Name: 58743-83-2|4-Bromo-4'-methoxy-1,1'-biphenyl|98%
Brand: Ambeed
SKU: A285852
Price: 13.0 USD
Availability: InStock
Rating: 93 (26 reviews)

1
[ 29558-77-8 ]
[ 77-78-1 ]
[ 58743-83-2 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 5253 - 5263
[2]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 11 - 23
[3]Journal of the Chemical Society,1936,p. 802,806
[4]Molecular Crystals and Liquid Crystals (1969-1991),1985,vol. 131,p. 1 - 8

2
[ 58743-83-2 ]
[ 105-58-8 ]
[ 96871-79-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; hexane at -76℃; for 0.666667h; Stage #2: Diethyl carbonate In tetrahydrofuran; hexane at 25℃; for 1h; Inert atmosphere;	Synthesis of 26 n-BuLi (2.7M solution in hexane, 1.5 mL, 1.1 equiv) was added over 10 min to a solution of 25 (0.90 g, 3.4 mmol) in dry THF (15 mL) at -76 °C. The reaction was allowed for 40 min. A solution of diehtylcarbonate (0.13 mL, 1.1 mmol) in dry THF (2 mL) was dropwised to the reaction mixture. And then the reaction mixture was stirred at room temperature for 1 h under Ar. The solution was poured into brine (10 mL) and CHCl3 (20 mL). Aqueous layer was extracted with CHCl3 for two times. The combined organic layer was washed with water and dried over MgSO4. A residual liquid was purifiedby column chromatography (EtOAc/Hex = 1/5) to give the compound 26 (0.51 g, 81%).
	With sodium; benzene

Reference： [1]Kim, Nam-Kyun; Sogawa, Hiromitsu; Takata, Toshikazu [Tetrahedron Letters, 2020, vol. 61, # 23]
[2]Morton; Emerson [Journal of the American Chemical Society, 1938, vol. 60, p. 284]

3
[ 2314-97-8 ]
[ 58743-83-2 ]
[ 10355-12-1 ]

Yield	Reaction Conditions	Operation in experiment
40%	With copper In N,N-dimethyl-formamide at 150℃; for 20h; in autoclave;

Reference： [1]Barny, P. le; Ravaux, G.; Dubois, J. C.; Parneix, J. P. [Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 127, p. 413 - 430]

4
[ 29558-77-8 ]
[ 74-88-4 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N-methyl-acetamide; water;	Part A: To a solution of 12.4 grams (5.0 mmol) of 4-(4'-bromophenyl)phenol in 50 mL of dimethylformamide was added 10.1 grams of potassium carbonate followed by 10.51 grams of iodomethane and this stirred at room temperature for 48 hours. The solution was diluted with 400 mL of water and extracted with ethyl acetate. The organics were dried over magnesium sulfate filtered and concentrated to yield 14.1 grams of crude product. Purification by recrystallization from ethyl acetate hexane gave 8.2 grams of 4-(4'-bromophenyl)anisole as a white crystalline solid.

Reference： [1]Journal of Heterocyclic Chemistry,2007,vol. 44,p. 853 - 862
[2]Angewandte Chemie - International Edition,2007,vol. 46,p. 6807 - 6810
[3]Chemical Communications,2015,vol. 51,p. 12641 - 12644
[4]Molecular Crystals and Liquid Crystals (1969-1991),1985,vol. 127,p. 413 - 430
[5]Journal of Fluorine Chemistry,2006,vol. 127,p. 620 - 626
[6]Patent: US6747027,2004,B1

5
[ 75-77-4 ]
[ 58743-83-2 ]
[ 17964-17-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at 20℃; for 4h; Further stages.;
	(i) nBuLi, Et₂O, benzene, (ii) /BRN= 1209232/; Multistep reaction;

Reference： [1]Moon, Kyung-Soo; Kim, Ho-Joong; Lee, Eunji; Lee, Myongsoo [Angewandte Chemie - International Edition, 2007, vol. 46, # 36, p. 6807 - 6810]
[2]Baker,R. et al. [Journal of the Chemical Society, 1964, p. 627 - 633]

6
[ 58743-83-2 ]
[ 126971-87-7 ]

Yield	Reaction Conditions	Operation in experiment
60%	With iodine; sodium iodide In acetonitrile at 20℃; for 36h; Inert atmosphere; UV-irradiation; Green chemistry;
	Multistep reaction;

Reference： [1]Li, Lu; Liu, Wenbo; Zeng, Huiying; Mu, Xiaoyue; Cosa, Gonzalo; Mi, Zetian; Li, Chao-Jun [Journal of the American Chemical Society, 2015, vol. 137, # 26, p. 8328 - 8331]
[2]Spivey, Alan C.; Diaper, Christopher M.; Rudge, Andrew J. [Chemical Communications, 1999, # 9, p. 835 - 836]

7
[ 58743-83-2 ]
[ 58743-77-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With iodophenylbis(triphenylphosphine)palladium In N,N-dimethyl-formamide for 2h; Heating;

Reference： [1]Bumagin, N. A.; Luzikova, E. V.; Beletskaya, I. P. [Russian Journal of Organic Chemistry, 1995, vol. 31, # 11, p. 1480 - 1486][Zhurnal Organicheskoi Khimii, 1995, vol. 31, # 11, p. 1650 - 1656]

8
[ 232946-70-2 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
4 mg	Stage #1: 4-{2-[(4'-methoxy-biphenyl-4-yl)-dimethyl-germanyl]-ethyl}-phenol With Argogel; tributylphosphine; diamide In benzene for 16h; Stage #2: With bromine In dichloromethane at 20℃; for 0.666667h; Further stages.;

Reference： [1]Spivey, Alan C.; Diaper, Christopher M.; Adams, Harry; Rudge, Andrew J. [Journal of Organic Chemistry, 2000, vol. 65, # 17, p. 5253 - 5263]

9
4-[2-dimethyl-(4,4'-biphenylmethoxy)germylethyl]phenyl ethoxyethyl ether [ No CAS ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With bromine In dichloromethane at 20℃; for 0.333333h;

Reference： [1]Spivey, Alan C.; Diaper, Christopher M.; Adams, Harry; Rudge, Andrew J. [Journal of Organic Chemistry, 2000, vol. 65, # 17, p. 5253 - 5263]

10
[ 589-87-7 ]
[ 22868-26-4 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; silver(l) oxide In tetrahydrofuran at 60℃; for 36h;
60%	With silver(l) oxide In tetrahydrofuran at 60℃; for 36h;

Reference： [1]Hirabayashi, Kazunori; Mori, Atsunori; Kawashima, Jun; Suguro, Masahiro; Nishihara, Yasushi; Hiyama, Tamejiro [Journal of Organic Chemistry, 2000, vol. 65, # 17, p. 5342 - 5349]
[2]Hirabayashi, Kazunori; Kawashima, Jun; Nishihara, Yasushi; Mori, Atsunori; Hiyama, Tamejiro [Organic Letters, 1999, vol. 1, # 2, p. 299 - 301]

11
[ 1445-73-4 ]
[ 58743-83-2 ]
[ 342889-43-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; hexane at -40℃; Stage #2: 1-Methyl-4-piperidone In tetrahydrofuran; hexane at -50 - -20℃; for 1.5h;

Reference： [1]Kelley; Ansu; Budisusetyo; Ghiorghis; Qin; Kauffman [Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 11 - 23]

12
[ 201230-82-2 ]
[ 5720-07-0 ]
[ 673-40-5 ]
[ 58743-83-2 ]
[ 54118-75-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 76% 2: 12%	With palladium diacetate; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In 1,4-dioxane at 100℃; for 5h;

Reference： [1]Andrus, Merritt B.; Ma, Yudao; Zang, Yunfu; Song, Chun [Tetrahedron Letters, 2002, vol. 43, # 50, p. 9137 - 9140]

13
[ 5720-07-0 ]
[ 147227-33-6 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
40 % Chromat.	With boron trifluoride diethyl etherate In 1,2-dimethoxyethane; hexane at 20℃; for 1h;

Reference： [1]Saeki, Tomoyuki; Son, Eun-Cheol; Tamao, Kohei [Organic Letters, 2004, vol. 6, # 4, p. 617 - 619]

14
[ 5720-07-0 ]
[ 106-40-1 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: 4-bromo-aniline With tert.-butylnitrite; boron trifluoride diethyl etherate In methanol at 0℃; for 0.5h; Schlenk technique; Stage #2: 4-methoxyphenylboronic acid In methanol at 0 - 60℃; for 5h; Schlenk technique;
65%	Stage #1: 4-bromo-aniline With tert.-butylnitrite; boron trifluoride diethyl etherate at -15 - 5℃; for 0.583333h; Stage #2: 4-methoxyphenylboronic acid With (R,R)-N,N'-(2-MeC₆H₄)2-N,N'-(cyclohexane-1,2-diyl)thiourea In methanol at 20℃; for 4h;

Reference： [1]Zong, Yan; Hu, Jiefeng; Sun, Peipei; Jiang, Xiaoqing [Synlett, 2012, vol. 23, # 16, p. 2393 - 2396]
[2]Dai, Mingji; Liang, Bo; Wang, Cuihua; Chen, Jiahua; Yang, Zhen [Organic Letters, 2004, vol. 6, # 2, p. 221 - 224]

Yield	Reaction Conditions	Operation in experiment
32%	With acetic acid; sodium bromide; metsulfovax at 25℃; for 1h;

16
[ 106-37-6 ]
[ 5720-07-0 ]
[ 58743-83-2 ]
[ 13021-19-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 30% 2: 22%	With disodium[(N,N’-bis(2-hydroxy-5-sulfonatobenzyl)-1,2-diphenyl-1,2-diaminoethano)palladate(II)]; caesium carbonate In water at 80℃; for 1h;	Catalysis experiments and gas chromatographic analysis of the reaction mixtures General procedure: Stock solutions of the catalysts (Na2[Pd(HSS)], Na2[Pd(PrHSS)], Na2[Pd(BuHSS)],Na2[Pd(dPhHSS)], rac-Na2[Pd(CyHSS)], Na2[Pd(cis-CyHSS)]) Na2[Pd(trans-CyHSS)]) were prepared by dissolving 5.0×10-7 mol complex in 6 mL water. In general, 0.5 mmol aryl-halide, 0.75 mmol boronic acid derivative (1.5 mmol in the reactions of aryl-dihalides), and 0.5 mmolbase (Cs2CO3) were used in each reaction. Good quality distilled water was used as solvent, the organic phase was comprised of the substrates. 3 mL of water was used in each reaction. The reactions were carried out at 80 °C in 30-120 min reaction time. At the end of the reactions, the mixtures were allowed to cool to room temperature and then were extracted by chlorofom (2 mL). After separation of the phases (15-20 min) the organic phase was removed by a Pasteur pipette and filtered through a short MgSO4 plug.
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In methanol; toluene Heating;

Reference： [1]Bunda, Szilvia; Joó, Ferenc; Kathó, Ágnes; Udvardy, Antal; Voronova, Krisztina [Molecules, 2020, vol. 25, # 17]
[2]Sinclair, David J.; Sherburn, Michael S. [Journal of Organic Chemistry, 2005, vol. 70, # 9, p. 3730 - 3733]

17
C₁₃H₁₁BrN₄O₃ [ No CAS ]
[ 5720-07-0 ]
[ 58743-83-2 ]
[ 97-52-9 ]

Yield	Reaction Conditions	Operation in experiment
	With boron trifluoride diethyl etherate In methanol at 20℃; for 3h;

Reference： [1]Saeki, Tomoyuki; Son, Eun-Cheol; Tamao, Kohei [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 9, p. 1654 - 1658]

18
[ 58743-83-2 ]
[ 156642-03-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With n-butyllithium; Trimethyl borate; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 20℃; for 1h;
	Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78 - -65℃; Stage #2: With Trimethyl borate In tetrahydrofuran; hexane at -65 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane at 20℃; Further stages.;
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere 1.2: 17 h / -78 - 66 °C / Inert atmosphere 2.1: hydrogenchloride / water; tetrahydrofuran / 2 h / 23 °C / Inert atmosphere

Reference： [1]Katagiri, Toshifumi; Ota, Satoshi; Ohira, Takayuki; Yamao, Takeshi; Hotta, Shu [Journal of Heterocyclic Chemistry, 2007, vol. 44, # 4, p. 853 - 862]
[2]Zang, Zhi-Qian; Zhang, Dong; Wan, Xin-Hua; Zhou, Qi-Feng [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158]
[3]Oesch, David; Luedtke, Nathan W. [Chemical Communications, 2015, vol. 51, # 63, p. 12641 - 12644]

19
[ 58743-83-2 ]
[ 76-05-1 ]
[ 134249-43-7 ]

Yield	Reaction Conditions	Operation in experiment
31.6%	Stage #1: 4-bromo-4'-methoxylbiphenyl With magnesium In tetrahydrofuran at 60℃; for 4h; Stage #2: trifluoroacetic acid With sodium hydride In tetrahydrofuran at 0℃; for 36h; Further stages.;

Reference： [1]Tojo, Kenta; Aoki, Yoshio; Yasutake, Mikio; Hirose, Takuji [Journal of Fluorine Chemistry, 2006, vol. 127, # 4-5 SPEC. ISS., p. 620 - 626]

20
[ 104-92-7 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: BuLi / diethyl ether; hexane / 1 h / -78 °C 1.2: 63 percent / diethyl ether; hexane / 13 h / 20 °C 2.1: 60 percent / Ag₂O / Pd(PPh₃)4 / tetrahydrofuran / 36 h / 60 °C
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hydroxide; tetrabutylammomium bromide / water / 0.07 h / 100 °C / Microwave irradiation 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium hydroxide; tetrabutylammomium bromide; copper(l) iodide / water / 0.1 h / 100 °C / Microwave irradiation

Reference： [1]Hirabayashi, Kazunori; Kawashima, Jun; Nishihara, Yasushi; Mori, Atsunori; Hiyama, Tamejiro [Organic Letters, 1999, vol. 1, # 2, p. 299 - 301]
[2]Tan, Xin; Zhou, Zi Jie; Zhang, Jia Xin; Duan, Xin Hong [European Journal of Organic Chemistry, 2014, vol. 2014, # 24, p. 5153 - 5157]

21
[ 148-86-7 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 84.6 percent / Na₂CO₃; Br₂ / 1,2-dichloro-ethane / 50 °C 2: 83.8 percent / NaOH / H₂O; ethanol / 6 h / Heating 3: sodium hydroxide / ethanol; H₂O / Heating
	Multi-step reaction with 3 steps 1: Br₂, (CF₃CO)2O / FeCl₃ / CCl₄ 2: KOH / ethanol 3: K₂CO₃ / acetone

Reference： [1]Zang, Zhi-Qian; Zhang, Dong; Wan, Xin-Hua; Zhou, Qi-Feng [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2000, vol. 339, p. 145 - 158]
[2]Surendranath, V.; Fishel, D. L.; Vries, A de; Mahmood, R.; Johnson, D. L. [Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 131, p. 1 - 8]

22
[ 58743-83-2 ]
[ 342889-40-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran; hexane / -40 °C 1.2: 72 percent / tetrahydrofuran; hexane / 1.5 h / -50 - -20 °C 2.1: 69 percent / 10 percent Pd/C / diphenyl ether / 24 h / 230 - 255 °C

Reference： [1]Kelley; Ansu; Budisusetyo; Ghiorghis; Qin; Kauffman [Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 11 - 23]

23
[ 58743-83-2 ]
[ 342889-60-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran; hexane / -40 °C 1.2: 72 percent / tetrahydrofuran; hexane / 1.5 h / -50 - -20 °C 2.1: 69 percent / 10 percent Pd/C / diphenyl ether / 24 h / 230 - 255 °C 3.1: 6.3 g / m-CPBA; NaHCO₃ / CHCl₃ / 15 h / Heating

Reference： [1]Kelley; Ansu; Budisusetyo; Ghiorghis; Qin; Kauffman [Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 11 - 23]

24
[ 58743-83-2 ]
2-(4-methoxyphenyl)-4-(4''-methoxybiphenyl-4-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran; hexane / -40 °C 1.2: 72 percent / tetrahydrofuran; hexane / 1.5 h / -50 - -20 °C 2.1: 69 percent / 10 percent Pd/C / diphenyl ether / 24 h / 230 - 255 °C 3.1: 6.3 g / m-CPBA; NaHCO₃ / CHCl₃ / 15 h / Heating 4.1: ClCO₂Et / tetrahydrofuran / 0.33 h / 20 °C 4.2: 24 percent / tetrahydrofuran / 0.5 h / -70 °C

Reference： [1]Kelley; Ansu; Budisusetyo; Ghiorghis; Qin; Kauffman [Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 11 - 23]

25
[ 58743-83-2 ]
4-(4'-methoxybiphenyl-4-yl)-1-(3-sulfobutyl)pyridinium zwitterion [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-BuLi / tetrahydrofuran; hexane / -40 °C 1.2: 72 percent / tetrahydrofuran; hexane / 1.5 h / -50 - -20 °C 2.1: 69 percent / 10 percent Pd/C / diphenyl ether / 24 h / 230 - 255 °C 3.1: 85 percent / benzonitrile / 0.5 h / Heating

Reference： [1]Kelley; Ansu; Budisusetyo; Ghiorghis; Qin; Kauffman [Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 11 - 23]

26
[ 58743-83-2 ]
2-(2-hydroxy-5-methylphenyl)-4-(4'-methoxybiphenyl-4-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-BuLi / tetrahydrofuran; hexane / -40 °C 1.2: 72 percent / tetrahydrofuran; hexane / 1.5 h / -50 - -20 °C 2.1: 69 percent / 10 percent Pd/C / diphenyl ether / 24 h / 230 - 255 °C 3.1: 6.3 g / m-CPBA; NaHCO₃ / CHCl₃ / 15 h / Heating 4.1: ClCO₂Et / tetrahydrofuran / 0.5 h / 25 °C 4.2: 2 percent / tetrahydrofuran / 3 h / -50 °C

Reference： [1]Kelley; Ansu; Budisusetyo; Ghiorghis; Qin; Kauffman [Journal of Heterocyclic Chemistry, 2001, vol. 38, # 1, p. 11 - 23]

27
[ 2170-13-0 ]
[ 58743-83-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 11 - 23

28
[ 58743-83-2 ]
[ 40501-41-5 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1985,vol. 131,p. 1 - 8

29
[ 58743-83-2 ]
4-bromo-2-methyl-2H-pyrazol-3-ylamine [ No CAS ]
(4-bromo-2-methyl-2H-pyrazol-3-yl)-(4'-methoxy-biphenyl-4-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate In toluene at 80℃; for 48h;	1.19 Example 1.19; Preparation of (4-Bromo-2-methyl-2H-pyrazol-3-yl)-(4'-methoxy-biphenyl-4-yI)-amine(Compound 13).A 20-mL scintillation vial was charged with 4'-bromo-4-methoxy-biphenyl (263.1 mg, 1 mmol), 3-amino-4-bromo-2-methyl pyrazole (176.0 mg, 1 mmol), sodium fert-butoxide (134.5 mg, 1.4 mmol), tris(dibenzylideneacetone)dipalladium(0) (45.8 mg, 0.05 mmol), BESfAP (62.3 mg, 0.1 mmol) and toluene (2 mL) under nitrogen atmosphere. The reaction mixture was heated at 800C for 48 hours. It was then allowed to cool to room temperature, taken up in ether/ethyl acetate, filtered and concentrated. The crude material was subjected to column chromatography on silica gel (Biotage, eluent hexanes/ethyl acetate 70/30) to afford Compound 13 as a yellow solid. LCMS m/z (%) = 358 (M+H 79Br, 100), 360 (M+H 81Br, 98).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2006/60762, 2006, A2 Location in patent: Page/Page column 72

30
[ 106-37-6 ]
[ 5720-07-0 ]
[ 497-19-8 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dimethoxyethane; ethyl acetate	1.i (i) (i) Production of 4-bromo-4'-methoxy-1,1'-biphenyl Under an argon atmosphere, p-dibromobenzene (9.99 g), 4-methoxyphenylboronic acid (2.03 g) and tetrakistriphenylphosphine palladium (497 mg) were dissolved in dimethoxyethane (20 ml). A 2M aqueous sodium carbonate solution (20 ml) was added and the mixture was heated under reflux for 14 h. The reaction mixture was cooled to room temperature and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in ethyl acetate and insoluble materials were filtered off. The solvent was evaporated and the obtained solid was washed with hexane to give the title compound (2.09 g) as a colorless solid. 1H-NMR (CDCl3) δ: 3.84 (3H, s), 6.97 (2H, d, J=8.8 Hz), 7.37-7.56 (6H, m). IR (KBr): 1483, 1291, 1258, 1038, 812 cm-1.

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US6518257, 2003, B1

31
[ 58743-83-2 ]
ammonium chloride [ No CAS ]
[ 247174-71-6 ]
[ 337534-45-9 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium In tetrahydrofuran; hexane	1.ii (ii) (ii) Production of 1-(1H-imidazol-4-yl)-1-(4'-methoxy-[1,1'-biphenyl]-4-yl)-2-methyl-1-propanol 4-Bromo-4'-methoxy-1,1'-biphenyl (1.95 g) was dissolved in THF (40 ml) and the mixture was cooled to -78° C. A solution (1.6 M; 5.5 ml) of n-butyllithium in hexane was added dropwise, and the mixture was stirred at -78° C. for 1 h. Then, a solution (10 ml) of 1-(1H-imidazol-4-yl)-2-methyl-1-propanone (335 mg) in THF was slowly added dropwise. The reaction mixture was heated from -78° C. to room temperature and saturated aqueous ammonium chloride solution was added to the reaction mixture. The mixture was extracted with ethyl acetate and the organic layer was dried and concentrated. The obtained residue was recrystallized from ethyl acetate to give the title compound (322 mg) as a colorless solid. 1H-NMR (CDCl3+CD3OD) δ: 0.83 (3H, d, J=6.6 Hz), 0.98 (3H, d, J=6.6 Hz), 2.52-2.76 (1H, m), 3.85 (3H, s), 6.92-7.02 (3H, m), 7.38-7.62 (7H, m). IR (KBr): 3218, 1497; 1252, 1038, 1007, 816 cm-1.

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US6518257, 2003, B1

32
[ 589-87-7 ]
[ 5720-07-0 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With caesium carbonate In water; N,N-dimethyl-formamide at 20℃; Inert atmosphere;	General procedure for Suzuki cross coupling reaction General procedure: The Suzuki coupling reactions were carried out in a test tube (13 mm) using an organic synthesizer. Aryl iodides, bromides and chlorides (0.1 mmol) base (150 mol%), arylboronic acid (0.15 mmol) and Pd catalysts 3-5 atom% were placed in a test tube. The argon gas was supplied from the balloon with argon exchange 2 times without degassing. Solvent was added and stirred at 1000 rpm at specified temperature for the desired time. Completion of the reaction was monitored by TLC. After completion, the reaction was cooled and quenched by 1M HCl, extract with EtOAc. The organic layer was evaporated, dried and the yields were reported as NMR or isolated yield after purification by silica gel column chromatography (eluted with EtOAc/Hexane). The products were confirmed by 1H NMR spectra and mass comparing with the pure, commercially available compounds and reported NMR in the literature which exactly matched with the reported values.1-18
95%	With sodium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 8h; Inert atmosphere;
84%	With potassium fluoride In toluene at 80℃; for 3.5h;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; N,N-dimethyl-formamide at 110℃; Inert atmosphere; Sealed tube;

General procedure: To a solution of 4-Methylphenylboronic acid (2.8g,21mmol) in DMF/water (v/v, 1:1) was added 1-bromo-4-iodobenzene (4g, 14mmol) , Tetrakis (triphenylphosphine)palladium (0.8g, 0.7mmol) and K2CO3 (5.8g, 42mmol), themixture was stirred at 110oC in a sealed tube under N2 over night. The reaction mixture was cooled and poured into an ice-wate rmixture solution, filtering to get solid material. The residue was purified by column chromatography on silica gel (petroleum ether) to yield the title compound

Reference： [1]Karanjit, Sangita; Kashihara, Masaya; Nakayama, Atsushi; Shrestha, Lok Kumar; Ariga, Katsuhiko; Namba, Kosuke [Tetrahedron, 2018, vol. 74, # 9, p. 948 - 954]
[2]Nikitin, Oleg M.; Polyakova, Olga V.; Sazonov, Petr K.; Yakimansky, Alexander V.; Goikhman, Mikhail Ya.; Podeshvo, Irina V.; Magdesieva, Tatiana V. [New Journal of Chemistry, 2016, vol. 40, # 12, p. 10465 - 10473]
[3]Suzuki, Ken; Fontaine, Arnaud; Hori, Yoji; Kobayashi, Tohru [Synlett, 2007, # 20, p. 3206 - 3208]
[4]Ding, Yuyang; Mao, Liufeng; Xu, Dengfeng; Xie, Hui; Yang, Ling; Xu, Hongjiang; Geng, Wenjun; Gao, Yong; Xia, Chunguang; Zhang, Xiquan; Meng, Qingyi; Wu, Donghai; Zhao, Junling; Hu, Wenhui [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 14, p. 2744 - 2748]

33
[ 232946-69-9 ]
[ 58743-83-2 ]
[ 232946-70-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With n-butyllithium In tetrahydrofuran; hexane; toluene react. of BuLi with bromide at -78°C, react. at 110°C for 16 h;

Reference： [1]Spivey, Alan C.; Diaper, Christopher M.; Rudge, Andrew J. [Chemical Communications, 1999, # 9, p. 835 - 836]

34
[ 58743-83-2 ]
[ 1134201-97-0 ]
[ 1134201-98-1 ]

Yield	Reaction Conditions	Operation in experiment
81%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 80℃;

Reference： [1]Feng, Xinliang; Pisula, Wojciech; Kudernac, Tibor; Wu, Dongqing; Zhi, Linjie; et al. [Journal of the American Chemical Society, 2009, vol. 131, p. 4439 - 4448]

35
[ 58743-83-2 ]
[ 347390-30-1 ]
4-(4'-methoxylphenyl)-4''-(3''',7'''-dimethyloctanyl)diphenylacetylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 80℃;

Reference： [1]Feng, Xinliang; Pisula, Wojciech; Kudernac, Tibor; Wu, Dongqing; Zhi, Linjie; et al. [Journal of the American Chemical Society, 2009, vol. 131, p. 4439 - 4448]

36
[ 58743-83-2 ]
[ 126708-45-0 ]
4-(4'-methoxylphenyl)-4''-dodecyldiphenylacetylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 80℃;

Reference： [1]Feng, Xinliang; Pisula, Wojciech; Kudernac, Tibor; Wu, Dongqing; Zhi, Linjie; et al. [Journal of the American Chemical Society, 2009, vol. 131, p. 4439 - 4448]

37
[ 106-37-6 ]
[ 5720-07-0 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With palladium diacetate at 20℃; for 3h; Green chemistry;
82%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In methanol; toluene for 12h; Reflux; Inert atmosphere; regiospecific reaction;	4.2.1. 4-Bromo-4'-methoxybiphenyl (4)²³ The reaction was carried out by following the reflux-12 h procedure, using p-dibromobenzene (2, 0.50 g, 2.12 mmol), 4-methoxyphenyl boronic acid (3a, 0.22 g, 1.41 mmol), cesium carbonate (0.92 g, 2.82 mmol), Pd(PPh3)4 (0.13 g, 0.11 mmol), toluene (20 mL), and methanol (10 mL). Compound 4 was isolated by column chromatography (silica gel, cyclohexane/AcOEt 8/2) as a white solid (0.31 g, 82% yield), mp: 143-145 °C; 1H NMR (400 MHz, CDCl3) δ: 7.53 (dd, 4H, J=7.6, 8.8 Hz, ArH), 7.40 (d, 2H, J=8.3 Hz, ArH), 6.97 (d, 2H, J=8.8 Hz, ArH), 3.84 (s, 3H, OCH3) ppm; MS m/z (%): 264 (M+, 0.2), 262 (0.2), 184 (100), 169 (47), 152 (5).
80%	Stage #1: 1.4-dibromobenzene With 3,3’-(pyridine-2,6-diylbis(1H-imidazole-3-ium-1,3-diyl))bis(propane-1-sulfonate); palladium diacetate; potassium carbonate In water; acetonitrile at 30℃; for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: 4-methoxyphenylboronic acid In water; acetonitrile at 20℃; for 12h; Inert atmosphere; Schlenk technique;

80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In methanol; toluene at 100℃; for 16h; Inert atmosphere;	18.A Step A: Step A: 4-bromo-4'-methoxy-1,1'-biphenyl To a solution of (4-methoxyphenyl)boronic acid (5 g, 32.9 mmol) in toluene/MeOH (200 mL/100 mL) was added 1,4-dibromobenzene (11.6 g, 49.4 mmol), Pd(PPh3)4 (1.9 g, 1.65 mmol) and Cs2CO3 (21.4 g, 65.8 mmol). The resulting solution was stirred at 100° C. for 16 hours under N2 atmosphere. TLC showed the reaction was completed. After cooled to room temperature, the reaction mixture was diluted with 50 mL of EA, washed with water, brine. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by chromatography column to afford 4-bromo-4'-methoxy-1,1'-biphenyl (7.0 g, 80% yield). LCMS (ES+): m/z 263.1 [M+H]+.
80%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate In methanol; toluene at 100℃; for 16h; Inert atmosphere;	A Step A: 4-bromo-4'-methoxy-1,1'-biphenyl To a solution of (4-methoxyphenyl)boronic acid (5 g, 32.9 mmol) in toluene/ MeOH (200 mL/100 mL) was added 1,4-dibromobenzene (11.6 g, 49.4 mmol), Pd(PPh3)4 (1.9 g, 1.65 mmol) and Cs2CO3 (21.4 g, 65.8 mmol). The resulting solution was stirred at 100 °C for 16 hours under N2 atmosphere. TLC showed the reaction was completed. After cooled to room temperature, the reaction mixture was diluted with 50 mL of EA, washed with water, brine. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by chromatography column to afford 4-bromo-4'-methoxy-1,1'-biphenyl (7.0 g, 80% yield). LCMS (ES+): m/z 263.1 [M+H]+.
69%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In toluene at 90 - 100℃; for 14h; Inert atmosphere;
67%	With potassium hydroxide In water at 60℃; for 10h;
34%	With palladium diacetate; caesium carbonate; triphenylphosphine In toluene at 110℃; for 16h; Inert atmosphere;
	Stage #1: 1.4-dibromobenzene; 4-methoxyphenylboronic acid With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran for 0.25h; Inert atmosphere; Stage #2: With sodium carbonate In tetrahydrofuran; 1,2-dimethoxyethane; water at 70℃; for 12h; Inert atmosphere;	Synthesis of 25 Under an argon atmosphere 19 (2.0 g, 13.1 mmol), 1,4-dibromobenzene (6.2 g, 26.3 mmol, 2 eq.) and Pd(PPh3)4 (0.23 g, 0.2 mmol) were dissolved in dry THF (44 mL, 0.3 M). After stirring for 15 min, a solution of Na2CO3 (5.58 g, 52.6 mmol) in H2O (14 mL, 60 eq.) was added to the reaction mixture. And then some droplets of ethylene glycol were added to the mixture and heated to 70 °C for 12 h. After cooling to room temperature, the mixture was filtered through celite using ethyl acetate. The resulting organic layer was washed with saturated aqueous solution of ammonium chloride and brine. The combined organic layers were dried over anhydrous MgSO4 and evaporated under reduced pressure. The crude product was suspended in boiling ethanol (60 mL) and filtered while being hot. (Gray filter cake was obtained). Residual filtrate was crystallized by cold EtOH.

Reference： [1]Boruah, Preeti Rekha; Ali, Abdul Aziz; Chetia, Mitali; Saikia, Bishwajit; Sarma, Diganta [Chemical Communications, 2015, vol. 51, # 57, p. 11489 - 11492]
[2]Location in patent: experimental part Guillén, Elena; Hierrezuelo, Jesús; Martínez-Mallorquín, Rocio; López-Romero, J. Manuel; Rico, Rodrigo [Tetrahedron, 2011, vol. 67, # 14, p. 2555 - 2561]
[3]Prajapati; Schulzke; Kindermann; Kapdi [RSC Advances, 2015, vol. 5, # 65, p. 53073 - 53085]
[4]Current Patent Assignee: ARVINAS; YALE UNIVERSITY - US2018/179183, 2018, A1 Location in patent: Paragraph 1606
[5]Current Patent Assignee: ARVINAS; YALE UNIVERSITY - WO2020/51564, 2020, A1 Location in patent: Paragraph 0909; 0910
[6]Moorthy, Jarugu Narasimha; Koner, Apurba L.; Samanta, Subhas; Roy, Ankur; Nau, Werner M. [Chemistry - A European Journal, 2009, vol. 15, # 17, p. 4289 - 4300]
[7]Dey, Deepa; Bhattacharya, Tamalika; Majumdar, Biju; Mandani, Sonam; Sharma, Bhagwati; Sarma, Tridib K. [Dalton Transactions, 2013, vol. 42, # 38, p. 13821 - 13825]
[8]Mills, L. Reginald; Graham, Joshua M.; Patel, Purvish; Rousseaux, Sophie A. L. [Journal of the American Chemical Society, 2019, vol. 141, # 49, p. 19257 - 19262]
[9]Kim, Nam-Kyun; Sogawa, Hiromitsu; Takata, Toshikazu [Tetrahedron Letters, 2020, vol. 61, # 23]

38
[ 58743-83-2 ]
[ 29558-77-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With boron tribromide In dichloromethane at 20℃; Cooling with ice;
90%	With boron tribromide In dichloromethane at -50 - 20℃; for 3h; Inert atmosphere;

Reference： [1]Moorthy, Jarugu Narasimha; Koner, Apurba L.; Samanta, Subhas; Roy, Ankur; Nau, Werner M. [Chemistry - A European Journal, 2009, vol. 15, # 17, p. 4289 - 4300]
[2]Sen, Choong Ping; Valiyaveettil, Suresh [RSC Advances, 2016, vol. 6, # 97, p. 95137 - 95148]

39
[ 948846-61-5 ]
[ 58743-83-2 ]
(3aR,6aR)-1-(4'-methoxy-biphenyl-4-yl)-5-methyl-octahydropyrrolo[3,4-b]pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.3%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 70℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Zhao, Chen; Sun, Minghua; Bennani, Youssef L.; Miller, Thomas R.; Witte, David G.; Esbenshade, Timothy A.; Wetter, Jill; Marsh, Kennan C.; Hancock, Arthur A.; Brioni, Jorge D.; Cowart, Marlon D. [Journal of Medicinal Chemistry, 2009, vol. 52, # 15, p. 4640 - 4649]

40
1-bromo-2-methyl-butane [ No CAS ]
[ 58743-83-2 ]
[ 341497-51-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 1-bromo-2-methyl-butane With magnesium In tetrahydrofuran at 58℃; Inert atmosphere; Stage #2: 4-bromo-4'-methoxylbiphenyl With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at 20℃; Inert atmosphere;

Reference： [1]Kim, Chunki; Marshall, Kenneth L.; Wallace, Jason U.; Chen, Shaw H. [Journal of Materials Chemistry, 2008, vol. 18, # 46, p. 5592 - 5598]

41
[ 76-09-5 ]
[ 58743-83-2 ]
2-(4'-methoxy-[1,1^,-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at 25℃; for 12h; Inert atmosphere; Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran; hexane at 25℃; for 12h;

Reference： [1]Kulhanek, Jiri; Bures, Filip; Ludwig, Miroslav [Beilstein Journal of Organic Chemistry, 2009, vol. 5]

42
[ 589-87-7 ]
[ 171364-79-7 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 80℃;

Reference： [1]Location in patent: scheme or table Kulhanek, Jiri; Bures, Filip; Ludwig, Miroslav [Beilstein Journal of Organic Chemistry, 2009, vol. 5]

43
[ 79452-83-8 ]
[ 673-40-5 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1% Pd/C In methanol at 50℃; for 0.25h; Inert atmosphere;

Reference： [1]Bonin, Helene; Delbrayelle, Dominique; Demonchaux, Patrice; Gras, Emmanuel [Chemical Communications, 2010, vol. 46, # 15, p. 2677 - 2679]

44
[ 673-40-5 ]
potassium 4-(methoxy)phenyltrifluoroborate [ No CAS ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With palladium 10% on activated carbon In methanol Reflux; Under air;

Reference： [1]Location in patent: experimental part Hanna Jr., James M.; Varnedoe, Lee S.; Angel, Brad D.; McClellan, Joshua L. [Letters in Organic Chemistry, 2010, vol. 7, # 1, p. 1 - 6]

45
[ 139139-81-4 ]
[ 100-66-3 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
58%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 72h; regioselective reaction;

Reference： [1]Ciana, Claire-Lise; Phipps, Robert J.; Brandt, Jochen R.; Meyer, Falco-Magnus; Gaunt, Matthew J. [Angewandte Chemie - International Edition, 2011, vol. 50, # 2, p. 458 - 462]

46
[ 58743-83-2 ]
[ 247174-71-6 ]
[ 337534-45-9 ]

Yield	Reaction Conditions	Operation in experiment
39%	Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 1-[1H-imidazol-4⁽⁵⁾-yl]-2-methylpropan-1-one In tetrahydrofuran; hexane at -78 - 20℃; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane	4.1. General procedure for method A and 1-[1,1'-biphenyl]-3-yl-1-(1H-imidazol-4-yl)-2-methyl-1-propanol (5) General procedure: n-BuLi in hexane (1.6 M; 6.4 mL, 10.2 mmol) was added to a cooled (-78 °C) solution of 2a (2.11 g, 9.05 mmol) in THF (30 mL) and the mixture was stirred at -78 °C for 1 h. A solution of 4 (400 mg, 2.89 mmol) in THF (10 mL) was added to the mixture and the solution was allowed to warm to rt. The reaction was quenched with aqueous NH4Cl solution and the aqueous phase was extracted with AcOEt. The extract was dried over MgSO4 and concentrated under reduced pressure. The residue was chromatographed on silica gel (CH2Cl2/MeOH = 20:1) and recrystallized from AcOEt-hexane to give 5 (450 mg, 1.54 mmol, 53%) as a colorless powder.

Reference： [1]Location in patent: experimental part Kaku, Tomohiro; Tsujimoto, Saori; Matsunaga, Nobuyuki; Tanaka, Toshimasa; Hara, Takahito; Yamaoka, Masuo; Kusaka, Masami; Tasaka, Akihiro [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 7, p. 2428 - 2442]

47
[ 104-92-7 ]
[ 5467-74-3 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate; palladium dichloride In ethanol; water at 20℃; for 0.5h;	General procedure for the Suzuki reaction of aryl bromides with arylboronic acids General procedure: A mixture of aryl bromide (0.5 mmol), arylboronic acid (0.75 mmol), PdCl2 (0.0025 mmol, 0.44 mg), K2CO3 (1 mmol) was stirred in distilled water (2 mL) and ethonal (2 mL) at room temperature in air for the indicated time. After the completion of the reaction, the mixture was quenched by brine (15 mL), extracted with diethyl ether (4×10 mL), dried by anhydrous MgSO4, concentrated under vacuum and the product was afforded by column chromatography on silica gel (200-300 mesh) eluted with petroleum ether and ethyl acetate.
94%	With potassium carbonate In ethyl acetate at 90℃; for 1.5h;
87%	With C₁₂H₁₂Cl₂N₄O₂Pd; caesium carbonate In water at 60℃; for 4h;	General procedure for the Reaction of Arylboronic Acids and Halobenzenes General procedure: In an oven dried 10 mL round bottom flask were added arylboronic acid 1 (1.0 mmol), halobenzene 2 (1.0 mmol), Cs2CO3 (0.5 equiv) and catalyst C4 (1.0 mol%) in water (1mL). The reaction mixture was allowed to stir at 60 oC for completion. After completion of reaction (monitored by TLC) the crude residue was extracted into in ethylacetate (10 mL x 3) and dried over anhydrous sodium sulphate, filtered and evaporated under reduced pressure. The crude mixture was separated using silica-gel column chromatography by eluting with ethylacetate/hexanes.

7 %Spectr.

With C₁₆H₂₈Cl₂N₄O₂Pd; potassium carbonate In methanol; carbon dioxide at 120℃; for 1h; Supercritical conditions;

Reference： [1]Qiu, Jun; Wang, Limin; Liu, Mingtao; Shen, Qiang; Tang, Jun [Tetrahedron Letters, 2011, vol. 52, # 48, p. 6489 - 6491]
[2]Han, Yi; Di, Jia-Qi; Zhao, Ai-Dong; Zhang, Zhan-Hui [Applied Organometallic Chemistry, 2019, vol. 33, # 10]
[3]Thunga, Sanjeeva; Poshala, Soumya; Anugu, Naveenkumar; Konakanchi, Ramaiah; Vanaparthi, Satheesh; Kokatla, Hari Prasad [Tetrahedron Letters, 2019, vol. 60, # 31, p. 2046 - 2048]
[4]Location in patent: experimental part Fernandes, Ricardo R.; Lasri, Jamal; DaSilva, M. Fatima C. Guedes; Palavra, Antonio M. F.; Dasilva, Jose A. L.; Dasilva, Joao J. R. Frausto; Pombeiro, Armando J. L. [Advanced Synthesis and Catalysis, 2011, vol. 353, # 7, p. 1153 - 1160]

48
[ 700-58-3 ]
[ 58743-83-2 ]
[ 1358802-88-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 4-bromo-4'-methoxylbiphenyl With iodine; magnesium In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; Stage #2: 2-Adamantanone In tetrahydrofuran at 20℃; Reflux; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water at 20℃; Inert atmosphere;
65%

Reference： [1]Location in patent: experimental part Basaric, Nikola; Cindro, Nikola; Bobinac, Damir; Mlinaric-Majerski, Kata; Uzelac, Lidija; Kralj, Marijeta; Wan, Peter [Photochemical and Photobiological Sciences, 2011, vol. 10, # 12, p. 1910 - 1925]
[2]Govender, Thavendran; Govinden, Usha; Mocktar, Chunderika; Kruger, Hendrik G.; Veljković, Jelena; Cindro, Nikola; Bobinac, Damir; Žabčić, Ivana; Mlinarić-Majerski, Kata; Basarić, Nikola [South African Journal of Chemistry, 2016, vol. 69, p. 44 - 50]

49
[ 119-61-9 ]
[ 58743-83-2 ]
[ 861097-26-9 ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: 4-bromo-4'-methoxylbiphenyl With iodine; magnesium In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; Stage #2: benzophenone In tetrahydrofuran at 20℃; Reflux; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water at 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Basaric, Nikola; Cindro, Nikola; Bobinac, Damir; Mlinaric-Majerski, Kata; Uzelac, Lidija; Kralj, Marijeta; Wan, Peter [Photochemical and Photobiological Sciences, 2011, vol. 10, # 12, p. 1910 - 1925]

50
[ 58743-83-2 ]
[ 67-64-1 ]
[ 93015-08-8 ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: 4-bromo-4'-methoxylbiphenyl With iodine; magnesium In tetrahydrofuran at 20℃; Inert atmosphere; Reflux; Stage #2: acetone In tetrahydrofuran at 20℃; Reflux; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water at 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Basaric, Nikola; Cindro, Nikola; Bobinac, Damir; Mlinaric-Majerski, Kata; Uzelac, Lidija; Kralj, Marijeta; Wan, Peter [Photochemical and Photobiological Sciences, 2011, vol. 10, # 12, p. 1910 - 1925]

51
[ 58743-83-2 ]
[ 4688-76-0 ]
[ 1427642-41-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	With 1-Hydroxymethyl-1H-benzotriazole; palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 80℃; Inert atmosphere;

Reference： [1]Jha, Rajeev R.; Singh, Jaspal; Tiwari, Rakesh K.; Verma, Akhilesh K. [ARKIVOC, 2012, vol. 2013, # 2, p. 228 - 248]

52
[ 5720-07-0 ]
[ 712299-29-1 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With palladium diacetate; potassium carbonate In methanol at 60℃; Inert atmosphere; chemoselective reaction;

Reference： [1]Liu, Jin-Biao; Yan, Hui; Chen, Hui-Xuan; Luo, Yu; Weng, Jiang; Lu, Gui [Chemical Communications, 2013, vol. 49, # 46, p. 5268 - 5270]

53
[ 5720-07-0 ]
[ 589-21-9 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With bis-triphenylphosphine-palladium(II) chloride; sodium dodecyl-sulfate; potassium carbonate; p-toluenesulfonyl chloride In water at 60℃;	Typical procedure for Pd-catalyzed Suzuki cross-coupling of arylhydrazines with aryl boronic acids General procedure: A mixture of arylhydrazine 1 (0.24mmol, 1.2equiv.), aryl boronic acid 2 (0.2 mmol), K2CO3(0.6 mmol, 3.0 equiv.), p-toluenesulfonylchloride (0.24 mmol, 1.2 equiv.), sodium dodecyl sulfate (0.02 mmol, 10 mol %), and PdCl2(PPh3)2(0.01 mmol, 5 mol %) was stirred at 60 °C in water (2.0 mL) for 4-8 h under air.After completion of the reaction (indicated by TLC), the mixture was quenched with saturatedNaCl solution, extracted by EtOAc,and dried with Na2SO4. The crude product was purified by flash columnchromatography to provide the corresponding product 3.

Reference： [1]Liu, Jin-Biao; Zhou, He-Ping; Peng, Yi-Yuan [Tetrahedron Letters, 2014, vol. 55, # 17, p. 2872 - 2875]

54
[ 4746-97-8 ]
[ 58743-83-2 ]
[ 1609571-89-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 1h; Inert atmosphere; Stage #2: cyclohexanedione monoethylene ketal In tetrahydrofuran; cyclohexane at -78 - 20℃; for 1.5h; Inert atmosphere;

Reference： [1]Garmshausen, Yves; Schwarz, Jutta; Hildebrandt, Jana; Kobin, Bjoern; Paetzel, Michael; Hecht, Stefan [Organic Letters, 2014, vol. 16, # 11, p. 2838 - 2841]

55
[ 104-92-7 ]
[ 106-37-6 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium tetrachloropalladate(II); tetrahydroxydiboron; sodium dodecyl-sulfate; tricyclohexylphosphine tetrafluoroborate; sodium hydroxide In water at 60 - 100℃; for 12h; chemoselective reaction;
59%	Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; cyclohexane at -78℃; for 2h; Inert atmosphere; Stage #2: With Triisopropyl borate In tetrahydrofuran; cyclohexane at -78 - 20℃; for 2.3h; Inert atmosphere; Stage #3: 1.4-dibromobenzene With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In tetrahydrofuran; cyclohexane; water; ethylene glycol for 17h; Inert atmosphere; Reflux;

Reference： [1]Xu, Shan Dong; Sun, Fang Zhou; Deng, Wei Hang; Hao, Han; Duan, Xin Hong [New Journal of Chemistry, 2018, vol. 42, # 20, p. 16464 - 16468]
[2]Garmshausen, Yves; Schwarz, Jutta; Hildebrandt, Jana; Kobin, Bjoern; Paetzel, Michael; Hecht, Stefan [Organic Letters, 2014, vol. 16, # 11, p. 2838 - 2841]

56
[ 108-86-1 ]
[ 5720-07-0 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate In water at 20℃; for 1h;

Reference： [1]Li, Zhi-Qiang; Zhang, Ying-Ming; Chen, Yong; Liu, Yu [Chemistry - A European Journal, 2014, vol. 20, # 28, p. 8566 - 8570]

57
[ 1642135-90-7 ]
[ 5720-07-0 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
34%	With bis-triphenylphosphine-palladium(II) chloride; oxygen; potassium carbonate In methanol at 60℃;

Reference： [1]Zhou, He-Ping; Liu, Jin-Biao; Yuan, Jian-Jun; Peng, Yi-Yuan [RSC Advances, 2014, vol. 4, # 49, p. 25576 - 25579]

58
[ 106-41-2 ]
[ 5720-07-0 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
10%	With potassium phosphate; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); 4-methyl-N-phenyl-N-tosylbenzenesulfonamide In 1,4-dioxane at 110℃; Inert atmosphere; Schlenk technique;

Reference： [1]Chen, Liangshun; Lang, Hongyue; Fang, Lei; Zhu, Mengyun; Liu, Jinqian; Yu, Jianjun; Wang, Limin [European Journal of Organic Chemistry, 2014, vol. 2014, # 23, p. 4953 - 4957]

59
[ 613-37-6 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
32 %Chromat.	With N-Bromosuccinimide; [bis(acetoxy)iodo]benzene; nickel dibromide In water-d2 at 25℃; for 24h; Sealed tube; Inert atmosphere;	2.3. Standard procedure for catalytic bromination General procedure: To 2 mL CF3COOH (or D2O), 0.25 mmol substrate, 0.5 mmol oxidizing agent, 0.375 mmol NBS and 5 mol% catalyst were added. The reagents were taken in a specially designed tube (10 mL), were purged with N2 gas, and sealed; the mixture was stirred for 24 h at room temperature. Next, the volatiles were removed under reduced pressure. The brominated products were analyzed by 1HNMR spectroscopy and the yields were calculated by GC/MS using dodecane as an internal standard.
32.0 %Chromat.	With N-Bromosuccinimide; [bis(acetoxy)iodo]benzene; nickel dibromide In water-d2 at 20℃; for 24h; Inert atmosphere; Sealed tube;

Reference： [1]Bhattacharya, Moumita; Cluff, David B.; Das, Siddhartha [Inorganica Chimica Acta, 2014, vol. 423, # 1, p. 238 - 241]
[2]Bhattacharya, Moumita; Cluff, David B.; Das, Siddhartha [Inorganica Chimica Acta, 2014, vol. 423, # PA, p. 238 - 241]

60
[ 58743-83-2 ]
2-methyl-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)benzaldehyde [ No CAS ]
C₅₅H₅₄O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 2-methyl-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)benzaldehyde In tetrahydrofuran; hexane at -78℃; for 3h;	General procedure: To a cold (-78 oC) solution of 14b (375mg,1.5mmol) in THF (25mL) was added n-BuLi(1.3M in hexane; 2.5 mL, 3 mmol) and the mixture was stirred at -78 oC for 1 h. To the reaction mixture was added a solution of 21d (640 g, 1mmol)in THF (60 mL) and the mixture was stirred at -78 oC for 3 h. To the reaction mixture was added saturated aqueous ammonium chloride solution and extracted with EtOAc, then the organic layer was separated and washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel (EtOAc-petroleum ether =1:5) to give a colorless oil.

Reference： [1]Ding, Yuyang; Mao, Liufeng; Xu, Dengfeng; Xie, Hui; Yang, Ling; Xu, Hongjiang; Geng, Wenjun; Gao, Yong; Xia, Chunguang; Zhang, Xiquan; Meng, Qingyi; Wu, Donghai; Zhao, Junling; Hu, Wenhui [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 14, p. 2744 - 2748]

61
[ 58743-83-2 ]
[ 189628-37-3 ]
(5-bromo-2-chlorophenyl)(4'-methoxy-[1, 1'-biphenyl]-4-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		General procedure: To a cold (-78 oC) solution of 4-bromo-4'-methylbiphenyl 14d (2.5g, 10mmol) in THF (25mL) was added n-BuLi (2.5M in hexane; 4 mL, 10 mmol) and the mixture was stirredat -78 oC for 1 h. To the reaction mixture was added a solution of 10c(2.34 g, 11mmol) in THF (20 mL) and the mixture was stirred at -78 oCfor 3h. To the reaction mixture was added saturated ammonium chloride solutionand EtOAc, then the organic layer was separated and washed with brine, driedover Na2SO4, filtered and evaporated in vacuo. Theresulting residue was purified by column chromatography on silica gel(EtOAc/petroleum ether = 1:10) to give the title compound.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2744 - 2748

62
4-bromophenyl 2,3,4,5,6-pentafluorobenzenesulfonate [ No CAS ]
[ 5720-07-0 ]
[ 58743-83-2 ]
[ 13021-19-7 ]
C₁₉H₁₁F₅O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate monohydrate In <i>tert</i>-butyl alcohol at 28℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube; chemoselective reaction;	4. Chemoselective Suzuki-Miyaura Cross-Coupling of ArOPFBs General procedure: To a Schlenk tube equipped with a magnetic stirring bar and a septum was charged K3PO4.H2O (3 mmol, 3 equiv), aryl pentafluorobenzene sulfonates - 1 (0.5 mmol, 1.0 equiv), aryl boronic acid (0.5 mmol, 1.0 equiv) and Pd(PPh3)2Cl2 (0.015 mmol, 3 mol%). The tube was then capped with a rubber septum, evacuated and backfilled with nitrogen and this cycle was repeated twice. Under an inert atmosphere, tert-Butanol (3 mL) was added via syringe. Under a positive pressure of nitrogen, the rubber septum was replaced with a Teflon screw cap and this was sealed. The Schlenk tube was kept on a magnetic stirrer and stirred at room temperature 12h. The reaction mixture was diluted with EtOAc (5 mL) and filtered through celite bed. The organic layer was passed through a plug of silica gel and concentrated under reduced pressure. The ratio of products formed were confirmed by GCMS (FID). The residue was then purified through silica gel (230 - 400 mesh) column chromatography using 1-5% ethyl acetate in petroleum ether to afford the product.

Reference： [1]Joseph, Jayan T.; Sajith, Ayyiliath M.; Ningegowda, Revanna C.; Nagaraj, Archana; Rangappa; Shashikanth, Sheena [Tetrahedron Letters, 2015, vol. 56, # 36, p. 5106 - 5111]

63
[ 5720-07-0 ]
[ 673-40-5 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate In methanol at 20℃; for 3h;

Reference： [1]Dubey, Abhishek V.; Kumar, A. Vijay [RSC Advances, 2016, vol. 6, # 52, p. 46864 - 46870]

64
[ 696-62-8 ]
[ 5467-74-3 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1.5h;	2.4. General procedure for Suzuki-Miyaura cross-coupling General procedure: A round bottom flask (50 mL) equipped with condenser was chargedwith aryl halide (1.0 mmol), arylboronic acid (1.2 mmol), K2CO3(2 mmol), Pd(II)-AMP-CellAl2O3 (40 mg) and dimethyl formamide(DMF) (5 mL). The mixture was stirred in an oil bath at 80 °C. Uponcompletion of the reaction as monitored by thin layer chromatography(TLC) (petroleum ether:ethyl acetate, 95:0.5), the reaction mixture wasfiltered. The filtrate was extracted with ethyl acetate (3 × 5 mL). Thecombined organic layers were collected, dried over anhydrous Na2SO4,and concentrated in vacuum to afford the crude products. These productswere purified by silica gel column chromatography (Ether /EtOAc = 9:1 v/v).
83%	With bis-triphenylphosphine-palladium(II) chloride; Aliquat 336; potassium carbonate In tetrahydrofuran; water Reflux;
76%	With sodium carbonate In water; toluene at 100℃; for 12h; Inert atmosphere;	1.1 Step 1: Synthesis of 4-bromo-4'-methoxy-1,1'-biphenyl (21): To a mixture of compound 19 (200 mg, 0.85 mmol)and compound 20 (257 mg, 1.28 mmol)in toluene- water (9: 1)(35 mL)was added Na2CO3 (181 mg, 1.70 mmol)and the reaction mixture was degassed with N2 for 20 min. PdCl2(dppf complex (60 mg, 0.08 mmol)was added and the reaction mixture was heated to 100 °C for 12 h. After completion of the reaction, the mixture was filtered through a Celite pad, filtrate was concentrated and purified by silica gel column chromatography [gradient elution with EtOAc: Hexane (10:90)] to afford compound 21 (200 mg, 76%). 1H NMR (400 MHz, CD2Cl2): d 7.51 (dd, J= 17.5, 7.0, 2.2 Hz, 4H), 7.41 (dd, J = 8.7, 2.1 Hz, 2H), 6.97 (dd, J= 8.7, 2.1 Hz, 2H), 3.85 (s, 3H).

Reference： [1]Mhaldar, Pradeep; Pore, Dattaprasad; Rashinkar, Gajanan; Vibhute, Sandip [Reactive and Functional Polymers, 2020, vol. 152]
[2]Sen, Choong Ping; Valiyaveettil, Suresh [RSC Advances, 2016, vol. 6, # 97, p. 95137 - 95148]
[3]Current Patent Assignee: SRX CARDIO LLC - WO2020/252383, 2020, A2 Location in patent: Paragraph 00232; 00248

65
[ 58743-83-2 ]
[ 1202355-37-0 ]

Reference： [1]RSC Advances,2016,vol. 6,p. 95137 - 95148

66
[ 58743-83-2 ]
potassium ferrocyanide [ No CAS ]
[ 58743-77-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 15h; Inert atmosphere;

Reference： [1]Nikitin, Oleg M.; Polyakova, Olga V.; Sazonov, Petr K.; Yakimansky, Alexander V.; Goikhman, Mikhail Ya.; Podeshvo, Irina V.; Magdesieva, Tatiana V. [New Journal of Chemistry, 2016, vol. 40, # 12, p. 10465 - 10473]

67
[ 58743-83-2 ]
[ 16881-71-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: 4-bromo-4'-methoxylbiphenyl With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: With oxaziridine In tetrahydrofuran at 0 - 25℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water Inert atmosphere;

Reference： [1]Gao, Hongyin; Zhou, Zhe; Kwon, Doo-Hyun; Coombs, James; Jones, Steven; Behnke, Nicole Erin; Ess, Daniel H.; Kürti, László [Nature Chemistry, 2017, vol. 9, # 7, p. 681 - 688]

68
[ 58743-83-2 ]
[ 1137-77-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 4-bromo-4'-methoxylbiphenyl With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: With C₁₀H₁₇NO In tetrahydrofuran; toluene at -78℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Inert atmosphere;

Reference： [1]Gao, Hongyin; Zhou, Zhe; Kwon, Doo-Hyun; Coombs, James; Jones, Steven; Behnke, Nicole Erin; Ess, Daniel H.; Kürti, László [Nature Chemistry, 2017, vol. 9, # 7, p. 681 - 688]

69
[ 121-43-7 ]
[ 58743-83-2 ]
[ 156642-03-4 ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 5℃;	18.B Step B: Step B: (4'-methoxy-[1,1'-biphenyl]-4-yl)boronic acid To a solution of 4-bromo-4'-methoxy-1,1'-biphenyl (2 g, 7.63 mmol) in dry THF (30 mL) was added n-BuLi (9.2 ml, 22.9 mmol, 2.5 M in hexane) dropwise at -78° C. under N2 atmosphere. 1 hour later, (CH3O)3B (2.38 g, 22.9 mmol) was added dropwise at -78° C. The resulting solution was stirred for 1 hour at -78° C. and overnight at 5° C. After quenched with saturated NH4Cl solution, the mixture was extracted with EA (30 mL*2.) The combined organic layer was dried over anhydrous sodium sulfate. The residue was purified by chromatography column to afford (4'-methoxy-[1,1'-biphenyl]-4-yl)boronic acid (1.0 g, 58% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.06 (s, 2H), 7.84 (d, J=7.6 Hz, 2H), 7.63 (d, J=7.6 Hz, 2H), 7.58 (d, J=7.6 Hz, 2H), 7.02 (d, J=7.6 Hz, 2H), 3.80 (s, 3H).
58%	Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at -78 - 5℃;	B Step B: (4'-methoxy-[ biphenyl]-4-yl)boronic acid To a solution of 4-bromo-4'-methoxy-1,1'-biphenyl (2 g, 7.63 mmol) in dry THF (30 mL) was added n-BuLi (9.2 ml, 22.9 mmol, 2.5 M in hexane) dropwise at -78 oC under N2 atmosphere.1 hour later, (CH3O)3B (2.38 g, 22.9 mmol) was added dropwise at -78 oC. The resulting solution was stirred for 1 hour at -78 oC and overnight at 5 °C. After quenched with saturated NH4Cl solution, the mixture was extracted with EA (30 mL x 2.) The combined organic layer was dried over anhydrous sodium sulfate. The residue was purified by (2081) chromatography column to afford (4'-methoxy-[1,1'-biphenyl]-4-yl)boronic acid (1.0 g, 58% yield). 1H NMR (400 MHz, DMSO-d6): d 8.06 (s, 2H), 7.84 (d, J = 7.6 Hz, 2H), 7.63 (d, J = 7.6 Hz, 2H), 7.58 (d, J = 7.6 Hz, 2H), 7.02 (d, J = 7.6 Hz, 2H), 3.80 (s, 3H).

Reference： [1]Current Patent Assignee: ARVINAS; YALE UNIVERSITY - US2018/179183, 2018, A1 Location in patent: Paragraph 1608
[2]Current Patent Assignee: ARVINAS; YALE UNIVERSITY - WO2020/51564, 2020, A1 Location in patent: Paragraph 0911; 0912

70
[ 58743-83-2 ]
[ 75-05-8 ]
[ 58743-77-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 1,10-Phenanthroline; hexakis(acetonitrile)nickel(II) tetrafluoroborate; 2,3,5,6-tetramethyl-1,4-bis(trimethylsilyl)-1,4-diaza-2,5-cyclo-hexadiene at 80℃; for 24h;

Reference： [1]Ueda, Yohei; Tsujimoto, Nagataka; Yurino, Taiga; Tsurugi, Hayato; Mashima, Kazushi [Chemical Science, 2019, vol. 10, # 4, p. 994 - 999]

71
[ 4482-01-3 ]
[ 5720-07-0 ]
[ 106-40-1 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: o-benzenedisulfonimide; 4-bromo-aniline With acetic acid at 0 - 5℃; for 0.166667h; Inert atmosphere; Stage #2: With isopentyl nitrite for 0.166667h; Inert atmosphere; Stage #3: 4-methoxyphenylboronic acid With bis[(trifluoromethanesulfonyl)imidate]-2-(dicyclohexyl(2’,6’-dimethoxybiphenyl))phosphine gold(I); caesium carbonate In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; chemoselective reaction;	3.19 4.3 4-Methoxybiphenyl (4a): representative procedure for the Au catalysed Suzuki-Miyaura couplings General procedure: In a oven-dried flask and under nitrogen flow, benzenediazonium o-benzenedisulfonimide (1a, 161mg, 0.5mmol) was added to a suspension of 4-methoxyphenylboronic acid (3a, 91mg, 0.6mmol), [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) (2:1) toluene adduct (39mg, 0.025mmol, 5mol%), Cs2CO3 (325mg, 1mmol) in THF (5mL). The resulting mixture was stirred at room temperature for 2h; the completion of the reaction was confirmed by the absence of azo coupling with 2-naphthol. Then, the reaction mixture was poured into diethyl ether/water (100mL, 1:1). The aqueous layer was separated and extracted with diethyl ether (50mL). The combined organic extracts were washed with water (50mL), dried with Na2SO4 and evaporated under reduced pressure. GC-MS analyses of the crude residue showed 4-methoxybiphenyl (4a), MS (EI): m/z 184 (M+) as the major product, besides traces of biphenyl, MS (EI): m/z 154 (M+), 4,4'-dimethoxybiphenyl, MS (EI): m/z 214 (M+), N-phenyl-o-benzenedisulfonimide, MS (EI): m/z 295 (M+). The crude residue was purified on a short column, eluting with petroleum ether/diethyl ether (9:1). The only isolated product was the title compound (4a, 81mg, 88% yield).

Reference： [1]Barbero, Margherita; Dughera, Stefano [Tetrahedron, 2018, vol. 74, # 39, p. 5758 - 5769]

72
[ 589-87-7 ]
[ 696-62-8 ]
[ 58743-83-2 ]
[ 92-86-4 ]
[ 2132-80-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; palladium diacetate; hydrazine hydrate In dimethyl sulfoxide; N,N-dimethyl-formamide at 20℃; for 8h; Green chemistry; Overall yield = 83 %;
	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 140℃; for 6h; Overall yield = 74 percent;	2.2. Typical procedure for the Ullmann coupling reaction General procedure: To a 15 mL reaction tube, ArI (1 mmol), (i-Pr)2NEt (2 mmol),DMF (0.5 mL) and 5 mg of PdCl2/PANI were added. The reactionmixture was stirred at 140 °C under air for 2.5 h. After the reaction,the catalyst was isolated by centrifugalization, washed by deionized water and ethanol, vacuum dried at 60 °C and then reused in the next round of reaction. Organic phase was collected, add saturatedsalt water (2 mL), extracted with ethyl acetate (15 mL), thenthe organic phase was dried with anhydrous Na2SO4. The productwas separated and purified by silica gel column chromatography(eluent: petroleum ether).

Reference： [1]Gong, Xinchi; Wu, Jie; Meng, Yunge; Zhang, Yulan; Ye, Long-Wu; Zhu, Chunyin [Green Chemistry, 2019, vol. 21, # 5, p. 995 - 999]
[2]Liang, Yanping; Liu, Wanyi; Song, Manrong; Sun, Yanyan; Wang, Gang; Wu, Zhiqiang; Zhan, Haijuan [Journal of Catalysis, 2020, vol. 384, p. 177 - 188]

73
[ 589-87-7 ]
[ 13139-86-1 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: 4-methoxyphenyl magnesium bromide With titanium(IV) tetraethanolate; phenol In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: 1,4-bromoiodobenzene With iron(III) chloride; N,N,N,N,-tetramethylethylenediamine; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran; toluene at 20 - 78℃; Inert atmosphere;

Reference： [1]Wang, Lei; Wei, Yi-Ming; Zhao, Yan; Duan, Xin-Fang [Journal of Organic Chemistry, 2019, vol. 84, # 9, p. 5176 - 5186]

74
[ 58743-83-2 ]
[ 98-80-6 ]
[ 13041-66-2 ]

Yield	Reaction Conditions	Operation in experiment
58%	With palladium diacetate; potassium carbonate In para-xylene at 150℃; for 4h; Inert atmosphere;

Reference： [1]Han, Bin; Wang, Hailong; Wang, Chiming; Wu, Hui; Zhou, Wei; Chen, Banglin; Jiang, Jianzhuang [Journal of the American Chemical Society, 2019, vol. 141, # 22, p. 8737 - 8740]

75
[ 108-86-1 ]
[ 459-64-3 ]
[ 58743-83-2 ]
[ 74447-72-6 ]
[ 74447-76-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine at 23℃; for 18h; Inert atmosphere; Irradiation; Overall yield = 82 percent; Overall yield = 129 mg;
	With copper(l) iodide; caesium carbonate at 22℃; Overall yield = 74 percent; Overall yield = 0.98 g;	4.2. Mixture of 4-methoxy-2'-methylbiphenyl; 4-methoxy-3'-methylbiphenyl; 4-methoxy-4'-methylbiphenyl (3v); typical procedure General procedure: 4-Methoxybenzenediazonium tetrafluoroborate (1a, 1.10 g, 5 mmol) was added at rt to a stirred suspension of cesium carbonate (1.63 g, 5 mmol) and copper iodide (19 mg, 0.1 mmol) in toluene (2h, 9.2 g, 100 mmol, 8 mL). Immediately, the colour of the solution turned black and slight evolution of nitrogen was observed. The mixture was stirred at room temperature for 3.5 h; the completion of the reaction was confirmed by the absence of azo coupling with 2-naphthol. Then, the reaction mixture was poured into diethyl ether/water (100 mL, 1:1). The aqueous layer was separated and extracted with diethyl ether (50 mL). The combined organic extracts were washed with water (50 mL), dried with Na2SO4 and evaporated under reduced pressure. GC-MS analyses of the crude residue showed a mixture of 4-methoxy2’-/3’/4'-methylbiphenyl (3a, MS (EI): m/z 198 [M] each) as the major products, besides traces of anisole, MS (EI) m/z 108 [M]. The crude residue (tarry solid) was purified on a short column, eluting with petroleum ether. The only isolated product was title compounds (3v, 0.71 g, 72% yield). The ratio of 4-methoxy-2'-methylbiphenyl/4-methoxy-3'-methylbiphenyl/4-methoxy-4'-methylbiphenyl was respectively 81% (retention time 11.08)/13% (retention time 11.83)/6% (retention time 11.97) and was determined by GC analysis by comparison of retention times (initial temperature: 70 °C; final temperature: 250 °C; rate 20 °C/min) with standard 2’/3’/4' regioisomers and area percent. Standard 4-methoxy-2'-methylbiphenyl, 4-methoxy-3'-methylbiphenyl, 4-methoxy-4'-methylbiphenyl were synthesized with a Pd(OAc)2 catalysed Suzuki reaction by reacting 1a respectively with 2-tolyl, 3-tolyl, 4-tolylboronic acid and they had the following retenction times (70-250 °C; rate 20 °C min): 4-methoxy-2'-methylbiphenyl 11.09 min; 4-methoxy-3'-methylbiphenyl 11.84 min; 4-methoxy-4'-methylbiphenyl 11.97 min. All other biaryls 3 and heterobiaryls 5 were prepared according to this procedure, with the exception of the reactions carried out with the solid biphenyl 2d. In this case, they were performed with 20 eq of biphenyl (15.4 g) using 10 ml of MeCN as a solvent.

Reference： [1]Lee, Juyoung; Hong, Boseok; Lee, Anna [Journal of Organic Chemistry, 2019, vol. 84, # 14, p. 9297 - 9306]
[2]Antenucci, Achille; Barbero, Margherita; Dughera, Stefano; Ghigo, Giovanni [Tetrahedron, 2020, vol. 76, # 47]

76
[ 58743-83-2 ]
[ 86164-70-7 ]
[ 58743-77-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With C₁₀H₈Br₂N₂Ni*(x)H₂O; zinc In N,N-dimethyl acetamide at 80℃; for 16h; Inert atmosphere; Sealed tube;

Reference： [1]Mills, L. Reginald; Graham, Joshua M.; Patel, Purvish; Rousseaux, Sophie A. L. [Journal of the American Chemical Society, 2019, vol. 141, # 49, p. 19257 - 19262]

77
[ 2005-10-9 ]
[ 58743-83-2 ]
6-(4'-methoxy-[1,1'-biphenyl]-4-yl)benzo[c]chromen-5-ium perchlorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: 4-bromo-4'-methoxylbiphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: 6H-benzo[c]chromen-6-one In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Inert atmosphere; Stage #3: With perchloric acid; acetic anhydride In diethyl ether; water at 0℃;	4.4. 6-(40-Methoxy-[1,10-biphenyl]-4-yl)benzo[c]chromen-5-iumperchlorate (15) 4-bromo-4'-methoxybiphenyl 6 (0.671 g, 2.55 mmol) was dissolved in 10 mL of anhydrous THF in an oven dried round bottom flask. The solution was cooled to 78 C in a dry ice/acetone bath and sparged with Ar for 45 min. 1.6 M n-BuLi in hexane (1.70 mL,2.72 mmol) was added dropwise via syringe and the reaction was stirred for 1.5 h at 78 C. During this time 6H-benzo[c]chromen-6-one 9 (0.500 g, 2.55 mmol) was dissolved in 10 mL of anhydrous THF in a separate oven dried round bottom flask. The solution was cooled to 78 C in a dry ice/acetone bath and sparged with Ar for 30 min. The aryllithium solution was transferred to the solution containing 9 at 78 C via cannula under Ar pressure. The cooling bath was removed, and the reaction was allowed to stir for 2 h. 50 mL of sat. NH4Cl was added to the reaction and subsequently extracted 3x with 25 mL of Et2O. The combined organics were dried with MgSO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in 25 mL of diethyl ether and cooled to 0 C in an ice bath and stirred very rapidly. A chilled (0 C) solution of 70% perchloric acid in acetic anhydride (1:3 by volume) was slowly added drop-wise to the stirring ethereal solution until a colored precipitate formed. The crude product was filtered and recrystallized in glacial acetic acid to yield a red-orange powder (0.508 g, 43%). mp 270e271 C. 1H NMR (400 MHz, CDCl3/CF3CO2D): d 8.90 (d, J 8.5 Hz, 1H), 8.86 (d, J 8.5 Hz, 1H), 8.76 (dd,J 8.3 Hz, J 1.5 Hz, 1H), 8.59 (t, J 7.9 Hz, 1H), 8.36 (d, J 8.5 Hz,2H), 8.27 (dd, J 8.4 Hz, J 1.1 Hz, 1H), 8.17 (t, J 8.3 Hz, 1H), 8.12(td, J 7.9 Hz, J 1.5 Hz, 1H), 8.07-8.01 (m, 3H), 7.77 (d, J 9.0 Hz,2H), 7.12 (d, J 8.8 Hz, 2H), 3.95 (s, 3H). 13C NMR (100 MHz, CDCl3/CF3CO2D): d 183.7, 160.6, 151.6, 150.2, 143.9, 139.7, 136.2, 134.9,134.3,132.1, 131.2, 131.0,129.2,128.2, 127.3, 124.1,124.0, 121.5, 120.5,119.8, 115.3, 55.9. IR (ATR) nmax: 1592, 1483, 1078 cm1. HRMS (ESI)m/z calcd for C26H19O2 [M] 363.1385, found 363.1373.

Reference： [1]Meyer, Samantha M.; Charlesworth-Seiler, Eva M.; Patrow, Joel G.; Kitzrow, Jonathan P.; Gerlach, Deidra L.; Reinheimer, Eric W.; Dahl, Bart J. [Tetrahedron, 2020, vol. 76, # 23]

78
[ 90-47-1 ]
[ 58743-83-2 ]
9-(4'-methoxy-[1,1'-biphenyl]-4-yl)xanthylium perchlorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: 4-bromo-4'-methoxylbiphenyl With magnesium; ethylene dibromide In tetrahydrofuran Reflux; Inert atmosphere; Stage #2: xanth-9-one In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Stage #3: With perchloric acid; acetic anhydride In diethyl ether; water at 0℃; for 0.5h;	4.10. 9-(40methoxy-[1,10-biphenyl]-4-yl)xanthylium perchlorate (24) Magnesium (0.132 g, 5.42 mmol) was placed into an oven-dried round bottom flask and flushed with Ar for 30 min while stirring. 4-Bromo-4'-methoxybiphenyl 6 (1.43 g, 5.42 mmol), anhydrous THF(8 mL), and 2 drops of 1,2-dibromoethane were then added. The reaction was heated to reflux, stirred for 30 min under Ar, and allowed to cool back to rt over 1 h. During this time xanthone 18 (0.532 g, 2.71 mmol) was dissolved in 16 mL of anhydrous THF in a separate oven dried round bottom flask. The flask was cooled to0 C with an ice bath and sparged for 30 min with Ar. The arylmagnesium bromide solution was transferred to the solution containing 18 at 0 C via cannula under Ar pressure. The cooling bath was removed, and the reaction was stirred for 2 h. 50 mL of sat. NaHCO3 was added to the reaction and subsequently extracted 3x with 100 mL of CH2Cl2. The combined organics were washed dried with Na2SO4, filtered, and concentrated under reduced pressure. The crude intermediate was purified via column chromatography using gradient elution (5% EtOAc in hexane/50% EtOAc in hexane) but not characterized further. The purified intermediate was dissolved in 10 mL of diethyl ether and 70% aq. HClO4 was added dropwise at rt until a colored precipitate formed. The reaction was allowed to stir for 30 min and filtered to yield a red solid. The solid was recrystallized in glacial acetic acid to yield small red needles (0.595 g, 47%). mp 230e231 C. 1H NMR (400 MHz, CDCl3/CF3CO2D): d 8.51 (ddd, J 8.6 Hz, J 7.0 Hz, J 1.2 Hz, 2H), 8.37 (d,J 8.8 Hz, 2H) 8.33 (dd, J 8.7 Hz, J 1.3 Hz, 2H), 8.01-7.94 (m, 4H),7.78 (d, J 8.1 Hz, 2H), 7.73 (d, J 8.8 Hz, 2H), 7.10 (d, J 8.8 Hz, 2H)3.94 (s, 3H). 13C NMR (100 MHz, CDCl3/CF3CO2D): d 174.9, 160.2,158.3, 145.7, 144.0, 132.0, 131.9, 131.4, 129.4, 128.7, 128.6, 127.3,123.5,120.0,114.8, 55.6. IR (ATR) nmax: 1596,1578,1083 cm1. HRMS(ESI) m/z calcd for C26H19O2 [M] 363.1385, found 363.1382.

Reference： [1]Meyer, Samantha M.; Charlesworth-Seiler, Eva M.; Patrow, Joel G.; Kitzrow, Jonathan P.; Gerlach, Deidra L.; Reinheimer, Eric W.; Dahl, Bart J. [Tetrahedron, 2020, vol. 76, # 23]

79
[ 589-87-7 ]
[ 58743-83-2 ]
[ 92-86-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: TurboGrignard / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 2.1: tetrafluoroboric acid; isopentyl nitrite / ethanol; water / 1 h / -20 - 20 °C / Inert atmosphere 2.2: 2 h / 20 °C / Inert atmosphere; Irradiation; Glovebox

Reference： [1]Dahiya, Amit; Fricke, Christoph; Funes-Ardoiz, Ignacio; Gevondian, Avetik G.; Schoenebeck, Franziska; Sherborne, Grant J. [Angewandte Chemie - International Edition, 2020, vol. 59, # 36, p. 15543 - 15548][Angew. Chem., 2020, vol. 132, # 36, p. 15673 - 15678,6]

80
[ 589-87-7 ]
[ 5720-07-0 ]
[ 58743-83-2 ]
[ 13021-19-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 14% 2: 64%	With disodium[(N,N’-bis(2-hydroxy-5-sulfonatobenzyl)-1,2-diphenyl-1,2-diaminoethano)palladate(II)]; caesium carbonate In water at 80℃; for 1h;	Catalysis experiments and gas chromatographic analysis of the reaction mixtures General procedure: Stock solutions of the catalysts (Na2[Pd(HSS)], Na2[Pd(PrHSS)], Na2[Pd(BuHSS)],Na2[Pd(dPhHSS)], rac-Na2[Pd(CyHSS)], Na2[Pd(cis-CyHSS)]) Na2[Pd(trans-CyHSS)]) were prepared by dissolving 5.0×10-7 mol complex in 6 mL water. In general, 0.5 mmol aryl-halide, 0.75 mmol boronic acid derivative (1.5 mmol in the reactions of aryl-dihalides), and 0.5 mmolbase (Cs2CO3) were used in each reaction. Good quality distilled water was used as solvent, the organic phase was comprised of the substrates. 3 mL of water was used in each reaction. The reactions were carried out at 80 °C in 30-120 min reaction time. At the end of the reactions, the mixtures were allowed to cool to room temperature and then were extracted by chlorofom (2 mL). After separation of the phases (15-20 min) the organic phase was removed by a Pasteur pipette and filtered through a short MgSO4 plug.

Reference： [1]Bunda, Szilvia; Joó, Ferenc; Kathó, Ágnes; Udvardy, Antal; Voronova, Krisztina [Molecules, 2020, vol. 25, # 17]

81
[ 106-37-6 ]
10-methyl-5-(4-methoxyphenyl)phenothiazinium hexafluorophosphate [ No CAS ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 10-methyl-5-(4-methoxyphenyl)phenothiazinium hexafluorophosphate In tetrahydrofuran; hexane at -78 - 23℃; for 1.5h; Inert atmosphere;

Reference： [1]Morofuji, Tatsuya; Yoshida, Tatsuki; Tsutsumi, Ryosuke; Yamanaka, Masahiro; Kano, Naokazu [Chemical Communications, 2020, vol. 56, # 90, p. 13995 - 13998]

82
[ 58743-83-2 ]
[ 73183-34-3 ]
2-(4'-methoxy-[1,1^,-biphenyl]-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1.4-dibromobenzene; potassium acetate In 1,4-dioxane; water at 100℃; Inert atmosphere;	1.2 Step 2: Synthesis of 2-(4'-methoxy-[l,l^,-biphenyl]-4-yl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane (22): To a mixture of compound 21 (1.0 g, 3.81 mmol), PIN2B2 (1.93 g, 7.63 mmol)in dioxane- water (9: 1)(10 mL)was added KOAc (0.748 g, 7.63 mmol)and the reaction mixture was degassed with N2 for 20 min. PdCl2(dppf complex (311 mg, 0.38 mmol)was added and the reaction mixture was heated to 100 °C for 12 h. After completion of the reaction, the solution was filtered through a Celite pad and filtrate was concentrated to afford compound 22 (1.0 g, crude).

Reference： [1]Current Patent Assignee: SRX CARDIO LLC - WO2020/252383, 2020, A2 Location in patent: Paragraph 00232; 00248-00249

83
[ 58743-83-2 ]
[ 1066-54-2 ]
[ 878131-55-6 ]

Yield	Reaction Conditions	Operation in experiment
69%	With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; water; 1,8-diazabicyclo[5.4.0]undec-7-ene In benzene at 60℃; for 24h; Inert atmosphere; Darkness;	9 Synthesis of compound 12 Add 4-bromo-4-methoxybiphenyl (2.7g, 10.12mmol), DBU (9.2g, 60.43mmol), bistriphenylphosphine palladium dichloride (425mg) into a 100mL two-necked flask, cuprous iodide (191mg), under the protection of argon, ventilate three times, add benzene 40mL, add Trimethylsilylacetylene (0.71mL), water (70ul), Heat to 60°C for 24h in the dark. After the reaction, the reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation. Add dichloromethane to disperse, filter with suction, wash the residue with water several times, methanol washed to obtain a brown crude product, after recrystallization with a large amount of toluene, compound 12 was obtained as a white solid (1.4 g, 69%).

Reference： [1]Current Patent Assignee: DONGHUA UNIVERSITY - CN109456301, 2021, B Location in patent: Paragraph 0063-0066

84
[ 67-56-1 ]
[ 398-21-0 ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
52%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoromethanesulfonate at 120℃; for 12h; Glovebox; Inert atmosphere;

Reference： [1]Kang, Qi-Kai; Li, Ke; Li, Yuntong; Lin, Yunzhi; Shi, Hang; Xu, Lun [Angewandte Chemie - International Edition, 2021, vol. 60, # 37, p. 20391 - 20399][Angew. Chem., 2021, vol. 133, # 37, p. 20554 - 20562]

85
[ 66107-30-0 ]
C₁₄H₁₄O₂Zn*MgBr*2LiCl [ No CAS ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
35%	In 2-methyltetrahydrofuran; 1-methyl-pyrrolidin-2-one; at 80℃; for 0.5h;Glovebox; Microwave irradiation; Inert atmosphere;	General procedure: In a glovebox, (het)arylpivalate 1 (0.2 mmol) and NMP (1.5 mL) were added to thediarylzinc 2 (0.3 mmol, prepared by mixing zinc bromide, lithium chloride, and the corresponding aryl magnesium bromidein 1.5 mL of THF) in a reaction tube. The reaction mixturewas then heated at 80 C for 0.5 h under MW irradiation.After completion of the reaction, the mixture was concentratedunder vacuum, and saturated NH4Cl added. The mixturewas extracted with CH2Cl2 several times. The combinedorganic layers were dried over anhydrous MgSO4, concentratedin vacuo, and the residue was purified by column chromatographyon silica gel to give the coupling product 3.

Reference： [1]Journal of Chemical Research,2021,vol. 45,p. 869 - 875

86
[ 106-37-6 ]
10-methyl-5-(4-methoxyphenyl)phenothiazinium tetrafluoroborate [ No CAS ]
[ 58743-83-2 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 1.4-dibromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 10-methyl-5-(4-methoxyphenyl)phenothiazinium tetrafluoroborate In tetrahydrofuran; hexane at -78 - 23℃; for 1.5h; Inert atmosphere;

Reference： [1]Yoshida, Tatsuki; Honda, Yuki; Morofuji, Tatsuya; Kano, Naokazu [Organic Letters, 2021, vol. 23, # 24, p. 9664 - 9668]

87
[ 108-05-4 ]
[ 58743-83-2 ]
[ 2782-23-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); lithium iodide; zinc at 65℃; for 8h; Inert atmosphere; Sealed tube; Green chemistry;

Reference： [1]Su, Mincong; Huang, Xia; Lei, Chuanhu; Jin, Jian [Organic Letters, 2022, vol. 24, # 1, p. 354 - 358]

88
[ 58743-83-2 ]
[ 125163-12-4 ]
N-(4-fluoro-5-methoxy-2-nitrophenyl)-4'-methoxy[1,1'-biphenyl]-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium tertiary butoxide; dicyclohexyl[2’,4’,6’-tris(propan-2-yl)[1,1’-biphenyl]-2-yl]phosphane In toluene at 100℃; for 16h;	9.1 Step 1: N-(4-Fluoro-5-methoxy-2-nitrophenyl)-4'-methoxy-[1,1'-biphenyl]-4-amine. A mixture of 4-fluoro-5-methoxy-2-nitroaniline (155 mg, 0.84 mmol), 1-bromo-4-(4-methoxyphenyl)benzene (200 mg, 0.76 mmol), tris(dibenzylideneacetone)dipalladium(0) (35 mg, 0.04 mmol), XPhos (36 mg, 0.08 mmol), sodium tert-butoxide (146 mg, 1.52 mmol), and toluene (2 mL) was degassed with 2 vacuum/N2 cycles, stirred at 100 °C for 16 h, and then allowed to cool to rt. The mixture was diluted with EtOAc (15 mL) and water (10 mL). Celite was added, and the mixture was filtered through Celite. The filter cake was washed with EtOAc (10 mL). The organic layer was washed with brine (10 mL), dried (Na2SO4), filtered, concentrated, and then purified by silica gel chromatography (0-15% EtOAc in hexanes) to give N-(4-fluoro-5-methoxy-2-nitrophenyl)-4'-methoxy-[1,1'-biphenyl]-4-amine (73 mg, 26%) as an orange solid. 1H NMR (400 MHz, DMSO-d6): δ 9.74 (s, 1H), 8.02 (d, J = 11.9 Hz, 1H), 7.67 (m, 4H), 7.48 (d, J = 8.6 Hz, 2H), 7.04 (d, J = 8.8 Hz, 2H), 6.85 (d, J = 7.8 Hz, 1H), 3.83-3.81 (m, 3H), 3.81-3.80 (m, 3H); LCMS: 369.2 [M+H]+.
26%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium tertiary butoxide; dicyclohexyl[2’,4’,6’-tris(propan-2-yl)[1,1’-biphenyl]-2-yl]phosphane In toluene at 100℃; for 16h;	9.1 Step 1: N-(4-Fluoro-5-methoxy-2-nitrophenyl)-4'-methoxy-[1,1'-biphenyl]-4-amine. A mixture of 4-fluoro-5-methoxy-2-nitroaniline (155 mg, 0.84 mmol), 1-bromo-4-(4-methoxyphenyl)benzene (200 mg, 0.76 mmol), tris(dibenzylideneacetone)dipalladium(0) (35 mg, 0.04 mmol), XPhos (36 mg, 0.08 mmol), sodium tert-butoxide (146 mg, 1.52 mmol), and toluene (2 mL) was degassed with 2 vacuum/N2 cycles, stirred at 100 °C for 16 h, and then allowed to cool to rt. The mixture was diluted with EtOAc (15 mL) and water (10 mL). Celite was added, and the mixture was filtered through Celite. The filter cake was washed with EtOAc (10 mL). The organic layer was washed with brine (10 mL), dried (Na2SO4), filtered, concentrated, and then purified by silica gel chromatography (0-15% EtOAc in hexanes) to give N-(4-fluoro-5-methoxy-2-nitrophenyl)-4'-methoxy-[1,1'-biphenyl]-4-amine (73 mg, 26%) as an orange solid. 1H NMR (400 MHz, DMSO-d6): δ 9.74 (s, 1H), 8.02 (d, J = 11.9 Hz, 1H), 7.67 (m, 4H), 7.48 (d, J = 8.6 Hz, 2H), 7.04 (d, J = 8.8 Hz, 2H), 6.85 (d, J = 7.8 Hz, 1H), 3.83-3.81 (m, 3H), 3.81-3.80 (m, 3H); LCMS: 369.2 [M+H]+.

Reference： [1]Current Patent Assignee: METACRINE INC - WO2022/72491, 2022, A1 Location in patent: Paragraph 00417
[2]Current Patent Assignee: METACRINE INC - WO2022/72491, 2022, A1 Location in patent: Paragraph 00417

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	58743-83-2	MDL No. :	MFCD00671954
Formula :	C₁₃H₁₁BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CMYZTJCWFRFRIW-UHFFFAOYSA-N
M.W :	263.13	Pubchem ID :	4034005
Synonyms :

Num. heavy atoms :	15
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.08
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	66.07
TPSA :	9.23 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) :	-4.36 cm/s

Log Po/w (iLOGP) :	2.94
Log Po/w (XLOGP3) :	5.0
Log Po/w (WLOGP) :	4.12
Log Po/w (MLOGP) :	4.01
Log Po/w (SILICOS-IT) :	4.2
Consensus Log Po/w :	4.05

[ CAS No. 58743-83-2 ] {[proInfo.proName]}

Quality Control of [ 58743-83-2 ]

Related Doc. of [ 58743-83-2 ]

Product Details of [ 58743-83-2 ]

Calculated chemistry of [ 58743-83-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 58743-83-2 ]

Application In Synthesis of [ 58743-83-2 ]

[ 58743-83-2 ] Synthesis Path-Upstream 1~2

[ 58743-83-2 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 58743-83-2 ]

Aryls

Bromides

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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

Log S (ESOL) :	-5.08
Solubility :	0.00218 mg/ml ; 0.00000829 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.93
Solubility :	0.00307 mg/ml ; 0.0000117 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.9
Solubility :	0.000334 mg/ml ; 0.00000127 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.5

Signal Word:	Warning	Class:
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

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P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 58743-83-2 ] {[proInfo.proName]}

Quality Control of [ 58743-83-2 ]

Related Doc. of [ 58743-83-2 ]

Product Details of [ 58743-83-2 ]

Calculated chemistry of [ 58743-83-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 58743-83-2 ]

Application In Synthesis of [ 58743-83-2 ]

[ 58743-83-2 ] Synthesis Path-Upstream 1~2

[ 58743-83-2 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 58743-83-2 ]

Aryls

Bromides

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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[ 58743-83-2 ]