Name: 90-30-2|N-Phenyl-1-naphthylamine|98%
Brand: Ambeed
SKU: A812108
Price: 13.0 USD
Availability: InStock
Rating: 90 (26 reviews)

1
[ 90-30-2 ]
[ 59935-39-6 ]
bis-(4-anilino-[1]naphthyl)-(4-dimethylamino-3-nitro-phenyl)-methane [ No CAS ]

Reference： [1]Noelting [Bulletin de la Societe industrielle de Mulhouse, vol. 72, p. 229][Chemische Berichte, 1904, vol. 37, p. 1912]

2
[ 90-30-2 ]
[ 13338-49-3 ]
(4,5-dihydro-1H-imidazol-2-ylmethyl)-[1]naphthyl-phenyl-amine; hydrochloride [ No CAS ]

Reference： [1]Helvetica Chimica Acta,1950,vol. 33,p. 1386,1403

3
[ 90-30-2 ]
[ 6341-40-8 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; sodium nitrite

Reference： [1]Fischer,O.; Hepp [Chemische Berichte, 1887, vol. 20, p. 1248]

4
[ 591-50-4 ]
[ 90-30-2 ]
[ 603-34-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	In various solvent(s) at 160℃; for 8h;

Reference： [1]Paine, Anthony James [Journal of the American Chemical Society, 1987, vol. 109, # 5, p. 1496 - 1502]

5
[ 82-76-8 ]
[ 90-30-2 ]

Reference： [1]Journal of the American Chemical Society,1983,vol. 105,p. 6236 - 6243
[2]Journal of the American Chemical Society,1983,vol. 105,p. 6236 - 6243

6
[ 624-38-4 ]
[ 90-30-2 ]
[ 38257-52-2 ]

Reference： [1]Journal of the American Chemical Society,1987,vol. 109,p. 1496 - 1502

7
[ 696-62-8 ]
[ 90-30-2 ]
[ 4316-51-2 ]

Reference： [1]Journal of the American Chemical Society,1987,vol. 109,p. 1496 - 1502

8
[ 90-30-2 ]
[ 51927-78-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	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]Journal of Organic Chemistry,2017,vol. 82,p. 8958 - 8972
[2]Organic Letters,2011,vol. 13,p. 4950 - 4953
[3]Synlett,2017,vol. 28,p. 2941 - 2945
[4]Journal of Organic Chemistry,2006,vol. 71,p. 1351 - 1361
[5]Journal of Organic Chemistry,1985,vol. 50,p. 541 - 543

9
[ 130-14-3 ]
[ 62-53-3 ]
[ 90-30-2 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1980,vol. 16,p. 2014 - 2016
Zhurnal Organicheskoi Khimii,1980,vol. 16,p. 2356 - 2358

10
[ 92-86-4 ]
[ 90-30-2 ]
[ 123847-85-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: N-phenyl-1-naphthylamine With n-butyllithium Stage #2: 4-(4-bromophenyl)bromobenzene With bis[tris(2-methylphenyl)phosphine]palladium In toluene at 100℃;
92%	With palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate In o-xylene at 120℃; for 3h;

Reference： [1]Maiti; Wang; Cheng; Huang; Chao [Journal of the Chinese Chemical Society, 2001, vol. 48, # 6 A, p. 1059 - 1064]
[2]Yamamoto, Toshihide; Nishiyama, Masakazu; Koie, Yasuyuki [Tetrahedron Letters, 1998, vol. 39, # 16, p. 2367 - 2370]

11
[ 90-30-2 ]
[ 37002-45-2 ]
(2S,3S)-2,3-O-isopropylidene-4-α-naphthyl(phenyl)amino-1-O-tosylbutane-1,2,3-triol [ No CAS ]

Reference： [1]European Journal of Inorganic Chemistry,2000,p. 351 - 358

12
[ 4805-22-5 ]
[ 90-30-2 ]
N,N'-diphenyl-N,N'-bis(1-naphthyl)-5,5'-diamino-2,2'-bithiophene [ No CAS ]

Reference： [1]Chemical Communications,2001,p. 1628 - 1629
[2]Synthesis,2002,p. 2487 - 2489
[3]Chemical Communications,2002,p. 1530 - 1531

13
[ 90-30-2 ]
[ 186259-63-2 ]
N,N'-di-naphthalen-1-yl-9,9,N,N'-tetraphenyl-9H-fluorene-2,7-diamine [ No CAS ]

Reference： [1]Organic Letters,2001,vol. 3,p. 2285 - 2288

14
[ 33255-13-9 ]
[ 90-30-2 ]
(6-bromo-9-ethyl-9H-carbazol-3-yl)-naphthalen-1-yl-phenyl-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With (t-Bu)3; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 80℃;

Reference： [1]Justin Thomas; Lin; Tao; Ko [Journal of the American Chemical Society, 2001, vol. 123, # 38, p. 9404 - 9411]

15
[ 21792-52-9 ]
[ 62-53-3 ]
[ 90-30-2 ]
[ 92855-12-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 42% 2: 35%	With [(tris(1-pyrazolyl)borate)Ru(P(phenyl)3)(CH₃CN)2]PF₆ at 100℃; for 15h;

Reference： [1]Odedra, Arjan; Wu, Chang-Jung; Pratap, Taduri Bhanu; Huang, Chun-Wei; Ran, Ying-Fen; Liu, Rai-Shung [Journal of the American Chemical Society, 2005, vol. 127, # 10, p. 3406 - 3412]

16
[ 439791-57-8 ]
[ 90-30-2 ]
2,7-bis[(N-naphthalenyl)phenylamino]-(2',7'-di-tert-butyl)-9,9'-spirobifluorene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate In toluene Heating;

Reference： [1]Shen, Jiun Yi; Lee, Chung Ying; Huang, Tai-Hsiang; Lin, Jiann T.; Tao, Yu-Tai; Chien, Chin-Hsiung; Tsai, Chiitang [Journal of Materials Chemistry, 2005, vol. 15, # 25, p. 2455 - 2463]

17
[ 134-32-7 ]
[ 108-90-7 ]
[ 90-30-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	In ethanol; for 6h;Reflux;	To a solution of naphthalen-1-amine (1.0 g, 6.98 mmol) in ethanol(3 mL), chlorobenzene (0.783 g, 6.98 mmol) was added, and the resultingmixture was refluxed for 6 h. The reaction progress was monitoredby TLC (dichloromethane/methanol, 9.5:0.5 vol). After completionof the reaction, solvent was evaporated and the mixture waspurified by column chromatography on silica using dichloromethaneand dichloromethane/methanol (99:1), as the eluent. N-phenylnaphthalen-1-amine 2b was obtained as pink solid (1.357 g, yield88%). Mp 59-61 C. Rf=0.40 (dichloromethane/methanol,9.0:1.0 vol): 1H NMR (CDCl3, 400 MHz): deltaH 6.81 (dd, J=6.8 and1.6 Hz, 2 H, 2-H and 4-H Ph), 7.32-7.41 (m, 4 H, 3-H Ph, 5-H Ph, 2-H Phand 6-H Ph), 7.48-7.54 (m, 3 H, 4-H, 6-H, 3-H), 7.82-7.89 (m, 3 H, 7-H,5-H and 8-H) ppm. 13C NMR (CDCl3, 100.6 MHz): deltaC 109.61 (C-2 and1×Ar-C), 118.89 (2×Ar-C), 120.74 (2×Ar-C), 123.59 (C-8a),124.78 (1×Ar-C), 125.78 (1×Ar-C), 126.28 (3×ArC), 128.48(1×Ar-C), 134.33 (C-4a and C-1 Ph), 142.02 (C-1) ppm.
65%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 110℃; for 5h;Inert atmosphere;	(1) Add compound A-33 (100 mmol) to the reaction vessel,After compound B-33 (110 mmol) and 300 mL of toluene,Add Pd2 (dba) 3 (1.1mmol) under nitrogen atmosphere,P (t-Bu) 3 (5.5mmol), t-BuONa (220mmol),Next, the reaction temperature was slowly raised to 110 C,And the mixture was stirred for 5 hours for reaction;Then, distilled water was added to the reaction solution and the reaction solution was extracted with ethyl acetate;Then, the extracted organic layer was dried using magnesium sulfate,And use a rotary evaporator to remove the solvent,Purify the remaining material by column chromatography to obtain intermediate C-33(14.2g, yield 65%, MW: 219.10).

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 1619 - 1623
[2]Dyes and Pigments,2020,vol. 173
[3]Synlett,2012,vol. 23,p. 2333 - 2336
[4]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1967 - 1973
[5]Synlett,2005,p. 275 - 278
[6]Patent: CN111004201,2020,A .Location in patent: Paragraph 0057-0061

18
[ 62-53-3 ]
[ 90-13-1 ]
[ 90-30-2 ]

Yield	Reaction Conditions	Operation in experiment
72%		General procedure: A mixture of substrate 2 (0.5 mmol), 1 (0.6 mmol), Pd(OAc)2 (2 mol%), Xphos (4 mol%), NaOtBu (2.0 equiv.) and Na2SO4 (2.0 g) were added to the 25 mL screw-capped stainless-steel vessel, along with two stainless steel balls ( = 1.4 cm). After that, the vessel was placed in the mixer mill, and the contents were ball milled at 30 Hz for 60 min. At the end of the reaction, small portion (3 mL) ethyl acetate and (3 mL) H2O were added in to the vessel and grinding for another 2 min at 30 Hz. Then, after the washing by brine, the organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give a residue, which was purified by flash column chromatography on silica gel to give the desired product.

Reference： [1]Dalton Transactions,2018,vol. 47,p. 8690 - 8696
[2]Journal of Organic Chemistry,2006,vol. 71,p. 1351 - 1361
[3]Tetrahedron Letters,2018,vol. 59,p. 2277 - 2280
[4]European Journal of Organic Chemistry,2014,vol. 2014,p. 2070 - 2076

19
[ 33255-13-9 ]
[ 90-30-2 ]
9-ethyl-N,N'-dinaphthalen-1-yl-N,N'-diphenyl-9H-carbazole-3,6-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With (t-Bu)3; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 80℃;

Reference： [1]Justin Thomas; Lin; Tao; Ko [Journal of the American Chemical Society, 2001, vol. 123, # 38, p. 9404 - 9411]

20
[ 90-30-2 ]
[ 57103-20-5 ]
N3,N6-di(naphthalene-1-yl)-N3,N6,9-triphenyl-9H-carbazole-3,6-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In tetrahydrofuran; toluene; at 100℃; for 36h;	Procedure for Synthesis of Compounds 7c. A mixture of3,6-dibromo-9H-carbazole 4 (1.0 g, 2.5 mmol), N-phenyl-naphthalen-1-amine 5 (1.6 g, 7.3 mmol), Pd(OAc)2(0.15 g, 0.67 mmol), t-Bu3P 50percent in toluene (0.5 mL,2.2 mmol), and NaOtBu 2 M in THF (5.0 mL, 47.4 mmol)in 100 mL of dry toluene was stirred at 100C for 36 h. After completion of the reaction, the mixture was extractedwith dichloromethane. The organic layer was separated,dried over magnesium sulfate, ltered, and evaporated. Theresidue was puried by silica gel column chromatographyusing n-hexane: dichloromethane as the eluent to givedesigned compounds 7c.N3,N6-di(naphthalene-1-yl)-N3,N6,9-triphenyl-9H-carba-zole-3,6-diamine (7c). Yield: 78percent; yellow solid; 1H NMR(500 MHz, CDCl3) delta8.08?8.06 (d, J = 8.0Hz, 2H),7.89?7.88 (d, J = 8.0Hz, 2H), 7.8 (s, 2H), 7.74?7.73 (d,J = 8.0Hz, 2H), 7.60?7.55 (q, J1 = 7.5Hz, J2 = 15.0Hz,4H), 7.47?7.44 (m, 5H), 7.37?7.34 (q, J1 = 7.5Hz,J2 = 15.0 Hz, 4H), 7.31?7.25 (m, 4H), 7.16?7.13 (t,J = 8Hz, 4H), 6.89?6.84 (q, J1 = 8.0Hz, J2 = 15.0Hz, 6H);13C NMR (125 MHz, CDCl3) delta183.6, 179.2, 171.3, 168.4,160.1, 159.7, 141.5, 135.3, 129.0, 128.4, 128.2, 127.5,127.2, 126.8, 126.0, 125.0, 124.6, 120.5, 119.7, 110.7; GC-MS: 668.23 for C50H35N3 [M + H+].

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 9404 - 9411
[2]Bulletin of the Korean Chemical Society,2016,vol. 37,p. 1710 - 1716

21
[ 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): delta 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): delta 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).

Reference： [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

22
[ 90-30-2 ]
[ 4181-20-8 ]
[ 185690-39-5 ]

Yield	Reaction Conditions	Operation in experiment
60%	With copper; potassium carbonate; In decalin; at 220℃; for 24h;	Compound 5; 4,4',4-tris[(1-naphtyl)phenylamino]tripnenylamine; 28.7 g (0.046 moles) of 4,4',4-triiodotriphenylamine, 50.4 g (0.23 moles) of N-(1-naphtyl)aniline, 44.2 g (0.32 moles) of anhydrous potassium carbonate, 4.32 g (0.068 moles) of copper powders and 50 ml of decalin were added to a reaction container of 200 ml, and the mixture was heated in an oil bath at 220° C. for 24 hours in an argon atmosphere. After completion of the reaction, 200 ml of toluene was added to the reaction product, followed by filtering to remove the insoluble. The filtrate was washed with water, and dried on sodium sulfate. After drying, the solvent was evaporated from the filtrate, and the residue was purified four times on a column chromatography using silica gel as a carrier and a mixture of n-hexane and toluene as a developing solvent. The recrystallization process was repeated using a mixture of n-hexane and toluene and ethyl acetate, followed by vacuum drying. 24.7 g (yield: 60.0percent) of 4,4',4-tris[(1-naphtyl)phenylamino]tripnenylamine was obtained. The resulting product was further purified by sublimation to obtain a high purity 4,4',4-tris[(1-naphtyl)phenylamino]tripnenylamine (yield of sublimation purification: 70.0percent).

Reference： [1]Patent: US2007/293704,2007,A1 .Location in patent: Page/Page column 17-18

23
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.

Reference： [1]Patent: US2006/159957,2006,A1

24
[ 589-87-7 ]
[ 90-30-2 ]
copper [ No CAS ]
[ 865-48-5 ]
[ 110-70-3 ]
[ 138310-84-6 ]

Yield	Reaction Conditions	Operation in experiment
	In 5,5-dimethyl-1,3-cyclohexadiene;	(1) Synthesis of N-(4-bromophenyl)-N-phenyl-1-naphthylamine Adding 17.6 g of N,N'-dimethylethylenediamine into a solution prepared by mixing 21.9 g of N-phenyl-1-naphthylamine, 28.2 g of 4-bromoiodobenzene, 14.4 g of t-butoxysodium, 3.81 g of copper powder and 100 milliliter of xylene, the resultant solution was refluxed with heating under ambient atmosphere of argon gas for 24 hours. After cooling the resultant solution down to a room temperature, the solution was filtered and insolubles were removed followed by concentrating the filtrate. Refining the residue by means of a silicagel column chromatography, 25.4 g of N-(4-bromophenyl)-N-phenyl-1-naphthylamine was obtained.

Reference： [1]Patent: US2007/29927,2007,A1

25
[ 90-30-2 ]
[ 18733-91-0 ]
[ 948584-98-3 ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium phosphate at 240℃; for 48h;

Reference： [1]Bai, Dong-Ren; Liu, Xiang-Yang; Wang, Suning [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5713 - 5723]

26
[ 90-30-2 ]
[ 18733-98-7 ]
C₅₆H₄₀Br₂N₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With potassium phosphate at 230℃; for 48h;

Reference： [1]Bai, Dong-Ren; Liu, Xiang-Yang; Wang, Suning [Chemistry - A European Journal, 2007, vol. 13, # 20, p. 5713 - 5723]

27
[ 90-30-2 ]
[ 123847-85-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 0 °C 1.2: 53 percent / tetrahydrofuran; hexane / 18 h / 20 °C 2.1: 35 percent / P(t-Bu)3; Cs₂CO₃; CsF / Pd₂dba3; scCO₂ / hexane / 48 h / 100 °C / 93086.6 Torr
	Multi-step reaction with 2 steps 1: sodium sulfate; potassium carbonate; copper / nitrobenzene 2: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triphenylphosphine; sodium t-butanolate / toluene / 24 h / 100 °C

Reference： [1]Smith, Catherine J.; Tsang, Melanie W.S.; Holmes, Andrew B.; Danheiser, Rick L.; Tester, Jefferson W. [Organic and Biomolecular Chemistry, 2005, vol. 3, # 20, p. 3767 - 3781]
[2]Current Patent Assignee: DUK SAN NEOLUX CO., LTD. - KR2015/31892, 2015, A

28
[ 3001-15-8 ]
[ 90-30-2 ]
4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.9%	With copper; potassium carbonate;PEG-6000; at 200 - 250℃; for 12h;Heating / reflux; Neat (no solvent);	(Synthetic Example 4) N,N'-diphenyl-bis(1-naphthyl)-4,4'-diaminobiphenyl (alpha-NPD) was synthesized as follows. 25.1g (61.5mmol) of 4,4'-diiodobiphenyl, 2.14g of poly(ethylene glycol) PEG-6000 that was available from Wako Pure Chemical Industries, Ltd., 17.1g (0.124mol) of potassium carbonate and 15.7g (247mmol) of powdered copper were added to 32.4g (148mmol) of <strong>[90-30-2]N-phenyl-1-naphthylamine</strong>. It was heated at 200 degrees Centigrade. It was determined for tracing by the high-speed liquid chromatography. And it was stirred and refluxed for 12 hours until no peaks of starting materials and intermediates were determined. DMF and water were added thereto to disperse. It was filtrated and washed with water. Precipitated crystals were purified by silica gel column chromatography to obtain 20.2g of alpha-NPD that is represented by Compound Example 4 at 55.9% yield. Incidentally, when the similar procedures of Synthetic Example 4 were executed except for using 1.57g of powdered copper and heating at 250 degrees Centigrade, the same alpha-NPD was obtained.
45.0%	With copper; potassium carbonate; In nitrobenzene; at 195 - 210℃; for 20h;	N,N'-di(1-naphtyl)-N,N'-diphenylbenzidine 4.6 g (0.021 moles) of (1-naphtyl)phenylamine, 4.06 g (0.01 mole) of 4,4'-diiodobiphenyl, 2.90 g (0.021 moles) of anhydrous potassium carbonate, 0.32 g (0.005 moles) of copper powders and 10 ml of nitrobenzene were mixed, and the mixture was reacted at 195 to 210 C. for 20 hours. The reaction product was extracted with 140 ml of toluene, the insoluble was filtered off, and the filtrate was concentrated. 120 ml of n-hexane was added to the concentrated product to obtain a raw product. The raw product was purified on a column chromatography using silica gel as a carrier and toluene/n-hexane (1/2) as an eluding solution to obtain 2.6 g (yield: 45.0%) of N,N'-di(1-naphtyl)-N,N'-diphenylbenzidine.

Reference： [1]Bulletin of the Korean Chemical Society,2011,vol. 32,p. 2461 - 2464
[2]Patent: JP2005/162671,2005,A .Location in patent: Page/Page column 11
[3]Patent: EP1553079,2005,A2 .Location in patent: Page/Page column 12
[4]Patent: US2007/293704,2007,A1 .Location in patent: Page/Page column 18
[5]Molecular Crystals and Liquid Crystals,2009,vol. 498,p. 314 - 322

29
[ 90-30-2 ]
[ 138310-84-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;bis-triphenylphosphine-palladium(II) chloride; In xylene; at 130℃; for 12h;	Mixed under argon flow were 259 g of N-phenyl-1-naphthylamine (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 279 g of 4-dibromobenzene (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 136 g of sodium t-butoxide (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 17 g of bis(triphenylphosphine)palladium dichloride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) and 4.6 liter of xylene, and they were reacted at 130C for 12 hours. Water was added to the reaction liquid, and the mixture was filtered through celite, followed by carrying out separation thereof with toluene. The oil layer was concentrated under reduced pressure to obtain crystal. This was refined through a column and then dissolved in toluene, and hexane was added thereto to reprecipitate crystal. It was filtered and then dried to obtain 135 g of N-(4-bromophenyl)-N-phenyl-1-naphthylamine (B1).

Reference： [1]Patent: EP1559706,2005,A1 .Location in patent: Page/Page column 38

30
[ 728039-63-2 ]
[ 90-30-2 ]
N,N,N'-triphenyl-4-amino-N'-(1-naphthyl)-amino-1,1'-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;bis-triphenylphosphine-palladium(II) chloride; In xylene; at 130.0℃; for 24h;	Under a stream of argon, 2.3 g of 4'-bromo-N,N-dibiphenylyl-4-amino-1,1'-biphenyl obtained in Example 2 (1), 1 g of N-phenyl-1-naphthylamine (manufactured by TOKYO KASEI KOGYO Co., Ltd.), 0.5 g of sodium t-butoxide (manufactured by HIROSHIMA WAKO Co., Ltd.), 0.1 g of bis(triphenylphosphine)palladium(II) chloride (manufactured by TOKYO KASEI KOGYO Co., Ltd.) and 300 ml of xylene were placed into a reactor, and the reaction was allowed to proceed at 130C for 24 hours. After the reaction mixture was cooled, 500 ml of water was added, and the resultant mixture was filtered through a Celite filter. The filtrate was treated by extraction with toluene and dried with anhydrous magnesium sulfate. The resultant solution was concentrated under a reduced pressure, and the obtained crude product was purified in accordance with the column chromatography and recrystallized from toluene. The formed crystals were separated by filtration and dried, and 2.0 g of a light yellow powder obtained. The obtained powder was analyzed in accordance with the FD-MS analysis and identified to be N,N,N'-triphenyl-4-amino-N'-(1-naphthyl)-amino-1,1'-biphenyl (H4) since the main peak was found at m/z=690, which corresponded to C52H38N2=690.

Reference： [1]Patent: EP1584614,2005,A1 .Location in patent: Page/Page column 21

31
[ 474687-62-2 ]
[ 90-30-2 ]
C₅₄H₃₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium t-butanolate;palladium diacetate; tri-tert-butyl phosphine; In o-xylene; at 130℃; for 3h;	To a suspension of Chemical Compound 1 (1.50 g, 2.68 mmol), N-phenyl-1-naphtylamine (0.59 g, 2.68 mmol), and sodium t-butoxide (0.31 g, 3.22 mmol) in o-xylene (20 ml), Pd(OAc)2 (0.2 mg, 0.007 mmol) and P(t-Bu)3 (0.50 mg, 0.003 mmol) were added. After the reaction mixture had been stirred at 130 C. for 3 hours, it was cooled to room temperature, quenched with water (40 ml), and extracted with dichloromethane (3×40 ml). The combined organic extracts were dried over MgSO4 and concentrated under vacuum. Purification by recrystallization from chloroform and ethanol afforded Chemical Compound 301 (1.50 g, 80%) as white solid: mp 370.4 C.; 1H NMR (500 MHz, DMSO-d6) delta 8.03 (d, J=7.3 Hz, 2H), 7.88 (dd, J=7.8, 8.5 Hz, 3H), 7.76 (d, J=8.3 Hz, 1H), 7.44-7.32 (m, 11H), 7.26 (m, 4H), 7.19 (dt, J=1.0, 8.3 Hz, 1H), 7.03 (dd, J=1.0, 7.3 Hz, 1H), 6.86-6.80 (m, 4H), 6.71 (t, J=7.3 Hz, 1H), 6.38 (d, J=7.8 Hz, 2H), 6.24-6.21 (m, 2H), 6.16 (dd, J=2.8, 8.7 Hz, 1H), 6.13 (d, J=2.3 Hz, 1H), 6.06 (d, J=8.7 Hz, 1H); MS (M+) calculated for C54H35N 697. found 696. analysis calculated for C54H35N: C, 92.94; H, 5.06; N, 2.01. Found: C, 93.05; H, 4.91; N, 2.04.

Reference： [1]Patent: US6998487,2006,B2 .Location in patent: Page/Page column 53-54

32
[ 29558-77-8 ]
[ 90-30-2 ]
[ 896427-52-4 ]

Yield	Reaction Conditions	Operation in experiment
74%		A suspension of Pd2(dba)3 (1.48 g, 1.61 mmol) and 2-(dicyclohexylphosphino)biphenyl (1.36 g, 3.87 mmol) in THF (30 mL) is stirred for 30 minutes. To this is added <strong>[29558-77-8]4-bromo-4'-hydroxybiphenyl</strong> (8.04 g, 32.3 mmol), N-phenyl-1- napthylamine (14.16 g, 65.6 mmol) and LiN(SiMe3)2 (11 -89 g, 71.0 mmol) with THF (70 mL) and the mixture refluxed for five days after which time it is filtered through silica and washed with brine, drying the organic phase over magnesium sulfate. Upon evaporation a dark red viscous solid is obtained which is purified by chromatography on silica (EtOAc/hex) to afford a pale orange powder (9.2 g, 74%). The product was confirmed by NMR analysis.

Reference： [1]Patent: WO2006/72002,2006,A2 .Location in patent: Page/Page column 16-17; 23-24

33
[ 589-87-7 ]
[ 90-30-2 ]
[ 138310-84-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In toluene; at 100℃; for 12h;Inert atmosphere;	General procedure: General procedure for the palladium-catalyzed reaction A solution of Pd(OAc)2 (0.8 mg, 0.0036 mmol), Xantphos (2.1 mg, 0.0036 mmol), NaOtBu (51 mg, 0.53 mmol), 1-bromo-4-iodobenzene (1a) (100 mg, 0.35 mmol), and N,N-diphenylamine (2a) (72 mg, 0.43 mmol) in toluene (0.5 mL) was stirred at 100 C for 12 h. The reaction was quenched with H2O, and extracted with CH2Cl2 (3*3 mL). The chemoselectivity (3aa/4aa=92/8) was measured by HPLC analysis using Inertsil ODS-3V. The pure monoaminated product 3aa (99 mg, 86%) was obtained by flash chromatography (hexane/CH2Cl2=97/3) as a white solid.
88%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate; In toluene; at 85℃; for 2h;	1-bromo-4-sulfonate host compound (1.41g, 5mmol), intermediates 13-B (1.10g, 5 mmol), Pd2(dba)3(0.09 g, 0.1 mmol),t-Bu3P (0.02 g, 0.1 mmol) andt-BuOK (0.56 g, 5.0 mmol) in 85 C is toluene 75 ml to adaptation stirring time senses a rotation velocity of the disk 2. Said reaction solution down to the normal temperature 50 ml to 30 parts by weight of diethyl ether and a 50 ml water after being cool off, extracted burn 3. The organic layer collected dry magnesium sulfate anhydride obtained for vaporizing the solvent residue is silica gel tube chromatography for purifying 13-A intermediate that is (1.65g, 88% yield) is obtained. It is found out that to the resulting compound is LC-MS. C22H16BrN M+ computed value: 374.05, measurements: 374.28)
80.4%	With tri-tert-butyl phosphine; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; for 12h;Heating;	1Og of N-phenylnaphthalene-1-amine (leq, 0.046mol) and 14.3g of l-bromo-4-iodobenzene (l.leq, 0.05mol) were dissolved in 150ml of toluene in a flask. 0.27g of Pd2(dba)3 (0.03eq, 3mmol) , 10.5g of Na(t-Bu)O (l.leq, 0.05mol), and O.lg of P(t-Bu)3 (O.Obetaeq, O.betammol) were added to the mixture solution respectively, and then the resultant mixture solution was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through celite, and then 13.4g of N- (4-bromophenyl) - N-phenylnaphthalene-1-amine was obtained from the filtrate through column chromatography (yield 80.4%).GC-Mass (theoretical value: 373.05g/mol, measured value: 373g/mol)

76%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; for 24h;Inert atmosphere; Darkness; Reflux;	N-phenylnaphthalen-1-amine (5.28 g, 24 mmol) , 1-bromo-4-iodobenzene (5.66 g, 20 mmol) , sodium tert-butoxide (2.3 g, 24 mmol) , and palladium (II) acetate (Pd (OAc)2) (225 mg, 1 mmol) were added into a 250 mL two-necked round-bottom flask. The flask was vacuumed and purged with dry nitrogen three times. Then anhydrous toluene (60 mL) and tri-tert-butylphosphine (tBu3P, 1.5 mmol, 1 M toluene solution, 1.5 mL) were added, and the mixture was heated to reflux and stirred for 24 hours in the absence of light. After cooling to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic phase was combined and dried with MgSO4. After removal of the solvent under reduced pressure, the residue was purified by column chromatography on silica gel using dichloromethane/hexane (v/v 1: 5) as the eluent to result in N- (4-bromophenyl) -N-phenylnaphthalen-1-amine as a colorless solid (76%yield) .
64%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 110℃; for 2h;Inert atmosphere;	In a 500 mL two-neck round bottom flaskPhenylnaphthalen-l-amine (50.0 mmol, 11.0 g), 1-bromo-4-iodobenzene (50.0 mmol, 14.1 g)Pd2 (dba) 3 (1.5 mmol, 1.35 g),t-BuONa (100.0 mmol, 9.6 g) was charged and charged with nitrogen. After adding 150 mL of toluene as a solvent and adding P (t-Bu) 3 (1.5 mmol, 0.3 g) and stirring at 110 C for 2 hours, the reaction solution was extracted with dichloromethane . The obtained extract was dried over MgSO4 and dried under reduced pressure to obtain crude product. The crude product was separated and purified by silica gel column chromatography to obtain 12.0 g (yield: 64%) of intermediate 33-1 as a yellow solid.
64%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 110℃; for 2h;Inert atmosphere;	To a 500 mL 2-neck round bottom flask was added N-phenyl naphthalene-1-amine(50.0 mmol, 11.0 g), 1-bromo-4-iodobenzene (50.0 mmol, 14.1 g),Pd2 (dba) 3 (1.5 mmol, 1.35 g) and t-BuONa (100.0 mmol, 9.6 g) were charged and charged with nitrogen.To this was added 150 mL of toluene as a solvent and P (t-Bu) 3 (1.5 mmol, 0.3 g) was added thereto, followed by stirring at 110 C for 2 hours.When the reaction was completed, the temperature of the reaction solution was extracted with dichloromethane to room temperature. The obtained extract was dried over MgSO4 and dried under reduced pressure to obtain crude product. The crude product was separated and purified by silica gel column chromatography to obtain 12.0 g (yield: 64%) of intermediate 33-1 as a yellow solid.
62%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In hexane; toluene; at 85℃;Inert atmosphere;	Compound 4 [Xu, H.; Yin, K.; Huang, W. Chem. Eur. J. 2007, 13(36), 10281-10293] was prepared as follows: a mixture of N-phenylnaphthalen-1-amine (2.767 g, 12.62 mmol), 1-bromo-4-iodobenzene (7.140 g, 25.24 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.578 g, 0.631 mmol), tri-tert-butylphosphine (10 wt. % in hexanes) (5.83 mL, 1.89 mmol), sodium tert-butoxide (NaOtBu) (3.032 g, 31.55 mmol) and anhydrous toluene (80 mL) was degassed with argon for about 40 min while stirring. The reaction mixture was then maintained under argon at about 85 C. while stirring. Upon confirming consumption of the starting material by TLC (SiO2, 100% hexanes), the reaction was cooled to RT and poured over EtOAc (ca. 300 mL). The organics were then washed with sat. NaHCO3, H2O (2×) and brine, dried over MgSO4, filtered and concentrated in vacuo. Purification of the crude product via flash chromatography (SiO2, 8:1-hexanes:CH2Cl2) provided Compound 4 (2.93 g, 62%) as a white foam: confirmed by LCMS (APCI): calculated for C22H16BrN (M+): 374; Found: 374.
45%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 50℃;	Round bottom flask was charged with N-phenylnaphthalen-1-amine 10g, 1-bromo-4-iodobenzene 18.0 g, t-BuONa 6.5 g, Pd2 (dba) 3 1.7 g, (t-Bu) 3P 2.6 ml of toluene 100 ml in and dissolved by stirring in 50 . Check the reaction by TLC and the reaction was terminated after addition of water. The organic layer was extracted with EA, and the residue was filtered under reduced pressure and then purified by column to give the intermediate OP1 7.6 g (yield 45%).
45%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 50℃;	Round bottom flask was charged with Nphenylnaphthalen1amine10 g, 1bromo4iodobenzene18.0 g, tBuONa6.5 g,Pd2 (dba) 31.7 g, (tBu)3P 2.6 ml of toluene 100 ml in and dissolved by stirring to 50 C. Check the reaction by TLC and thereaction was terminated after addition of water. The organic layer was extracted with EA, and the residue was filtered underreduced pressure and then purified by column to give the intermediate OP1 7.6 g (yield 45%).
45%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 50℃;	10 g of N-phenylnaphthalen-1-amine, 18.0 g of 1-bromo-4-iodobenzene, 6.5 g of t-BuONa, 31.7 g of Pd2 (dba)(T-Bu) 3P 2.6 mlWas dissolved in 100 ml of toluene, and the mixture was stirred at 50C .After the reaction was confirmed by TLC, water was added and the reaction was terminated. The organic layer was extracted with EA, filtered under reduced pressure and then subjected to column purification to obtain 7.6 g (yield: 45%) of intermediate OP1-1
8.9 g	With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 6h;Reflux; Inert atmosphere;	To the flask were added 40 mL of xylene, bromoiodobenzene (12. 86 g),(10 g), potassium hydroxide (5. 1 g,), 1,10-phenanthroline (1. 8 g), followed by the addition of cuprous iodide (1: 1). The reaction solution was filtered and the solvent was removed by evaporation under reduced pressure. To the solid precipitate, 50 ml of petroleum ether was added to the precipitate and the mixture was suction-filtered. The mixture was cooled to room temperature,To give color solid 8. 9 g of intermediate 1.

Reference： [1]Tetrahedron,2015,vol. 71,p. 1395 - 1402
[2]Patent: KR2015/140499,2015,A .Location in patent: Paragraph 0385; 0388; 0389
[3]Patent: WO2009/82157,2009,A2 .Location in patent: Page/Page column 27
[4]Patent: WO2018/108070,2018,A1 .Location in patent: Paragraph 213
[5]Chemistry - A European Journal,2007,vol. 13,p. 10281 - 10293
[6]Patent: KR2017/90390,2017,A .Location in patent: Paragraph 0247; 0248-0251
[7]Patent: KR101763838,2017,B1 .Location in patent: Paragraph 0207-0211
[8]Patent: US9112159,2015,B2 .Location in patent: Page/Page column 44
[9]Patent: KR2015/132020,2015,A .Location in patent: Paragraph 0102-0107
[10]Patent: KR2015/132022,2015,A .Location in patent: Paragraph 0064; 0065
[11]Patent: KR2016/21424,2016,A .Location in patent: Paragraph 0073-0078
[12]Journal of Materials Chemistry C,2014,vol. 2,p. 9858 - 9865
[13]Patent: WO2006/73054,2006,A1 .Location in patent: Page/Page column 72-73
[14]Patent: CN103980211,2016,B .Location in patent: Paragraph 0100-0102

34
[ 2039-86-3 ]
[ 90-30-2 ]
[ 906478-51-1 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; for 20h;	Example 5; Synthesis of a monomer of:; [0060] A mixture of phenyl(1-naphthyl)amine (10 g, 45.0 mmol), <strong>[2039-86-3]3-bromostyrene</strong> (9.2 g, 50.0 mmol), NaOfBu (5.1 g, 55.0 mmol), Pd2(dba)3 (0.300 g, 0.33 mmol) and P(fBu)3 (0.150 g, 0.74 mmol) was stirred in toluene (80 ml_) under nitrogen for 20 hours. The resulting solution was diluted with diethylether and filtered through celite and silica. Upon evaporation of the solvent a dark brown viscous material was obtained which was purified by chromatography on silica (hexanes) and the desired product was obtained as a white solid (9.8 g, 67%). The product's 1H NMR is shown below.
67%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; for 20h;Inert atmosphere;	A mixture of phenyl(1-naphthyl)amine (10 g, 45.0 mmol), <strong>[2039-86-3]3-bromostyrene</strong> (9.2 g, 50.0 mmol), NaO'Bu (5.1 g, 55.0 mmol), Pd2(dba)3 (0.300 g, 0.33 mmol) and P('Bu)3 (0.150 g, 0.74 mmol) was stirred in toluene (80 mL) under nitrogen for 20 hours. The resulting solution was diluted with diethylether and filtered through celite and silica. Upon evaporation of the solvent a dark brown viscous material was obtained which was purified by chromatography on silica (hexanes) and the desired product was obtained as a white solid (9.8 g, 67%). See FIG. 2.

Reference： [1]Patent: WO2006/88556,2006,A1 .Location in patent: Page/Page column 18-19
[2]Patent: US7723546,2010,B1 .Location in patent: Page/Page column 12

35
[ 872705-64-1 ]
[ 90-30-2 ]
C₅₆H₄₄N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium t-butanolate;palladium diacetate; tri-tert-butyl phosphine; In toluene; at 100℃;	In a stream of argon, 4.7 g (10 mmol) of Intermediate 5, 5.5 g (25 mmol) of N-phenylnaphthalen-1-amine, 0.03 g (1.5 mol%) of palladium acetate, 0.06 g (3 mol%) of tri-t-butylphosphine, 2.4 g (25 mmol) of t-butoxysodium, and 100 mL of dry toluene were added to a 300-mL three-necked flask provided with a cooling pipe, and then the whole was stirred under heat at 100C overnight. After the completion of the reaction, the precipitated crystal was taken by filtration, and was washed with 50 mL of toluene and 100 mL of methanol, whereby 6.7 g of a pale yellow powder were obtained. The resultant compound was identified as Compound (2) (90% yield) because the measurement of the field desorption mass spectrum (FD-MS) of the compound resulted in m/Z = 744 for C56H44N2 = 744.

Reference： [1]Patent: WO2006/100896,2006,A1 .Location in patent: Page/Page column 29; 30-31
[2]Patent: EP1860097,2007,A1 .Location in patent: Page/Page column 19; 20

36
[ 910893-56-0 ]
[ 90-30-2 ]
C₆₅H₅₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium t-butanolate;palladium diacetate; tri-tert-butyl phosphine; In toluene; at 100℃;	In a stream of argon, 6.0 g (10 mmol) of Intermediate 12, 5.5 g (25 mmol) of N-phenylnaphthalen-1-amine, 0.03 g (1.5 mol%) of palladium acetate, 0.06 g (3 mol%) of tri-t-butylphosphine, 2.4 g (25 mmol) of t-butoxysodium, and 100 mL of dry toluene were added to a 300-mL three-necked flask provided with a cooling pipe, and then the whole was stirred under heat at 100C overnight. After the completion of the reaction, the precipitated crystal was taken by filtration, and was washed with 50 mL of toluene and 100 mL of methanol, whereby 7.3 g of a pale yellow powder were obtained. The resultant compound was identified as Compound (13) (85% yield) because the measurement of FD-MS of the compound resulted in m/Z = 860 for C65H52N2 = 860.

Reference： [1]Patent: WO2006/100896,2006,A1 .Location in patent: Page/Page column 32; 34
[2]Patent: EP1860097,2007,A1 .Location in patent: Page/Page column 21; 23

37
[ 90-30-2 ]
[ 624-83-9 ]
[ 107-66-4 ]
N-methyl-N'-phenyl-N'-α-naphthyl-urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In toluene	7 EXAMPLE 7 EXAMPLE 7 0.5 mole of α-naphthyl-phenylamine was taken together with 0.53 mole of methyl isocyanate and 0.6 g of di-n-butyl phosphate in 150 ml of toluene. The mixture was warmed at 100° C. for 24 hours, with stirring, and then cooled to 10° C. After the product had been filtered off, washed with 150 ml of cold toluene and dried, 0.4 mole of N-methyl-N'-phenyl-N'-α-naphthyl-urea was obtained. Melting point: 146° C./yield: 80% of theory,

Reference： [1]Current Patent Assignee: BAYER AG - US4820871, 1989, A

38
[ 3001-15-8 ]
[ 90-30-2 ]
[ 107-21-1 ]
[ 123847-85-8 ]

Yield	Reaction Conditions	Operation in experiment
55.9%	With copper; potassium carbonate In water; N,N-dimethyl-formamide	5 Synthesis of N,N'-di(1-naphthyl)-N,N'-diphenyl-4,4'-diaminobiphenyl (α-NPD) EXAMPLE 5 Synthesis of N,N'-di(1-naphthyl)-N,N'-diphenyl-4,4'-diaminobiphenyl (α-NPD) To 32.4 g (148 mmol) of N-phenyl-1-naphthylamine were added 25.1 g (61.5 mmol) of 4,4'-diiodobiphenyl, 2.14 g of polyethylene glycol (PEG-6000 (a trade name) manufactured by Wako Junyaku K.K.), 17.1 g (0.124 mol) of potassium carbonate and 15.7 g (247 mmol) of copper (powder) were added, and heated to 200° C. The reaction was traced by high-performance liquid chromatography. Heating was continued under stirring until the peaks of raw materials and intermediates were disappeared (for 12 hours). After the completion of the reaction, water and DMF are added, and the resulting mixture is dispersed, filtrated, and washed with water. The resulting crystal is purified by silica gel chromatography to afford 20.2 g (yield: 55.9%) of N,N'-di(l-naphthyl)-N,N'-diphenyl-4,4'-diaminobiphenyl represented by the formula: The IR analysis is shown in FIG. 5. The 1H-NMR spectrum, 13C-NMR spectrum and FD-MS spectrum are shown in FIGS. 6, 7and 8, respectively.

Reference： [1]Current Patent Assignee: ORIENT CHEMICAL INDUSTRIES CO.,LTD. - US6242648, 2001, B1

39
[ 90-30-2 ]
[ 165550-62-9 ]
[ 937042-81-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 80℃; for 16h;	Step a):A mixture of 0.50 g (0.89 mmol) of N-(2,6-diisopropylphenyl)-9-bromoperylene-3,4-dicarboximide, 0.30 g (1.30 mmol) of <strong>[90-30-2]N-phenyl-1-naphthylamine</strong>, 20 mg (0.018 mmol) of tris(dibenzylideneacetone)dipalladium(0), 90 mg (0.045 mmol) of tris(tert-butyl)phosphine, 130 mg (1.3 mmol) of sodium tert-butoxide and 10 ml of dry toluene was heated to 80 C. under argon and stirred at this temperature for 16 h.After the solvent had been distilled off, the crude product was subjected to column chromatography on silica gel with dichloromethane as the eluent.0.39 g of the amine-substituted perylene was obtained in the form of a violet solid, which corresponds to a yield of 62%.Analytical Data:MS (FD): m/z (rel. int.)=698.2 (100%) [M+].

Reference： [1]Patent: US2008/269482,2008,A1 .Location in patent: Page/Page column 52

40
[ 319906-45-1 ]
[ 90-30-2 ]
[ 302579-20-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate; N,N`-dimethylethylenediamine;copper(l) iodide; In xylene; at 130℃; for 8h;	Under an atmospheric argon gas flow, placing 20.0 g of Intermediate 5, 11.5 g of N-phenyl-1-naphthylamine, 447 mg of copper iodide, 0.532 ml of N,N'-dimethylethylenediamine, 7.22 g of t-butoxy sodium and dehydrated xylene, the reaction was allowed to proceed at 130 C for 8 h. The resultant solution was cooled down and after extracting the reacted solution through 100 ml of toluene it was filtered through sellite, and was condensed. Purifying the resultant crude product by means of a silicagel chromatography (hexane : toluene =9 : 1), the resultant pale yellow solid was washed with methanol, vacuum dried to obtain 16.0 g of white solid, which was analyzed by FD-MS and identified as Intermediate 6.

Reference： [1]Patent: EP2085382,2009,A1 .Location in patent: Page/Page column 39

41
[ 1028647-93-9 ]
[ 90-30-2 ]
[ 1028648-44-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 80℃; for 4h;	Under an atmospheric argon gas flow, blending 4.8 g of N-phenyl-1-naphthylamine, 8.0 g of Intermediate 3, 231 mg of Pd2(dba)3, 325 mg of P(t-Bu)3, 2.9 g of tertialbutoxysodium and toluene, the reaction was allowed to proceed at 80 C for 4 h. The resultant solution was cooled down and after adding toluene, it was filtered through sellite and was condensed. Purifying the resultant mixture by means of a silicagel chromatography (hexane : dichloromethane =6 : 1), the resultant solid was washed with n-hexane, vacuum dried to obtain 8.96 g of yellowish white solid, which was analyzed by FD-MS and identified as Compound H4.

Reference： [1]Patent: EP2085382,2009,A1 .Location in patent: Page/Page column 42

42
[ 90-30-2 ]
[ 17533-36-7 ]
[ 403671-76-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With tri-tert-butyl phosphine; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In toluene; for 12h;Heating;	5g of dibromo-tetrahydropyrene (leq, 0.0137mol) obtained in Preparation Example 1-2 and 6.6g of N-phenylnaphthalene-1-amine (2.2eq, 0.03mol) were dissolved in 200ml of toluene in a flask. 0.37g of Pd2(dba)3 (0.03eq, 0.4mol), 3.8g of Na(t-Bu)O (2.2eq, 0.03mol), and 0. Ig of P(t-Bu)3 (O.Obetaeq, 0.8mmol) were added to the mixture solution respectively, and then the resultant mixture solution was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through celite, and then 6.6g of aryl amine derivative represented by Formula 1-1 (HT-2) was obtained from the filtrate through column chromatography (yield 76%) . <n="26"/>Tg: 1840C1H-NMR: 7.61 (t, IH), 7.48 (t, IH), 7.44 (t, IH), 7.16(m, 2H), 7.01(t, 2H), beta.55(t, IH), 6.2(t, IH), 2.98(d, 2H).

Reference： [1]Patent: WO2009/82157,2009,A2 .Location in patent: Page/Page column 24-25

43
[ 106-37-6 ]
[ 90-30-2 ]
[ 138310-84-6 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 4726 - 4734
[2]Polymer,2012,vol. 53,p. 1849 - 1856

44
[ 90-30-2 ]
[ 98057-08-0 ]
[ 1172120-72-7 ]

Yield	Reaction Conditions	Operation in experiment
47%	With 1,1'-bis(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In toluene at 90℃; for 15h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Chang, Yuan Jay; Chow, Tahsin J. [Tetrahedron, 2009, vol. 65, # 24, p. 4726 - 4734]

45
[ 18052-76-1 ]
[ 62-53-3 ]
[ 90-30-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 869 - 873

46
[ 19549-87-2 ]
[ 90-30-2 ]
[ 122-39-4 ]
[ 98-83-9 ]
4-nonyldiphenylamine [ No CAS ]
4-α-methylstyryl-4'-nonyldiphenylamine [ No CAS ]
4,4'-dinonyldiphenylamine [ No CAS ]
[ 10081-67-1 ]
4-(α,α-dimethylbenzyl)diphenylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The reaction is carried out in a 1000 ml glass reaction vessel equipped with No. Jacket filled with a heatable high temperature oil No. Reflux cooler equipped with a water separator, which is filled with tripropylene be- fore start-up No. Feed unit for tripropylene and a-methyl-styrene reactants No. Propeller stirrer No. Temperature indicator No. Sampling device. The reaction vessel is loaded with 113.4 diphenylamine (DUSLO) and 146.9 g phenyl- a-naphthylamine (Merck). 26.0 g FULCAT 22B (Rockwood Additives) are added under stirring. The reaction vessel is sealed, evacuated to 20 mbar and relieved with nitrogen for inert conditions. The stirrer speed is set to 500 rpm, and the reaction vessel is heated to 220C within 1 hour. At this temperature 423 g tripropylene (Exxon Europe) is fed to the reaction vessel during 2 h. The reaction mixture begins to boil after 10 min from the start of the tripropylene feed. The water adsorbed on the catalyst is distilled off as,an azeotrope with tripropylene and removed in a water separator.. Due to the con- stantly added tripropylene, the boiling point of the reaction mass is reduced gradually from 220 to 160-165C by the end of the feed. The reaction mixture is kept boiling during the complete feed time by adjusting the jacket temperature 20C higher than the temperature of the reaction mixture. By stirring for an additional 4 h at 160-165C the diphenylamine content in the reaction mass is reduced below 10% in respect to the amine content. The reaction mixture is cooled to 130C within 0.5 h. 79 g of a-methyl- styrene (Merck) is added at 130C within 1 h. During the course of the reaction the temperature of the reaction mixture is increased to 133-134C. The final content of <1% diphenylamine in respect to the amine content in reaction mass is obtained during an additional reaction time of 2 h. 3.2 Analytical Results 3.2.1 Capillary column gas chromatography; 3.2.2 Elemental analysis according to DUMAS method: 87.0% carbon, 9.8% hydrogen, 3.6% nitrogen 3.2.3 Basic nitrogen determined by perchloric acid titration: 3.5% 3.2.4 Kinematic viscosity at 80C, 58 mm2/s

Reference： [1]Patent: WO2005/97728,2005,A1 .Location in patent: Page/Page column 32-33

47
[ 1158651-12-7 ]
[ 90-30-2 ]
[ 1268840-08-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; In toluene; at 90℃; for 3h;	4.38 g (20 mmol) of naphthalene-2-phenylamine, 12.3 g (30 mmol) of Intermediate 6, 2.88 g (30 mmol) of t-BuONa, 0.36 g (0.4 mmol) of Pd2(dba)3, and 0.08 g (0.4 mmol) of P(t-Bu)3 were dissolved in 100 mL of toluene and then the mixture was stirred for 3 hours at a temperature of 90C. When the reaction was completed, the reaction solution was cooled to room temperature and then extracted three times with distilled water and 100 mL of diethylether, thereby obtaining an organic layer. The organic layer was dried over magnesium sulfate and the residue obtained by evaporating the solvent was isolated and purified by silica gel column chromatography to obtain 8.8 g (yield 88%) of Intermediate 8. The obtained compound was identified by HR-MS. C32H22BrN calc.: 499.0936; found 499.0940

Reference： [1]Patent: EP2298741,2011,A1 .Location in patent: Page/Page column 28

48
[ 90-30-2 ]
[ 1371570-95-4 ]
[ 1371570-26-1 ]

Yield	Reaction Conditions	Operation in experiment
35%	With sodium t-butanolate;tri-tert-butyl phosphine; palladium diacetate; In toluene; at 100℃; for 18h;Inert atmosphere;	c) 0.42 g (4.35 mmol) sodium tert-butoxide are added to 1.00 g (1.89 mmol) of the product of example 4b in 15 ml toluene. 0.91 g (4.16 mmol) N-phenyl-N-naphthylamine are added. The reaction mixture is degassed with argon. 21 mg (0.09 mmol) palladium(II) acetate are added. 38 mg (0.19 mmol) tri-tert-butylphosphine are added. The reaction mixture is stirred for 18 h at 100 C. under argon. The reaction mixture is filtered through a plug of silica gel, and the solvent of the filtrate is distilled off. Column chromatography on silica gel with toluene cyclohexane 1/4 results in the product (B-2) (yield: 540 mg (35%))1H NMR (360 MHz, THF-d8, delta): 8.58 (d, J=9.0 Hz, 1H), 7.84-7.94 (m, 4H), 7.73-7.82 (m, 4H), 6.88-7.57 (m, 31H).
35%	With tri-tert-butyl phosphine; sodium t-butanolate;palladium diacetate; In toluene; at 100℃; for 18h;Inert atmosphere;	0.42 g (4.35 mmol) sodium tert-butoxide are added to 1.00 g (1.89 mmol) of the product of example 4b in 15 ml toluene. 0.91 g (4.16 mmol) N-phenyl-N-naphthylamine are added. The reaction mixture is degassed with argon. 21 mg (0.09 mmol) palladium(ll) acetate are added. 38 mg (0.19 mmol) tri-tert-butylphosphine are added. The reaction mixture is stirred for 18 h at 100 C under argon. The reaction mixture is filtered through a plug of silica gel, and the solvent of the filtrate is distilled off. Column chromatography on silica gel with toluene cyclohexane 1/4 results in the product (B-2) (yield: 540 mg (35 %))1 H NMR (360 MHz, THF-d8, delta): 8.58 (d, J = 9.0 Hz, 1 H), 7.84-7.94 (m, 4H), 7.73-7.82 (m, 4H), 6.88-7.57 (m, 31 H).

Reference： [1]Patent: US2012/95222,2012,A1 .Location in patent: Page/Page column 35
[2]Patent: WO2012/45710,2012,A1 .Location in patent: Page/Page column 44

49
[ 1144-13-4 ]
anilinomagnesium bromide [ No CAS ]
[ 90-30-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With bis(1,5-cyclooctadiene)nickel (0); 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene; In tetrahydrofuran; 1,4-dioxane; at 150℃; for 24h;Inert atmosphere;	General procedure: The synthetic procedure of (2-naphthyl)diphenylamine (g) is used as an example hereinafter. 2-Naphthyl N,N-dimethylsulfamate (76 mg, 0.30 mmol), Ni(cod)2 (7.8 mg, 0.030 mmol), and 1,4-dioxane solution of IPr (23.5 mM, 2.6 mL) were charged in a two-neck flask in Ar atmosphere. To the resulting mixture, THF solution of bromomagnesium diphenylamide (1.0 M, 0.6 mL) was added dropwise. After stirring for 24 h at 110 C, the product was isolated using silica gel chromatography.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 5531 - 5534

50
[ 90-30-2 ]
C₃₀H₁₇Br₂NS [ No CAS ]
[ 1350841-95-0 ]

Yield	Reaction Conditions	Operation in experiment
68%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 110℃; for 24h;	The intermediate M obtained from the above step, N-phenylnaphthalene-1-amine, Pd2(dba)3, P(tBu)3, and NaOtBu were dissolved in a toluene solvent, followed by reflux for 24 hours at 110 C. Upon completion of the reaction, the reaction product was subjected to vacuum filtration through Celite and silica gel by using a hot toluene solvent. The temperature of the filtrate was cooled to room temperature, and then the precipitated product was recrystallized again using toluene and acetone, with the result that desired compound 6-3 was obtained by a yield of 68%.
68%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 110℃; for 24h;	After the dissolved intermediate obtained in step M and N-phenylnaphthalen-1-amine, Pd2 (dba) 3, P (tBu) 3 and NaOtBu in toluene solvent, and refluxed for 24 hours at 110C . The reaction using hot toluene solvent and the reaction terminated when the cellThe residue was filtered under reduced pressure was purified by silica gel by using a light with. After cooling to room temperature, and then the precipitated product was re-crystallized using toluene and acetone to give the desired compound 6-3 again screen in 68% yield.

Reference： [1]Patent: US2013/69049,2013,A1 .Location in patent: Paragraph 0101; 0105-0106
[2]Patent: KR101604642,2016,B1 .Location in patent: Paragraph 0130-0133; 0136-0137

51
[ 5419-55-6 ]
[ 589-87-7 ]
[ 90-30-2 ]
[ 717888-41-0 ]

Yield	Reaction Conditions	Operation in experiment
7.5 g	Stage #1: 1,4-bromoiodobenzene; N-phenyl-1-naphthylamine With copper(l) iodide; sodium t-butanolate; N,N`-dimethylethylenediamine In toluene at 110℃; for 8h; Inert atmosphere; Stage #2: With n-butyllithium In 5,5-dimethyl-1,3-cyclohexadiene; hexane at -30℃; for 1h; Inert atmosphere; Stage #3: Triisopropyl borate Further stages;	Synthesis Example 7 (Synthesis of Intermediate 7) General procedure: 11.1g of N-phenyl-1-naphthylamine, 15.6g of 4-iodobromobenzene, 1.9g of copper(I)iodide, 2.0g of N,N'-dimethylethylenediamine, 8.6g of sodium tert-butoxide and 100 mL of dehydrated toluene were placed in a 300 mL three-necked flask under a flow of argon. The mixture was stirred at 110°C for 8 hours. After the reaction was completed, the resultant was extracted with toluene and then dried with magnesium sulfate. The extract was condensed under reduced pressure, and the crude product obtained was purified using column chromatography. The purified substance was recrystallized with toluene, filtered out and dried to obtain 16.8g of white powder. 16.8g of the above-mentioned white powder and 100 mL of dehydrated xylene were placed in a 300 mL three-necked flask under a flow of argon, and cooled to -30°C. 30 mL of n-butyllithium (1.6M hexane solution) was added thereto and reacted for an hour. After cooled to -70°C, 28 mL of triisopropyl borate was added. After heated slowly, the mixture was stirred at room temperature for an hour. 32 mL of 10% hydrochloric acid solution was added and stirred. The mixture was extracted with ethyl acetate and water, and the organic layer was washed with water. The resultant was dried with anhydrous sodium sulfate and the solvent was distilled away. The resultant was washed with hexane to obtain 7.5g of white powder.

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP2589596, 2013, A1 Location in patent: Paragraph 0103; 0104

52
[ 13922-41-3 ]
[ 62-53-3 ]
[ 90-30-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; In water; at 20℃;	General procedure: In a typical example, phenylboronic acid 1 (1.22 g, 1 mmol) was charged in the flask containing K2CO3 (2 equiv) in water as solvent (2 mL). To this was added aniline 2 (0.93 g, 1 mmol) and Cu-Mn catalyst, and the reaction mixture was allowed to stir at room temperature. The completion of the reaction was monitored by TLC. After completion, the base was neutralized using 2 N HCl and the catalyst was filtered off, thorough washings of water were given, extracted with ethyl acetate, and the organic layer was separated and dried under reduced vacuum. The crude product obtained was purified on silica gel column chromatography (solvents, ratio?), to obtain white crystalline product diphenylamine 3a (1.60 g) with 95% yield. All reactions were similarly carried out.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 5351 - 5354
[2]New Journal of Chemistry,2019,vol. 43,p. 2861 - 2864

53
[ 134-32-7 ]
[ 98-80-6 ]
[ 90-30-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate; In water; at 20℃; for 5h;	General procedure: To a stirred solution of phenylboronic acid (1.0 mmol), aniline (1.0 mmol), and K2CO3 (2.0 mmol) in deionized H2O (10 mL) at room temperature was added an aqueous suspension of FePd nanowires (3.0 mol % in 3 mL of H2O). The mixture was stirred at room temperature for 5h. After completion of the reaction (as monitored by TLC), 2 M HCl was added and the catalyst was separated by applying an external magnet. The catalyst was washed with EtOAc. The mixture was extracted with EtOAc (2 * 20 mL), dried, and concentrated. The residue was subjected to gel permeation chromatography to afford pure product.
75%Spectr.	With L-arginine; palladium dichloride; In ethanol; water; at 25℃; for 3h;Green chemistry;	General procedure: Amine (1.0 mmol), phenylboronic acid (1.1 mmol), L-arginine (1 mmol) and PdCl2 (1 mol%) were taken in a 25 ml single neckround-bottomed flask to which 3 ml of water/EtOH (1:1) wasadded. The reaction mixture was stirred for appropriate time at room temperature (Table 2). The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was washed with EtOAc (215 ml) and the organic phase separated, dried over anhydrous Na2SO4 and evaporated under reduced pressure. The crude material was purified by column chromatography over silica gel to afford the corresponding product in high purity.
98%Chromat.	With C32H32Cl2Cu2N4O4; triethylamine; In ethanol; for 5h;	General procedure: In a typical run, an oven-dried 10 ml round bottom flask was charged with a known mole percent of catalyst and base, phenylboronic acid (1.2 mmol) and aniline (1.0 mmol) with ethanol (5 ml). The mixture was stirred at ambient temp (25 C). After the specified time (5 h)stirring was stopped, water (20 ml) was added, and extraction with ether (2×10 ml) was done. The combined ether extract was washed with water (3×10 ml), dried over anhydrous Na2SO4, and filtered. Solvent was removed under vacuum. The residue was dissolved in hexane and analyzed by GC-MS.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 2813 - 2817
[2]RSC Advances,2017,vol. 7,p. 46022 - 46027
[3]Applied Organometallic Chemistry,2018,vol. 32
[4]RSC Advances,2014,vol. 4,p. 22775 - 22778
[5]Tetrahedron Letters,2017,vol. 58,p. 3482 - 3486
[6]Inorganica Chimica Acta,2020,vol. 500
[7]ChemCatChem,2020,vol. 12,p. 3010 - 3021

54
[ 90-30-2 ]
[ 717888-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: copper(l) iodide; N,N`-dimethylethylenediamine; sodium t-butanolate / toluene / 8 h / 110 °C / Inert atmosphere 2.1: n-butyllithium / hexane; 5,5-dimethyl-1,3-cyclohexadiene / 1 h / -30 °C / Inert atmosphere 2.2: 1 h / -70 - 20 °C
	Multi-step reaction with 2 steps 1.1: copper(l) iodide; potassium hydroxide; phenanthroline monohydrate / o-xylene / 15 h / 220 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C
	Multi-step reaction with 2 steps 1.1: potassium hydroxide; 1,10-Phenanthroline; copper(l) iodide / 5,5-dimethyl-1,3-cyclohexadiene / 6 h / Reflux; Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 2.2: Neutral conditions

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP2762478, 2014, A1
[2]Zheng, Zhiwen; Dong, Qingchen; Gou, Liao; Su, Jian-Hua; Huang, Jinhai [Journal of Materials Chemistry C, 2014, vol. 2, # 46, p. 9858 - 9865]
[3]Current Patent Assignee: SHANGHAI TAOE CHEMICAL TECHNOLOGY CO LTD - CN103980211, 2016, B

55
[ 589-87-7 ]
[ 90-30-2 ]
N-(4-bromophenyl)-1-naphthylphenylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With copper(l) iodide; sodium t-butanolate; N,N`-dimethylethylenediamine; In toluene; at 110℃; for 8h;Inert atmosphere;	[0189] In an argon atmosphere, 21.9 g (100.0 mmol) of <strong>[90-30-2]N-phenyl-1-naphthylamine</strong>, 31.1 g (110.0 mmol) of 4-iodobromobenzene,3.8 g (20.0 mmol) of copper iodide (I), 4.0 g (45.0 mmol) of N,N?-dimethylethylenediamine, and 19.2 g(200.0 mmol) of sodium t-butoxide were added with 200 ml of dehydrated toluene. The resultant mixture was allowedto react at 110 C for 8 h. After the reaction, the reaction mixture was extracted with toluene, and the organic layer wasdried over MgSO4 and then concentrated. The concentrate was purified by silica gel column chromatography. The crudeproduct was recrystallized from toluene, collected by filtration, and dried to obtain 33.6 g of white solid, which wasidentified as N-(4-bromophenyl)-1-naphthylphenylamine by FD-MS (yield: 90%).

Reference： [1]Patent: EP2762478,2014,A1 .Location in patent: Paragraph 0189

56
[ 90-30-2 ]
[ 201731-79-5 ]
C₄₂H₂₉N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 16h; Inert atmosphere; Schlenk technique;

Reference： [1]Wu, Cheng-Lung; Chang, Che-Hong; Chang, Yung-Ting; Chen, Chin-Ti; Chen, Chao-Tsen; Su, Chi-Jung [Journal of Materials Chemistry C, 2014, vol. 2, # 35, p. 7188 - 7200]

57
[ 90-30-2 ]
C₁₆H₂⁽²⁾H₁₁N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With 10% Pt/activated carbon; palladium 10% on activated carbon; hydrogen; water-d2; at 80℃; for 4h;	General procedure: The relevant protonated arylamine (1-12 g) was suspended in D2O (~25 mL per gram of arylamine) in a two-neck round bottom flask, to which Pt/C (10% w/w, ~1 mol %) and Pd/C (10% w/w,~1.5 mol %) were added. The flask was sealed, and the stirring reaction mixture was purged with one balloon of N2(g), followed by one balloon of H2(g), ensuring that the flask was not pressurised. The reaction mixture was heated at 80 C for 4 h in the case of 1, 2 and 4, and 24 h in the case of 3. The reaction mixture was allowed to cool, CH2Cl2 (~25 mL) was added to the reaction flask, and the mixture filtered over Celite to remove the catalyst, which was then washed with CH2Cl2 (50-100 mL).The filtrate was extracted with 3 × 50 mL CH2Cl2, the combined organics dried over Na2SO4, filtered and evaporated to dryness to yield the deuterated product.

Reference： [1]Molecules,2014,vol. 19,p. 18604 - 18617

58
[ 589-87-7 ]
[ 90-30-2 ]
N1,N4-di(naphthalen-1-yl)-N1,N4-diphenylbenzene-1,4-diamine [ No CAS ]
[ 138310-84-6 ]

Yield	Reaction Conditions	Operation in experiment
6%Chromat.; 94%Chromat.	With copper(l) iodide; sodium t-butanolate; In tetrahydrofuran; at 100℃; for 12h;Inert atmosphere;Catalytic behavior;	A solution of CuI (6.7 mg, 0.035 mmol), NaOtBu (85 mg, 0.88 mmol), 1-bromo-4-iodobenzene (1a) (100 mg, 0.35 mmol), and N,N-diphenylamine (2a) (90 mg, 0.53 mmol) in THF (0.5 mL) was stirred at 60 C for 12 h. The reaction was quenched with H2O, and extracted with CH2Cl2 (3*4 mL). ;The chemoselectivity (3aa/4aa≥98/2) was measured by HPLC analysis using Inertsil ODS-3V. The pure monoaminated product 3aa (113 mg, 98%) was obtained by flash chromatography (hexane/CH2Cl2=97/3) as a white solid.

Reference： [1]Tetrahedron,2015,vol. 71,p. 1395 - 1402

59
[ 591-18-4 ]
[ 90-30-2 ]
[ 1224893-33-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate; In toluene; at 100℃; for 12h;Inert atmosphere;	General procedure: General procedure for the palladium-catalyzed reaction A solution of Pd(OAc)2 (0.8 mg, 0.0036 mmol), Xantphos (2.1 mg, 0.0036 mmol), NaOtBu (51 mg, 0.53 mmol), 1-bromo-4-iodobenzene (1a) (100 mg, 0.35 mmol), and N,N-diphenylamine (2a) (72 mg, 0.43 mmol) in toluene (0.5 mL) was stirred at 100 C for 12 h. The reaction was quenched with H2O, and extracted with CH2Cl2 (3*3 mL). The chemoselectivity (3aa/4aa=92/8) was measured by HPLC analysis using Inertsil ODS-3V. The pure monoaminated product 3aa (99 mg, 86%) was obtained by flash chromatography (hexane/CH2Cl2=97/3) as a white solid.

Reference： [1]Tetrahedron,2015,vol. 71,p. 1395 - 1402

60
[ 90-30-2 ]
[ 528610-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine / toluene; hexane / 85 °C / Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / 100 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine / toluene / 50 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / Reflux
	Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate / toluene / 50 °C 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / toluene / Reflux

Multi-step reaction with 2 steps 1: sodium t-butanolate; palladium diacetate; tri-tert-butyl phosphine / toluene / 24 h / Inert atmosphere; Darkness; Reflux 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 24 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: NITTO DENKO CORPORATION - US9112159, 2015, B2
[2]Current Patent Assignee: DONGJIN SEMICHEM CO.,LTD. - KR2015/132022, 2015, A
[3]Current Patent Assignee: DONGJIN SEMICHEM CO.,LTD. - KR2016/21424, 2016, A
[4]Current Patent Assignee: HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY - WO2018/108070, 2018, A1

61
[ 62-53-3 ]
[ 104190-22-9 ]
[ 90-30-2 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 1696 - 1703

62
[ 90-30-2 ]
C₃₆H₂₂ClNO [ No CAS ]
C₆₄H₄₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 80℃; for 2h;	The 958mg (1.54mmol) of intermediate B-11 (8), 373mg (1.7mmol) of N- phenyl-naphthalene-1-amine, 183mg (0.2mmol) of tris (dibenzylideneacetone) dipalladium (0 ), 40mg (0.2mmol) of tri (tert-butyl) phosphine and 336mg (3.5mmol) of sodium tert-butoxide was added 20mL of toluene, and then, at the temperature 80 the mixed solution was stirred for 2 hours. The organic layer was dried using magnesium sulfate to derive therefrom the solvent is removed, and then, using a silica gel column chromatography and the residue was purified to obtain 882mg (0.94mmol, yield: 67%) of compound 174A. Compound MS / FAB and 1HNMR identified synthetic.

Reference： [1]Patent: CN105481829,2016,A .Location in patent: Paragraph 0690; 0691

63
[ 90-30-2 ]
C₄₂H₂₆ClNS [ No CAS ]
C₅₈H₃₈N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 80℃; for 2h;	The 1.01g (1.65mmol) of Intermediate A-10 (9), 392mg (1.8mmol) of N- phenyl-naphthalene-1-amine, 183mg (0.20mmol) of tris (dibenzylideneacetone) dipalladium ( 0), 40mg (0.20mmol) of tri (tert-butyl) phosphine and 384mg (4.0mmol) of sodium tert-butoxide was added 20mL of toluene, and then, at the temperature 80 the mixed solution was stirred for 2 hours. After the reaction solution was cooled to room temperature, water and diethyl ether and the organic layer was extracted twice therefrom. The organic layer was dried using magnesium sulfate to remove the solvent therefrom, and then, using a silica gel column chromatography and the residue was purified to obtain 1.15g (1.45mmol, yield: 88%) of compound 185. FAB MS using a compound identified synthetic.

Reference： [1]Patent: CN105481829,2016,A .Location in patent: Paragraph 0573; 0574

64
[ 352359-42-3 ]
[ 90-30-2 ]
4,4'-bis[N-(1-naphthyl)-N-phenylamino] biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In toluene; at 100℃; for 24h;	N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine (10.8g, 24mmol) was dissolved in toluene, N-phenylnaphthalen-1-amine (4.4 g, 20mmol), Pd2(dba)3 (0.05 equiv), PPh3 (0.1 equiv.), were added to each of NaOt-Bu (3 eq.), stirred and refluxed for 24 hours at 100 C. After the reaction was terminated and the resulting organic material was extracted and the organic layer was dried over MgSO4 and concentrated in ether and water silicagel column and the final compound was recrystallized 11.4g (yield: 81%) was obtained.
81%	With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In toluene; at 100℃; for 24h;	N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine (10.8g, 24mmol) was dissolved in toluene, N-phenylnaphthalen-1-amine (4.4g,20mmol), Pd2 (dba) 3 (0.05 eq.), PPh3 (0.1 eq.) and NaOt-Bu (3 eq.) were added, stirred at 100 degree C and refluxed for 24 hours. After completion of the reaction, the organic layer was extracted with water and ether, and the resulting compound was purified by silica gel column, then concentrated, dried over MgSO4 and recrystallized to give the final compound 11.4g (yield: 81%).
81%	With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In toluene; at 100℃; for 24h;	N-(4?-bromo-[1,1?-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine (10.8 g, 24 mmol) was dissolved in toluene and, N-phenylnaphthalen-1-amine (4.4 g, 20 mmol), Pd2(dba)3 (0.05 eq.), PPh3 (0.1 eq.), NaOt-Bu (3 eq.) were added and refluxed with stirring at 100 C. for 24 hours. When the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO4 and concentrated. The resulting compound was separated by silicagel column chromatography and recrystallized to obtain 11.4 g (yield: 81%) of the product.

Reference： [1]Patent: KR2015/31892,2015,A .Location in patent: Paragraph 0293-0295
[2]Patent: KR101614738,2016,B1 .Location in patent: Paragraph 0405-0407
[3]Patent: US2019/241548,2019,A1 .Location in patent: Paragraph 0125; 0167-0168

65
[ 90-30-2 ]
[ 105946-82-5 ]
[ 352359-42-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	With copper; potassium carbonate; sodium sulfate; In nitrobenzene;	The starting material, N-phenylnaphthalen-1-amine (65.8g, 300mmol) in 4-bromo-4'-iodo-1,1'-biphenyl (129.2g, 360mmol), Na2SO4 (42.6g, 300mmol), K2CO3 (41.4 g, 300mmol), Cu (5.72g, 90mmol), to the use of the nitrobenzene product synthesis example 89.2g (yield 66% was obtained).
66%	With copper; potassium carbonate; sodium sulfate; In nitrobenzene; at 200℃;	Starting material, N-phenylnaphthalen-1-amine (65.8 g, 300 mmol), 4-bromo-4'-iodo-1,1'-biphenyl (129.2 g, 360mmol), Na2SO4 (42.6 g, 300 mmol), K2CO3 (41.4 g, 300 mmol), Cu (5.72 g, 90 mmol), nitrobenzene was obtained using the synthesis method of Sub 1-1 of Example 2 above to obtain 89.2 g of product (yield: 66%).

Reference： [1]Patent: KR2015/31892,2015,A .Location in patent: Paragraph 0188-0190
[2]Patent: KR102098061,2020,B1 .Location in patent: Paragraph 0321; 0327-0330

66
[ 589-87-7 ]
[ 90-30-2 ]
[ 528610-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate / toluene / 50 °C 2: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate / toluene

Reference： [1]Current Patent Assignee: DONGJIN SEMICHEM CO.,LTD. - KR2015/132020, 2015, A

67
[ 90-30-2 ]
5,9-dibromo-7,7-dimethyl-7H-benzo[c]fluorene [ No CAS ]
C₅₁H₃₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With bis(tri-t-butylphosphine)palladium(0); sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; at 120℃; for 4h;	dibromobenzothiofluorene (10 g, 24.86 mmol) and <strong>[90-30-2]N-phenyl-1-naphthylamine</strong> (10.9 g, 49.7 mmol), NaOtBu (9.53 g, 99.46 mmol) and xylene (100 ml) were mixed and heated to 120 C. Pd (p-t-Bu3) 2 (762 mg, 1.49 mmol) was added thereto and refluxed for 4 hours. After cooling to room temperature, purification was carried out by column chromatography. After drying, structural formula 2 (15 g, yield 88%) was obtained.

Reference： [1]Patent: KR101638665,2016,B1 .Location in patent: Paragraph 0075-0077

68
9-(3,5-dibromophenyl)-9H-carbazole [ No CAS ]
[ 90-30-2 ]
C₅₀H₃₅N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In o-xylene; at 130℃; for 3h;Inert atmosphere;	A 250 mE 3-neck round bottom flask was charged with nitrogen, and then a compound A which is 9-(3,5-dibro- mophenyl)-9H-carbazole (24.9 mmol, 10.0 g), a compound M which is N-phenyl-1 -naphthylamine (49.9 mmol, 10.9 g), palladium acetate (Pd(OAc)2 1.2 mmol, 0.3 g), sodium tert-butoxide (50.0 mmol, 4.8 g), 100 mE of o-xylene, and tri-tert-butylphosphine (2.4 mmol, 0.6 mE) were added thereto, and the resulting mixture was heated at 130 C. for 3 hours. The solution of the mixture was cooled to room temperature, stirred in 500 mE of methanol for 20 minutes, and filtered, thereby obtaining 15.0 g of a solid, Compound 4 (yield: 88%).MAEDI-TOF: m/z677.2076 (C50H35N3677.83)1H-NMR (CDC13, 500 MHz) oe: 7.96-8.06 (m, 6H), 7.84 (d, J7.80 Hz, 2H), 7.59 (t, J8.16 Hz, 4H), 7.51 (t, J7.73 Hz, 2H), 7.41 (d, J7.72 Hz, 2H), 7.10-7.25 (m, 12H), 6.88-6.96 (m, 4H), 6.65 (s, 1H), 6.17 (d, J1.85 Hz, 2H)

Reference： [1]Patent: US9680107,2017,B2 .Location in patent: Page/Page column 21

69
[ 90-30-2 ]
9-(3,5-dibromophenyl)-3,6-diphenyl-9H-carbazole [ No CAS ]
C₆₂H₄₃N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In o-xylene; at 130℃; for 4h;Inert atmosphere;	A 250 mE 3-neck round bottom flask was charged with nitrogen, and then a compound B which is 9-(3,5-dibro- mophenyl)-3,6-diphenyl-9H-carbazole (9.1 mmol, 5.0 g), a compound L which is (4-anilinophenyl)diphenylamine (20.0mmol, 6.7 g), palladium acetate (Pd(OAc)2 0.9 mmol, 0.2 g), sodium tert-butoxide (20.0 mmol, 1.9 g), 100 mE of o-xylene, and tri-tert-butylphosphine (1.8 mmol, 0.4 mE) were added thereto, and the resulting mixture was heated at 130 C. for 4 hours. The solution of the mixture was cooled to room temperature, and 100 mE of tetrahydrofuran wasadded thereto. The mixture solution was stirred in 800 mE of methanol for 25 minutes, and filtered, thereby obtaining 10.0 g of a white solid, Compound 8 (yield: 103%).MAEDI-TOF: mlz=1063.61 52 (C78H57N5=1 064.32)1H-NMR (DMSO, 500 MHz) oe: 8.68 (s, 2H), 7.9 (d, J=7.5 Hz, 4H), 7.70 (d, J=8 Hz, 2H), 7.51 (t, J=8 Hz, 6H),7.38-7.34 (m, 6H), 7.22 (t, J=7 Hz, 12H), 7.17 (d, J=8 Hz,4H), 7.06 (t, J=6 Hz, 2H), 6.99-6.95 (m, 16H), 6.64 (s, 1H),6.58 (s, 2H)

Reference： [1]Patent: US9680107,2017,B2 .Location in patent: Page/Page column 26; 27

70
[ 90-30-2 ]
9-(3,5-dibromophenyl)-3,6-bis(9,9-dimethyl-9H-fluoren-2-yl)-9H-carbazole [ No CAS ]
C₈₀H₅₉N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In o-xylene; at 130℃; for 5h;Inert atmosphere;	An 100 mE 3-neck round bottom flask was charged with nitrogen, and then a compound C which is 9-(3,5-dibro-mophenyl)-3,6-bis(9,9-dimethyl-9H-fluoren-2-yl)-9H-car- bazole (13.4 mmol, 10.5 g), a compound M which is <strong>[90-30-2]N-phenyl-1-naphthylamine</strong> (29.4 mmol, 5.0 g), palladium acetate (Pd(OAc)2 1.3 mmol, 0.3 g), sodium tert-butoxide (29.4 mmol, 2.8 g), 60 mE of o-xylene, and tri-tert-butyl-phosphine (2.7 mmol, 0.6 mE) were added thereto, and the resulting mixture was heated at 130 C. for 5 hours. The solution of the mixture was cooled to room temperature, stirred in 240 mE of methanol for 30 minutes, and filtered, thereby obtaining 12.1 g of a solid, Compound 11 (yield:85%).MAEDI-TOF: m/z106 1.7176 (C80H59N31 062.34)

Reference： [1]Patent: US9680107,2017,B2 .Location in patent: Page/Page column 28; 29

71
1,7-dibromopyrene [ No CAS ]
[ 90-30-2 ]
N₁,N₇-bis(naphthalen-1-yl)-N₁,N₇-diphenylpyrene-1,7-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.2%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 50 - 110℃; for 18h;	A 1,7-dibromo pyrene (5.5g, 15.2mmol) and N- phenyl-1-naphthalene-amine (7.36g, 33.6mmol), sodium -t- butoxide (3.67g, 38.2mmol) dissolved in dry toluene (50wt% in toluene, 4.6g, 22.91mmol) and Pd2 (dba) 3 (2.8g, 3.0mmol) were added slowly at 50 C and the reaction was allowed to proceed to 110 C .After 18 hours, the reaction was terminated by adding excess water and the organic material was extracted with dichloromethane (2 x 70 ml). The organic layer was dried over MgSO4 and purified by column chromatography (n-hexane: ethylacetate, 5: 1)Yellow SolidN1, N7-di (naphthalen-1-yl) -N1, N7-diphenylpyrene-1,7-diamine (Compound 1) (6.7 g, 69.2%).
700 mg	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; for 3.25h;Inert atmosphere; Reflux;	c. Compound 2 10334] To 2.1 g of Intermediate 2 in 100 mL toluene under nitrogen atmosphere was added 36 mg of P(t-13u)3 and 323 mg of Pd2(dba)3. Next, 2.17 g of N-phenyl- 1 -naphthylamine and 951 mg of sodium tert-butoxide were added. The reaction was heated at reflux for 3.25 hours, cooled to room temperature and filtered through a plug of Celite. Water was added to the filtrate and the mixture was extracted with dichioromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated by rotary evaporation to give a dark amber oil. The crude material was dissolved in 5:3 hexanes:dichioromethane and purified by MPLC on silica gel eluting with 90:10 to 65:35 hexanes:dichioromethane. The purest fractions (analyzed by UPLC) were combined and concentrated by rotary evaporation to provide Compound 2 (700 mg, 99.74% pure) as a yellow solid. Final purification prior to device preparation was accomplished by vacuum sublimation.

Reference： [1]Patent: KR2018/105918,2018,A .Location in patent: Paragraph 0100; 0109-0111
[2]Patent: US2017/29362,2017,A1 .Location in patent: Paragraph 0331; 0334

72
[ 1005771-04-9 ]
[ 90-30-2 ]
7-tert-butyl-N1,N3-bis(phenyl)-N1,N3-bis(1-naphthyl)pyrene-5,9-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 20 - 100℃; Inert atmosphere;	5 Synthesis Example 5 Synthesis Example 5 10344] This example illustrates the preparation of a compound having Formula 11, Compound 27.10345] 1,3-Dibromo-7-tert-butyl-pyrene (0.606 g, 1.46 mmole), N-phenyl-1 -naphthylamine (0.672 g, 3.07 mmole), Pd2(dba)3 (0.027 g, 0.029 mmole), tri-tert-butyl-phosphine (0.012 g, 0.058 mmole) and toluene (100 ml) were added to 250 mE round bottom reaction flask at room temperature under nitrogen atmosphere. Afier that sodium tert-butoxide (0.308 g, 0.32 1 mmole) was added to the mixture and the resulting suspension stirred at room temperature for 5 mm, then heated to 1000 C. overnight. The reaction mixture was cooled down to ambient temperature, water (100 ml) added and mixture was stirred in the air for 30 mi Afier that organic layer was separated and passed through a filter filled with layers of celite, florisil and silica gel washing with toluene (100 mE). Solvent was removed on rotary evaporator, the residue was redissolved in dichloromethane, evaporated onto celite and subjected to separation on silica gel colunm using mixture of hexanes and dichloromethane as eluent. Chromatography was repeated one time more. All fractions containing the product combined, eluent evaporated, the residue dissolved in toluene and precipitated into methanol. Yield of 7-tert-butyl-N’,N3-bis(phenyl)-N’,N3- bis(1-naphthyl)-pyrene-5,9-diamine, Compound 27, 0.162 g (0.23 mmole, 16%). MS: MH+=693. ‘H-NMR: 1.52 (s, 9H), 6.67 (d, 4H, J=8.5 Hz), 6.81 (t, 2H, J=7.5 Hz), 7.01 (br s, 4H), 7.07 (d, 2H, J=8.5 Hz), 7.16-7.27 (m, 7H), 7.3-7.41 (m, 2H), 7.58 (d, 2H, J=2H), 7.77-7.81 (m, 4H), 7.90 (d, 2H, J=7.5 Hz), 8.07 (s, 1H), 8.09 (d, 2H, J=7.5 Hz). Purity by UPEC->99.9%.

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - US2017/29362, 2017, A1 Location in patent: Paragraph 0344; 0345

73
[ 90-30-2 ]
[ 14862-52-3 ]
[ 1630849-97-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: N-phenyl-1-naphthylamine; 1,3-dibromo-5-chlorobenzene With sodium t-butanolate In toluene for 0.333333h; Inert atmosphere; Stage #2: With di-tert-butyl[dichloro({di-tert-butyl[4-(dimethylamino)phenyl]phosphaniumyl})palladio][4-(dimethylamino)phenyl]phosphanium In toluene for 24.3333h; Inert atmosphere; Reflux;	1.1 Step 1. Take 1,3-dibromo-5-chlorobenzene (19.85g, 73.4mmol), N-phenyl-1-naphthylamine (32.19g, 146.8mmol), sodium tert-butoxide (21.14g, 220.2mmol) ) Put it into a three-necked flask, add toluene and bubbling nitrogen for 20 minutes. Then, the catalyst dichloride, di-tert-butyl-(4-dimethylaminophenyl)phosphorus palladium(II) (0.52g, 0.734mmol) was added to the three-necked flask, and nitrogen gas was continued for 20min, and the reaction was carried out at reflux temperature for 24h. After the reaction, the organic phase was obtained by filtration, concentrated, and the crude product was passed through a silica gel column to obtain compound 1-1 (28.88 g, yield 72%).
67%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 100℃; for 3h;	9.1 (1) Synthesis of Compound J15 The following reagents and solvent were charged into a reaction vessel. Tris(dibenzylideneacetone)dipalladium(0): 190 mg (0.21 mmol) Tri(t-butyl)phosphine: 170 mg (0.82 mmol) Toluene: 20 ml. Next, the reaction solution was stirred at room temperature for 15 minutes. After that, the following reagents were charged into the reaction solution. Compound J13: 560 mg (2.1 mmol) Compound J14: 1.0 g (4.6 mmol) t-Butoxysodium: 880 mg (9.1 mmol). Next, the reaction solution was heated to 100° C. and then stirred at the temperature (100° C.) for 3 hours. After the completion of the reaction, the reaction solution was cooled and then an organic layer was extracted with toluene. Next, the extracted organic layer was dried and then the solvent was removed by distillation under reduced pressure to provide a coarse product. Next, the coarse product was purified by silica gel column chromatography (developing solvent; heptane:toluene=3:1) to provide 760 mg (yield: 67%) of Compound J15.
53%	With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); sodium t-butanolate In toluene Inert atmosphere; Reflux;

Reference： [1]Current Patent Assignee: PEKING UNIVERSITY - CN112538022, 2021, A Location in patent: Paragraph 0039-0041
[2]Current Patent Assignee: CANON INC - US9755165, 2017, B2 Location in patent: Page/Page column 103; 104
[3]Wang, Tao; Shi, Ming; Fang, Daqi; He, Junpeng; Zhang, Meng; Zhang, Siwei; Wei, Guodan; Meng, Hong [Journal of Materials Chemistry C, 2021, vol. 9, # 9, p. 3247 - 3256]

74
[ 90-30-2 ]
C₃₆H₂₅ClSi [ No CAS ]
C₅₂H₃₇NSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; at 80℃; for 1h;Inert atmosphere;	The reaction vessel was charged with compound G (3.5 g, 6.72 mmol),<strong>[90-30-2]N-phenyl-1-naphthylamine</strong> (1.62 g, 7.39 mmol),Pd (dba) 2 (0.19 g, 0.34 mmol),Sodium t-butoxide (1.29 g, 13.43 mmol) was added and the atmosphere was replaced with argon.Then, dehydrated toluene (67 mL),(T-butyl) phosphine toluene solution (1.5 M, 0.90 mL, 1.34 mmol) was added thereto, followed by heating and stirring at 80 C for 1 hour.After cooling, water was added to the reaction solution to extract an organic layer. The obtained organic layer was dried over anhydrous magnesium sulfate, and after filtration, the filtrate was concentrated by a rotary rotary evaporator. The obtained crude product was purified by silica gel column chromatography (developing solvent: toluene and hexane), and the resulting solid was recrystallized from toluene and ethanol to give 4.5 g of a white powder solid as a target compound 14 at a yield of 95%

Reference： [1]Patent: KR2017/100698,2017,A .Location in patent: Paragraph 0166; 0175-0177

75
9-phenyl-1,4-dihydro-1,4-epiminonaphthalene [ No CAS ]
[ 90-30-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With toluene-4-sulfonic acid; In 1,2-dichloro-ethane; at 20 - 80℃; for 24h;Schlenk technique; Inert atmosphere;	General procedure: To an oven-dried Schlenk tube was added 9-phenyl-1,4-dihydro-1,4-epiminonaphthalene (0.5mmol, 1 equiv) and TsOH·H2O (0.1 mmol, 0.2 equiv). The tube was degassed with argon for three times. Then DCE (4 mL) was added via syringe under room temperature. The mixture was stirred at 80 oC until TLC indicated that the starting materials were completely consumed. Then the reaction mixture was cooled down to room temperature and it was quenched with water (20 mL) and extracted with ethyl ether (10 mL) for three times. The combined organic layers were dried with Na2SO4, filtered and concentrated. The crude products were purified using flash column chromatography on silica gel to afford the desired product.N-Phenylnaphthalen-1-amine (4)Prepared according to the general procedure 3 on 0.5 mmol scale and obtained an isolated yieldof 93% (102 mg) as a light gray solid. Spectral data is consistent with that of previous reported.[10]1H NMR (400 MHz, DMSO) delta 8.30 - 8.08 (m, 2H), 7.89 (m, 1H), 7.59 - 7.44 (m, 3H), 7.40 (t, J = 7.8Hz, 1H), 7.33 (d, J = 7.4 Hz, 1H), 7.22 (t, J = 7.9 Hz, 2H), 7.13 - 6.99 (m, 2H), 6.82 (t, J = 7.3 Hz,1H).13C NMR (100 MHz, DMSO) delta 145.0, 139.4, 134.4, 129.0, 128.1, 127.0, 126.1, 126.0, 125.0, 122.8,121.4, 119.5, 117.0, 114.1.

Reference： [1]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 354 - 363

76
[ 38303-35-4 ]
[ 90-30-2 ]
1,8-bis[N-(1-naphthyl)-N-phenylamino]pyrene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate In o-xylene at 125 - 130℃; for 3.5h; Inert atmosphere;	1,8-Bis[N-(1-naphthyl)-N-phenylamino]pyrene 3 The mixture of 5.4 g(0.015 mol) of 1,8-dibromopyrene, 8.3 g (0.038 mol) of N-phenyl-N-(1-naphthyl)amine, 80 mg of palladium diacetate, 280 mg of tri(tert-butyl)phosphine,3.8 g (0.04 mol) of sodium tert-butoxide and 100 ml of o-xylenewas heated up to 125-130°C. The reaction mixture was stirred at thistemperature under argon atmosphere for 3.5 h. After cooling to roomtemperature, the mixture was diluted with 100 ml of hexane and filteredfrom the precipitate (5.4 g, by-products), the filtrate was evaporated todryness. The residue was treated with 30 ml of acetone and then 30 ml ofmethanol was added to the mixture. Yellow precipitate was filtered, washedwith methanol, dried in vacuo over P2O5. Yield 3.81 g (40%). 1H NMR,δ: 6.70 (d, 4H, J 7.9 Hz), 6.84 and 6.85 (2 d, 2H, J 7.3 Hz), 7.08 and 7.09(2 d, 4H, J 7.9 Hz), 7.21 (d, 2H, J 6.9 Hz), 7.27-7.35 (m, 4H), 7.42 and7.44 (2 d, 2H, J 7.1 Hz), 7.68 (d, 2H, J 8.2 Hz), 7.74 (d, 2H, J 8.2 Hz),7.86 (d, 2H, J 8.1 Hz), 7.95 (s, 2 H), 8.02-8.08 (m, 4 H), 8.11 (s, 2H). IR (ν/cm-1): 3042, 1594 (C=C), 1574, 1504, 1490, 1460, 1421, 1393,1334, 1274, 1247, 1214, 1185, 1136, 1076, 1020, 968, 865, 850, 828,817, 798, 791, 774, 735, 696. MS, m/z: 636 [M]+. Found (%): C, 89.69;H, 5.26; N, 4.47. Calc. for C48H32N2 (%): C, 90.53; H, 5.07; N, 4.40.

Reference： [1]Kaplunov, Mikhail G.; Yakushchenko, Igor K.; Krasnikova, Svetlana S.; Echmaev, Sergei B. [Mendeleev Communications, 2016, vol. 26, # 5, p. 437 - 439]

77
[ 90-30-2 ]
[ 5467-74-3 ]
[ 717888-41-0 ]

Yield	Reaction Conditions	Operation in experiment
73.3%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 50 - 110℃; for 15h;	2.1 Step 1. N- phenyl-1-naphthalene-amine (7.50g, 34.2mmol) and (4-bromophenyl) boronic acid (7.56 g, 37.6 mmol),Sodium-t-butoxide (8.2 g, 2.5 eq) was dissolved in anhydrous toluene,(50 wt% in toluene, 10.38 g, 51.3 mmol) and Pd 2 (dba) 3 (6.26 g, 6.8 mmol) were slowly added to the reaction mixture, and the reaction was carried out at 110 ° C.After 15 hours, excess water was added to the reaction mixture, and the organic material was extracted with dichloromethane (2x60 ml).The obtained organic substance was purified through recrystallization (n-hexane: ethylacetate, 8: 1)(4- (naphthalen-1-yl (phenyl) amino) phenyl) boronic acid as a white solid (8.5 g, 73.3%).

Reference： [1]Current Patent Assignee: KOREA NATIONAL UNIVERSITY OF TRANSPORTATION INDUSTRY - KR2018/105918, 2018, A Location in patent: Paragraph 0114-0117

78
[ 90-30-2 ]
5,5'-(4'-bromobiphenyl-3,5-diyl)bis(1-phenyl-1H-indole) [ No CAS ]
C₅₆H₃₉N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 100℃;	To a round bottom flask was added 5,5'- 4'-bromobiphenyl-3,5-diyl) bis (1-phenyl-1H-indole) (14.77 g, 24 mmol), Nphenylnaphthalen-1-amine (4.39 g, 20 mmol), Pd2 (dba) 3 (0.03-0.05 mmol), P (t-Bu) 3 (0.1 equivalent), NaOt-Bu (3 eq.), toluene (10.5 mL / 1 mmol) is added and the reaction proceeds at 100 C. After the reaction was completed, the reaction mixture was extracted with ether and water and then The organic layer was dried over MgSO 4 and concentrated and then The resulting organic material was purified by silicagel column and recrystallized to obtain 10.10 g (yield: 67%) of the product.
67%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 100℃;	In a round bottom flask 5,5'-(4'-bromobiphenyl-3,5-diyl)bis(1-phenyl-1H-indole) (14.77g, 24mmol), N-phenylnaphthalen-1-amine (4.39g, 20mmol), Pd2(dba)3 (0.03~0.05 mmol), P(t-Bu)3 0.1 eq.), NaOt-Bu (3 eq.),toluene (10.5 mL / 1 mmol) is added and the reaction proceeds at 100 C.After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO 4 and concentrated. The resulting organic material was purified by silicagel column and recrystallized to obtain 10.10 g (yield: 67%) of the product.

Reference： [1]Patent: KR2018/122984,2018,A .Location in patent: Paragraph 0138-0140
[2]Patent: KR101952234,2019,B1 .Location in patent: Paragraph 0122-0124

79
[ 90-30-2 ]
1,1'-(4'-bromobiphenyl-3,5-diyl)bis(1H-indole) [ No CAS ]
C₄₄H₃₁N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 100℃;	To a round bottom flask was added 1,1 '- (4'-bromobiphenyl-3,5-diyl) bis (1H-indole) (11.12g, 24mmol), N-phenylnaphthalen-1-amine (4.39 g, 20 mmol), Pd2 (dba) 3 (0.03-0.05 mmol), P (t-Bu) 3 (0.1 equivalent), NaOt-Bu (3 eq.), toluene (10.5 mL / 1 mmol) was added and the reaction was carried out at 100 C. After the reaction was completed, the reaction mixture was extracted with ether and water and then The organic layer was dried over MgSO 4 and concentrated and then The resulting organic material was subjected to silicagel column and recrystallization to obtain 8.18 g (yield: 68%) of the product.
68%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 100℃;	In a round bottom flask 1,1'-(4'-bromobiphenyl-3,5-diyl)bis(1H-indole) (11.12g, 24mmol), N-phenylnaphthalen-1-amine (4.39g, 20mmol), Pd2(dba)3 (0.03~0.05 mmol), P(t-Bu)3 (0.1 eq.), NaOt-Bu (3 eq.), toluene (10.5 mL / 1 mmol) is added and the reaction proceeds at 100 C. After the reaction was completed, the reaction mixture was extracted with ether and water. The organic layer was dried over MgSO 4 and concentrated. The resulting organic material was subjected to silicagel column and recrystallization to obtain 8.18 g (yield: 68%) of the product.

Reference： [1]Patent: KR2018/122984,2018,A .Location in patent: Paragraph 0123-0125
[2]Patent: KR101952234,2019,B1 .Location in patent: Paragraph 0107-0109

80
[ 90-30-2 ]
[ 1239327-73-1 ]
C₅₈H₅₂N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium t-butanolate In toluene for 18h; Inert atmosphere; Sealed tube; Reflux;

Reference： [1]Shukla, Jyoti; Ajayakumar; Mukhopadhyay, Pritam [Organic Letters, 2018, vol. 20, # 24, p. 7864 - 7868]

81
[ 143-66-8 ]
[ 134-32-7 ]
[ 90-30-2 ]

Yield	Reaction Conditions	Operation in experiment
73%	With copper(II) acetate monohydrate; triethylamine; In acetonitrile; at 20℃; for 24h;	General procedure: A 10 mL vial was charged with the substrate amine 1 (0.2 mmol), NaBPh4 or NaBAr4 (0.1 mmol), and Cu(OAc)2·H2O (0.2 equiv) in MeCN (2 mL). To this mixture was added Et3N (2.0 equiv). The reaction mixture was then stirred at r.t. for 24 h. After completion of the reaction as monitored by TLC, the mixture was then concentrated through a rotary evaporator to yield the product, which was purified by direct flash column chromatography (Tables 2 and 3).

Reference： [1]Synthesis,2019,vol. 51,p. 538 - 544

82
[ 90-30-2 ]
[ 633-70-5 ]
2,6-bis[N-(naphthalen-1-yl)-N-phenylamino]anthraquinone [ No CAS ]

Reference： [1]Journal of the Chinese Chemical Society,2019,vol. 66,p. 1550 - 1560

83
[ 90-30-2 ]
C₃₃H₂₅BrClN [ No CAS ]
C₄₉H₃₇ClN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.4%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 105℃; for 24h;Inert atmosphere;	(2) at a 250ml three-necked flask, nitrogen protection, was added 0.012mol of Intermediate M-8,0.01mol material A-12,150ml stirred mixture of toluene, followed by addition of 5×10-5mol Pd2(dba)3,. 5 × 10-5mol tri-tert-butyl phosphine, 0.03 mol of sodium tert-butoxide and heated to 105 deg.] C, the reaction was refluxed for 24 hours, and sampling showed no residual amino compound, the reaction was complete; cool to room temperature, filtered, The filtrate was rotary evaporated until no fraction, through neutral silica gel column chromatography to give the intermediate N-1, purity 99.7%, yield 85.4%.

Reference： [1]Patent: CN109836339,2019,A .Location in patent: Paragraph 0112-0113; 0116-0117

84
[ 16807-11-7 ]
[ 90-30-2 ]
1-[1-naphthyl(phenyl)amino]carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 17h; Inert atmosphere;	32 Example-32 In an argon atmosphere, 1-bromocarbazole (125 mg, 0.509 mmol), 1-naphthyl (phenyl) amine (557 mg, 2.54 mmol),Sodium tert-butoxide (483 mg, 5.03 mmol), tris (dibenzylideneacetone) dipalladium / chloroform adduct (28 mg, 27 μmol)Toluene and tri-tert-butylphosphonium tetrafluoroborate (39 mg, 0.13 mmol) were added toluene (5 mL), and the mixture was stirred at 110 ° C. for 17 hours.After cooling to room temperature, 1M HCl aqueous solution (10 mL) was added, and the mixture was stirred at room temperature for 5 minutes, and then the organic layer was extracted with ethyl acetate.The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (hexane / triethylamine = 9/1).The obtained crude product was washed with methanol and dried under reduced pressure.The target 1- [1-naphthyl (phenyl) amino] carbazole was obtained as a pale yellow solid (82 mg, 0.21 mmol, 42% yield).

Reference： [1]Current Patent Assignee: SAGAMI CHEMICAL RESEARCH INSTITUTE; TOSOH CORPORATION - JP2019/137613, 2019, A Location in patent: Paragraph 0136-0138

85
[ 67665-47-8 ]
[ 90-30-2 ]
C₅₇H₃₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate; In toluene; at 110℃; for 20h;Inert atmosphere;	Under a nitrogen atmosphere,Adding 2,2'-dibromo-9,9'-spirobifluorene (0.7 g, 1.48 mmol),<strong>[90-30-2]N-phenyl-1-naphthylamine</strong> (0.97 g, 4.44 mmol),Palladium acetate (18mg, 0.082mmol),Cesium carbonate (1.74g, 5.33mmol)And tri-tert-butylphosphine (0.038mL, 0.15mmol) in toluene (10mL)Heat and stir at 110 C for 20 hours.After cooling to room temperature,The reaction was quenched with a saturated ammonium chloride solution.The aqueous layer was extracted three times with ethyl acetate,The combined organic phases were washed with a saturated aqueous sodium chloride solution.After the organic phase was dried over anhydrous sodium sulfate,The solvent was evaporated to dryness under reduced pressure,The obtained product was further purified by silica gel column chromatography,Petroleum ether / ethyl acetate (10: 1, v / v) was used as the eluent.Get pure product,As a white solid.Yield: 96% (1.0 g).

Reference： [1]Patent: CN110790629,2020,A .Location in patent: Paragraph 0141; 0142; 0143; 0144; 0145; 0146; 0147-0150

86
[ 90-30-2 ]
C₂₆H₁₂Br₂ [ No CAS ]
C₅₈H₃₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos; In toluene; at 100 - 110℃; for 3h;Inert atmosphere;	(2) To the machine equipped with mechanical stirring, thermometer, After replacing the three-port reaction flask in the condenser with nitrogen, Add intermediate 39c (20mmol) in sequence, Intermediate 4 (10mmol), 90ml toluene, Heating to reflux for 0.5h, Cool down to 70-80 C , Slowly add sodium tert-butoxide (30mmol), Pd2 (dba) 3 (0.1mmol), xphos (0.5mmol), After the system is stable, it is heated to 100 ~ 110 C for 3 hours. Cool down to 25-30 C , add 60ml water, 50ml toluene was stirred and separated, The aqueous phase was extracted once with 100ml toluene, Separate the liquid and combine the organic phases, Add 8g of anhydrous sodium sulfate to the organic phase, stir and dry, Filtration, the organic phase is concentrated (-0.08 0.09MPa, 55-60 C ) until it does not come out, Add 20ml of petroleum ether with stirring, Cool down 0-5C , filter, 6.7 g of compound 39 was obtained with a yield of 88%.

Reference： [1]Patent: CN111018722,2020,A .Location in patent: Paragraph 0192; 0195-0196

87
[ 610-97-9 ]
[ 90-30-2 ]
[ 2363738-58-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With copper(l) iodide; 18-crown-6 ether; potassium carbonate In 1,2-dichloro-benzene at 175℃; Inert atmosphere;	Synthesis of methyl 2-(naphthalen-1-yl(phenyl)amino)benzoate (B) The mixture of methyl 2-iodobenzoate (1.02 g,3.07 mmol), N-phenylnaphthalen-1-amine (1.25 g, 5.73 mmol), K2CO3(1.38 g, 9.96 mmol), CuI (50.8 mg, 0.27 mmol), and 18-crown-6(148 mg, 0.56 mmol) were dissolved with o-DCB (5 ml) in a 100 mlround-bottom flask under nitrogen atmosphere was heated at 175 °Cand stirred overnight. After cooling to room temperature, the reactionmixture was purified by silica gel column chromatography using petroleumether/CH2Cl2 mixed solvent as eluent. Yellow solid as compoundB with a yield of 75% was obtained after drying in vacuum oven.The solid was directly used for the next step.

Reference： [1]Gao, Yongqian; Huang, Wei; Li, Jiewei; Li, Yihao; Lin, Jinyi; Wang, Jianfeng; Wang, Zepeng; Weng, Jiena; Yan, Bohan; Yu, Yang; Zhao, Jianfeng; Zhao, Qiang; Zhao, Xianghua [Dyes and Pigments, 2019, vol. 170]

88
[ 90-30-2 ]
[ 832080-63-4 ]
[ 2482614-68-4 ]

Yield	Reaction Conditions	Operation in experiment
84.24%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate In toluene at 100℃; for 24h; Inert atmosphere;	2.4.2 General Procedure for the synthesis of N,N-diaryl-2,3-di(hetero-2-yl)pyrido[2,3-b]pyrazin-7-amine General procedure: To a mixture of compound 1 or 7 (1.0mmol) and various secondary amine (1.0mmol) in anhydrous toluene (50mL)was added Pd2(dba)3 (0.02mmol), SPhos (0.048mmol) and NaOtBu (0.144mmol). The reaction was stirred under nitrogen atmosphere at 100°C for 24h. After the completion of reaction, the reaction mixture was cooled to room temperature and extracted with chloroform (3×50 ml) followed by water wash (3×50 ml). All organic layers were combined and dried over anhydrous Na2SO4, filtered and distilled to get the crude product which was further purified by silica gel column chromatography (eluent: n-hexane: chloroform) to afford the pure product.

Reference： [1]Garud, Dinesh R.; Kamble, Rajesh M.; Mahadik, Suraj S.; Pingale, Subhash S.; Ware, Anuja P. [Dyes and Pigments, 2021, vol. 184]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	90-30-2	MDL No. :	MFCD00003878
Formula :	C₁₆H₁₃N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XQVWYOYUZDUNRW-UHFFFAOYSA-N
M.W :	219.28	Pubchem ID :	7013
Synonyms :

Num. heavy atoms :	17
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	73.49
TPSA :	12.03 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.66 cm/s

[ CAS No. 90-30-2 ] {[proInfo.proName]}

Quality Control of [ 90-30-2 ]

Related Doc. of [ 90-30-2 ]

Product Details of [ 90-30-2 ]

Calculated chemistry of [ 90-30-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 90-30-2 ]

Application In Synthesis of [ 90-30-2 ]

[ 90-30-2 ] Synthesis Path-Upstream 1~1

[ 90-30-2 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Log Po/w (iLOGP) :	2.61
Log Po/w (XLOGP3) :	4.2
Log Po/w (WLOGP) :	4.58
Log Po/w (MLOGP) :	4.19
Log Po/w (SILICOS-IT) :	3.8
Consensus Log Po/w :	3.88

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

Log S (ESOL) :	-4.41
Solubility :	0.00853 mg/ml ; 0.0000389 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.16
Solubility :	0.0151 mg/ml ; 0.0000688 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.65
Solubility :	0.0000493 mg/ml ; 0.000000225 mol/l
Class :	Poorly soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.82

Signal Word:	Danger	Class:	9
Precautionary Statements:	P260-P264-P270-P272-P273-P280-P301+P312+P330-P302+P352-P314-P333+P313-P391-P501	UN#:	3077
Hazard Statements:	H302-H317-H372-H410	Packing Group:	Ⅲ
GHS Pictogram:

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Code	Phrase
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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
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
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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.
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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.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
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