Patent: US2011/140093,2011,A1 .
[2]Patent: US2011/251401,2011,A1 .
[3]Patent: US2015/87685,2015,A1 .

24
[ 352359-42-3 ]
[ 1339153-88-6 ]

References: [1]Patent: US2011/251401,2011,A1 .
[2]Patent: US2015/87685,2015,A1 .

25
[ 352359-42-3 ]
[ 1311407-98-3 ]

References: [1]Patent: WO2012/88294,2012,A1 .

26
[ 352359-42-3 ]
[ 1146340-38-6 ]
[ 1311407-97-2 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃;	Example 1.1.5[0046] Host-1: A mixture of Compound 3 (0.80 g, 2mmol), Compound 4 (0.90, 2mmol), tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4) (0.115g, 0.1 mmol) and potassium carbonate (0.69g, 5 mmol) in dioxane/water (25 ml/5 ml) was degassed and heated at 100 C overnight. After cooling down to RT, the mixture was worked up with water and ethyl acetate (150 ml x 3). The organic phase is collected and dried over Na2S04, loaded on silica gel, purified by flash column (hexanes/ethyl acetate 8:1 to 6:1) to give an off white solid (Host-1) (0.90 g, in 70% yield). LCMS data: calcd for C47H34N3 (M+H) = 640.3; found: m/e=640.

References: [1]Patent: WO2012/88294,2012,A1 .Location in patent: Page/Page column 15-16.

27
[ 352359-42-3 ]
N-phenyl-N-(4’-(6’-(1-phenyl-1H-benzo[d]imidazol-2-yl)-[2,3’-bipyridin]-5-yl)-[1,1’-biphenyl]-4-yl)naphthalen-2-amine [ No CAS ]

References: [1]Patent: US9172051,2015,B2 .

28
[ 352359-42-3 ]
N-phenyl-N-(4’-(6-(1-phenyl-1H-benzo[d]imidazol-2-yl)pyridin-3-yl)-[1,1’-biphenyl]-4-yl)naphthalen-1-amine [ No CAS ]

References: [1]Patent: US9172051,2015,B2 .

29
[ 352359-42-3 ]
C₂₈H₁₄⁽²⁾H₇N [ No CAS ]
C₅₆H₃₃⁽²⁾H₇N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triphenylphosphine; sodium t-butanolate; In toluene; at 100℃; for 24h;	To a round bottom flask Sub 1(1) (9.0g, 20mmol), Sub 2(28) (7.6g, 20mmol), Pd2(dba)3 (0.9g, 1mmol), PPh3 (0.5g, 2mmol), NaOt-Bu (5.8g, 60mmol), were added to toluene (210mL), respectively, and refluxed under stirring for 24 hours at 100C. The organic layer was dried and the ether was extracted with water over MgSO4 and concentrated and to the resulting organic silicagel column and recrystallized to form a 2-4 11.8g (yield: 79%).

References: [1]Patent: KR2015/117399,2015,A .Location in patent: Paragraph 0183; 0184; 0185.

30
[ 108-86-1 ]
[ 352359-42-3 ]

References: [1]Patent: KR2015/117399,2015,A .

31
[ 134-32-7 ]
[ 352359-42-3 ]

References: [1]Patent: KR2015/117399,2015,A .

32
[ 352359-42-3 ]
[ 1267248-54-3 ]
C₆₇H₄₉N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 110℃; for 3h;Inert atmosphere;	The compound 10.0 g (18.99 mmol), synthesized under thenitrogen air current in the preparation example 19 N -(4'-bromo-(1,1'-biphenyl)-4-yl) -N-phenylnaphthalen-1-amine of 8.55 g (18.99mmol), the Pd 2 (dba) 3 of 0.52 g (0.57 mmol), P (t-bu) 3 of0.38 g (1.90 mmol), and the NaO (t-bu) and toluene (200 ml) of 4.56 g(47.47 mmol) were mixed and it was stirred in 110 for 3hours. It extracted in the dichloromethane after the reactiontermination and the MgSO 4 was put and it filtered. Theintended compound 11.06 g (yield: 62 %) was obtained using the columnchromatography after the solvent of the filtered organic layer was removed

References: [1]Patent: KR2016/12500,2016,A .Location in patent: Paragraph 0413-0415.

33
[ 352359-42-3 ]
N-(4-(9H-carbazol-9-yl)phenyl)-9,9-diphenyl-9H-fluoren-2-amine [ No CAS ]
C₇₁H₄₉N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 110℃; for 3h;Inert atmosphere;	The compound 10.0 g (17.40 mmol), synthesized under thenitrogen air current in the preparation example 28 N -(4'-bromo-(1,1'-biphenyl)-4-yl) -N-phenylnaphthalen-1-amine of 7.84 g (17.40mmol), the Pd 2 (dba) 3 of 0.48 g (0.52 mmol), P (t-bu) 3 of0.35 g (1.74 mmol), and the NaO (t-bu) and toluene (200 ml) of 4.18 g(43.50 mmol) were mixed and it was stirred in 110 for 3hours. It extracted in the dichloromethane after the reactiontermination and the MgSO 4 was put and it filtered. Theintended compound 11.50 g (yield: 70 %) was obtained using the columnchromatography after the solvent of the filtered organic layer was removed

References: [1]Patent: KR2016/12500,2016,A .Location in patent: Paragraph 0449-0451.

34
[ 352359-42-3 ]
N-(4-(9H-carbazol-9-yl)phenyl)-9,9'-spirobi[fluoren]-2-amine [ No CAS ]
C₇₁H₄₇N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 110℃; for 3h;Inert atmosphere;	The compound 10.0 g (17.46 mmol), synthesized under thenitrogen air current in the preparation example 29 N -(4'-bromo-(1,1'-biphenyl)-4-yl) -N-phenylnaphthalen-1-amine of 7.86 g (17.46mmol), the Pd 2 (dba) 3 of 0.48 g (0.52 mmol), P (t-bu) 3 of0.35 g (1.75 mmol), and the NaO (t-bu) and toluene (200 ml) of 4.20 g(43.65 mmol) were mixed and it was stirred in 110 for 3hours. It extracted in the dichloromethane after the reactiontermination and the MgSO 4 was put and it filtered. Theintended compound 13.33 g (yield: 81 %) was obtained using the columnchromatography after the solvent of the filtered organic layer was removed

References: [1]Patent: KR2016/12500,2016,A .Location in patent: Paragraph 0481-0483.

35
[ 352359-42-3 ]
N-(4-(9H-carbazol-9-yl)phenyl)-9,9-dimethyl-9H-fluoren-2-amine [ No CAS ]
C₆₁H₄₅N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 110℃; for 3h;Inert atmosphere;	The compound 10.0 g (22.19 mmol), synthesized under the nitrogen air current in the preparation example 12 N - (4'-bromo-(1,1'-biphenyl)-4-yl) -N-phenylnaphthalen-1-amine of 10.00 g (22.19 mmol), the Pd 2 (dba) 3 of 0.61 g (0.67 mmol), P (t-bu) 3 of 0.45 g (2.22 mmol), and the NaO (t-bu) and toluene (200 ml) of 5.33 g (55.49 mmol) were mixed and it was stirred in 110 for 3hours. It extracted in the dichloromethane after the reaction termination and the MgSO 4 was put and it filtered. The intended compound 14.74 g (yield: 76 %) was obtained using the column chromatography after the solvent of the filtered organic layer was removed

References: [1]Patent: KR2016/12500,2016,A .Location in patent: Paragraph 0357-0359.

Historical Records

Technical Information

• Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • Hydrogenolysis of Benzyl Ether • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Vilsmeier-Haack Reaction

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CAS No.: 352359-42-3

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CAS No.: 352359-42-3

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