[ CAS No. 3900-89-8 ] {[proInfo.proName]}

Name: 3900-89-8|(2-Chlorophenyl)boronic acid|97%
Brand: Ambeed
SKU: A408352
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2D 3D

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Quality Control of [ 3900-89-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 3900-89-8 ]

Product Details of [ 3900-89-8 ]

CAS No. :	3900-89-8	MDL No. :	MFCD00674012
Formula :	C₆H₆BClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RRCMGJCFMJBHQC-UHFFFAOYSA-N
M.W :	156.37	Pubchem ID :	2734322
Synonyms :

Calculated chemistry of [ 3900-89-8 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	41.28
TPSA :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.45
Log Po/w (WLOGP) :	0.02
Log Po/w (MLOGP) :	0.88
Log Po/w (SILICOS-IT) :	-0.08
Consensus Log Po/w :	0.45

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.1
Solubility :	1.24 mg/ml ; 0.00792 mol/l
Class :	Soluble
Log S (Ali) :	-1.91
Solubility :	1.94 mg/ml ; 0.0124 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.89
Solubility :	2.01 mg/ml ; 0.0129 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.81

Safety of [ 3900-89-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3900-89-8 ]

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

Upstream synthesis route of [ 3900-89-8 ]
Downstream synthetic route of [ 3900-89-8 ]

[ 3900-89-8 ] Synthesis Path-Upstream 1~12

1
[ 3900-89-8 ]
[ 611-33-6 ]

Reference： [1] Chinese Chemical Letters, 2014, vol. 25, # 5, p. 779 - 782

2
[ 5922-60-1 ]
[ 3900-89-8 ]
[ 2958-36-3 ]

Reference： [1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 41, p. 8204 - 8211

3
[ 3900-89-8 ]
[ 2905-23-9 ]

Reference： [1] Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10638 - 10641

4
[ 694-80-4 ]
[ 3900-89-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane; toluene at -70℃; for 1.5 h; Inert atmosphere	Procedure (f):n-BuLi (2.5 M in n-Hexane, 2.5 ml, 1.2 eq., 6.3 mmol) was added dropwise to a solution of Bromo chloro benzene (I) (ig, 0.6 ml, 5.2 mmol) and Triisopropylborate (1.44 ml, 1.2 eq., 6.27 mmol) in Toluene and THF (4:1, 10 ml)under nitrogen at -7 0°C over 1 hour. The reaction mixture was stirred for an additional 0.5 hour while the temperature was held at -70°C. The reaction mixture was allowed to warm to -20°C, before a 2 N HC1 solution (5 ml) was added to the reaction mixture. When the reaction mixture reached room temperature, it was extracted with Dichloromethane. Combined organic phase was dried and evaporatedto give a white solid, which was recrystallized from MeCN with a yield of 98percent (800mg).
56%	Stage #1: With n-butyllithium In tetrahydrofuran; hexaneInert atmosphere Stage #2: With Trimethyl borate In tetrahydrofuran; hexaneInert atmosphere	General procedure: Under an argon atmosphere a solution of the appropriate bromobenzene (1 equivalent) dissolved in anhydrous THF (approximately 30 mL per mmol bromobenzene) is cooled to -78 °C using a nitrogen-ethanol-bath. A solution of 2.3 equivalents of n-butyllithium in hexane is added drop wise keeping the temperature below -78 °C. After completion the mixture is stirred for one hour at this temperature. Then 1.5 equivalents of trimethyl borate are added slowly and the reaction mixture is stirred at -78 °C for another hour. The cooling bath is then removed, the reaction mixture is stirred until room temperature is reached and quenched with a saturated solution of ammonium chloride. THF and the major part of the water is removed under reduced pressure, the residue is laced with 3M hydrochloric acid until a pH of 3 is reached. After extraction with DCM (3 x) the organic phases are collected, washed with brine, dried over sodium sulphate and filtered. DCM is removed under reduced pressure, the resulting solid is washed first with ice cold water and then with PE and dried.

Reference： [1] Patent: WO2013/90725, 2013, A1, . Location in patent: Page/Page column 68
[2] European Journal of Medicinal Chemistry, 2017, vol. 126, p. 590 - 603
[3] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5394 - 5397

5
[ 694-80-4 ]
[ 3900-89-8 ]

Yield	Reaction Conditions	Operation in experiment
86%	With magnesium In water	A. 2-Chlorobenzeneboronic acid Borane-THF (100 mL, 100 mmol) was slowly added to a mixture of 2-bromochlorobenzene (5.4 mL, 46 mmol) and magnesium (ribbon, 1.12 g, 46 mmol). The flask was placed in a water bath and sonicated overnight. Water (30 mL) was slowly added to destroy excess borane. The aqueous solution was refluxed for 2 hrs. The solvent was evaporated and the residue was neutralized with aq HCl. The aqueous solution was extracted with ether (2*50 mL), dried (Na₂ SO₄) and evaporated to afford Compound A (6.24 g, 86percent).

Reference： [1] Patent: US6011029, 2000, A,

6
[ 870195-94-1 ]
[ 3900-89-8 ]

Reference： [1] Tetrahedron Letters, 2005, vol. 46, # 46, p. 7899 - 7903

7
[ 36692-27-0 ]
[ 688-74-4 ]
[ 3900-89-8 ]

Reference： [1] Journal of the American Chemical Society, 1934, vol. 56, p. 937,938, 941

8
[ 121-43-7 ]
[ 694-80-4 ]
[ 3900-89-8 ]

Reference： [1] Chemistry - A European Journal, 2017, vol. 23, # 9, p. 2005 - 2009

9
[ 13675-18-8 ]
[ 615-41-8 ]
[ 3900-89-8 ]

Reference： [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851

10
[ 36692-27-0 ]
[ 13195-76-1 ]
[ 3900-89-8 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1930, vol. <2>128, p. 153,169,170

11
[ 103-82-2 ]
[ 3900-89-8 ]
[ 79422-00-7 ]

Reference： [1] Chemical Science, 2018, vol. 9, # 4, p. 1058 - 1072

12
[ 76-09-5 ]
[ 3900-89-8 ]
[ 870195-94-1 ]

Reference： [1] Organic Letters, 2013, vol. 15, # 11, p. 2806 - 2809
[2] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851

[ 3900-89-8 ] Synthesis Path-Downstream 1~88

1
[ 53848-17-2 ]
[ 3900-89-8 ]
2'-chloro-3-methyl-[1,1'-biphenyl]-2-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1779 - 1782

2
[ 3900-89-8 ]
[ 360575-29-7 ]
[ 861218-16-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2998 - 3001

3
[ 3900-89-8 ]
[ 21190-88-5 ]
[ 855300-98-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2481 - 2486

4
[ 870195-94-1 ]
[ 3900-89-8 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 7899 - 7903

5
[ 3900-89-8 ]
[ 21440-97-1 ]
[ 304854-37-3 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 7 6-(2-Chloro-phenyl)4,4-dimethyl-1,4-dihydro-benzo [d] [1,3] oxazin-2-one Prepared according to Procedure A from <strong>[21440-97-1]6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one</strong> and 2-chlorophenyl boronic acid. White solid: mp 181-182 C.; MS (ESI) m/z 288 ([M+H]+, 70%); Anal. Calc. For C16H14CINO2: C, 66.79 H, 4.90, N, 4.87. Found: C, 66.78, H, 4.82, N, 4.55
		EXAMPLE 7 6-(2-Chloro-phenyl)-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one Prepared according to Procedure A from <strong>[21440-97-1]6-bromo-4,4-dimethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one</strong> and 2-chlorophenyl boronic acid. White solid: mp 181-182 C.; MS (ESI) m/z 288 ([M+H]+, 70%); Anal. Calc. For C16H14CINO2: C, 66.79, H, 4.90, N, 4.87. Found: C, 66.78, H, 4.82, N, 4.55

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4379 - 4382
[2]Patent: US2002/49204,2002,A1
[3]Patent: US6444668,2002,B1

6
[ 1666-13-3 ]
[ 3900-89-8 ]
2-chlorophenyl phenyl selenide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With C28H20CuN4O2; In dimethyl sulfoxide; at 100℃; for 10h;Green chemistry;	General procedure: The catalytic activity of the synthesized metal complexes wasevaluated for the coupling of diphenyldiselenide with phenylboronicacid as a model reaction (Scheme 1). In a typical catalysts screeningstudy, the reaction was carried out at 100 °C in dimethylsulfoxide(DMSO) solvent. The progress of reaction was monitored by GasChromatography.

Reference： [1]Molecular catalysis,2018,vol. 450,p. 14 - 18
[2]Tetrahedron Letters,2009,vol. 50,p. 6635 - 6638
[3]Journal of Organic Chemistry,2007,vol. 72,p. 1241 - 1245
[4]Green Chemistry,2012,vol. 14,p. 1030 - 1034
[5]Journal of Organic Chemistry,2016,vol. 81,p. 11472 - 11476

7
[ 63525-48-4 ]
[ 3900-89-8 ]
[ 705289-87-8 ]

Reference： [1]Journal of Materials Chemistry,2006,vol. 16,p. 4058 - 4064

8
[ 955372-88-0 ]
[ 3900-89-8 ]
[ 955372-89-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In 1,4-dioxane; water; at 100℃;	Intermediate 9: 3-(2-Chloro-phenyl)-5-(2-fluoro-phenviamino)-isonicotinic acid methyl ester; 3-Bromo-5-(2-fluoro-phenylamino)-isonicotinic acid methyl ester (250 mg, 0.77 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (0.18 g, 1.2 mmol), Pd(OAc)2 (10 mg, 0.025 mmol), S-Phos (20 mg, 0.05 mmol), and K2CO3 (0.32 g, 2.3 mmol) were suspended in dioxane / H2O (1.65 mL, 9 / 1 , v / v) and stirred overnight at 100 0C. The reaction solution was diluted with EtOAc, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude product was purified via Biotage eluting with a gradient of 0 to 50 percent EtOAc in hexanes to afford the desired product (220 mg, 80 percent) as a yellow oil. LC-MS (M+H = 357, obsd. = 357).

Reference： [1]Patent: WO2007/123936,2007,A1 .Location in patent: Page/Page column 69

9
[ 907948-61-2 ]
[ 3900-89-8 ]
[ 907948-62-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; ethanol; water; at 80℃;	Ethyl 5-bromo-2-[({4-[(4-fluorobenzyl)oxy]phenyl}acetyl)amino]indan-2-carboxylate (316 mg, 0.60 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (113 mg, 0.72 mmol), tetrakis triphenylphosphine palladium (27 mg), 2 M sodium carbonate aqueous solution (600 muL), dimethoxyethane (2 mL) and ethanol (300 muL) were stirred overnight at 80°C in an argon gas atmosphere. The reaction solution was filtered, and the filtrate was diluted with ethyl acetate and washed twice with saturated sodium bicarbonate solution and once with saturated sodium chloride solution. The organic layer was dried by addition of anhydrous magnesium sulfate The drying agent was filtered out, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluate: ethyl acetate/hexane = 2/98-1/1) and recrystallized from a mixed ethyl acetate-hexane solvent to obtain ethyl 5-(2-chlorophenyl)-2-[({4-[4-fluorobenzyl)oxy]phenyl}acetyl)amino]indan-2-carboxylate (219 mg, 65percent) as a white solid. LC-MS 558 [M+H]+ 1H-NMR (300MHz, CDCl3); delta1.19-1.24 (t, J=7.2Hz, 3H), 3.21-3.27 (d, J=16.8Hz, 2H), 3.49 (s, 2H), 3.64-3.70 (d, J=16.8Hz, 2H), 4.16-4.23 (q, J=7.2Hz, 3H), 5.00 (s, 2H), 5.97 (s, 1H), 6.89-6.92 (d, J=8.7Hz, 2H), 6.89-6.93 (m, 2H), 7.15-7.17 (d, J=8.7Hz, 2H), 7.21-7.33 (m, 6H), 7.37-7.47 (m, 3H)

Reference： [1]Patent: EP1849465,2007,A1 .Location in patent: Page/Page column 140

10
[ 201230-82-2 ]
[ 3900-89-8 ]
[ 2170-06-1 ]
[ 150192-43-1 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 5766 - 5771

11
[ 1942-45-6 ]
[ 201230-82-2 ]
[ 3900-89-8 ]
2,3-dipropyl-1H-inden-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 5766 - 5771

12
[ 935223-82-8 ]
[ 201230-82-2 ]
[ 3900-89-8 ]
3-(2-bromo-4-methylphenyl)-2-trimethylsilylinden-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 5766 - 5771

13
[ 3900-89-8 ]
[ 623-49-4 ]
[ 62123-75-5 ]

Reference： [1]Chemical Communications,2007,p. 2855 - 2857

14
[ 101066-87-9 ]
[ 3900-89-8 ]
C₁₄H₇ClF₃N [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5529 - 5532

15
[ 868265-66-1 ]
[ 3900-89-8 ]
[ 868262-23-1 ]

Yield	Reaction Conditions	Operation in experiment
75%		Treat a stirring mixture of potassium fluoride (6.6 eq), palladium acetate (0.20 eq) and 2-(dicyclohexylphosphino)-2'-methylbiphenyl (0.24 eq) in tetrahydrofuran (2 mL) at room temperature with a solution of <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (1.2 eq) in tetrahydrofuran (0.5 mL). After 15 min, add a stock solution of [2-(3-iodobiphenyl-4- yloxy)ethyl]-methylamino)acetic acid tert-butyl ester (180 mg, 0.43 mmol, 1 eq) in tetrahydrofuran. Heat the reaction to 65 °C overnight in a GreenhouseNo. reaction vessel containing consisting of 24 tubes each with a total volume of about 3 mL of solvent. Add extra potassium fluoride (2 eq), palladium acetate (0.06 eq), 2-(dicyclohexylphosphino)- 2'-methylbiphenyl (0.07 eq), and <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (1 eq) and heat the reaction mixture for a further 24 h. Allow the reactions to cool to room temperature. Filter the inorganics through a Whatman Filtertube (5mum), and further wash with tetrahydrofuran (2 x 1 mL). Evaporate the solvent in a Reacti-ThermNo. under a stream of nitrogen with heat, take up the residue in methanol, load onto an ion exchange column, wash with methanol and elute with 2 M ammonia in methanol. Evaporate solvent in a Reacti- ThermNo. under a stream of nitrogen with heat to give the title compound (145 mg, 75percent). LC-MS: m/z = 454

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5233 - 5238
[2]Patent: WO2005/100301,2005,A1 .Location in patent: Page/Page column 50-51

16
[ 529-28-2 ]
[ 3900-89-8 ]
[ 868266-04-0 ]

Yield	Reaction Conditions	Operation in experiment
96%		Stir a mixture of 2-(dicyclohexylphosphino)-2-2'-methylbiphenyl (1.49 g, 4.10 mmol), palladium acetate (765.7 mg, 3.42 mmol), potassium fluoride (6.5 g, 112.8 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (189.5 mg, 1.55 mmol) in anhydrous 1,4-dioxane for 15 min, and add 2-iodoanisole (4 g, 17.1 mmol). Heat to 110 °C overnight under nitrogen. Add extra equivalents of 2-(dicyclohexylphosphino)-2-2'-methylbiphenyl (4 g, 2.05 mmol), palladium acetate (382.9 mg, 1.71 mmol), potassium fluoride (3.25 g, 56.1 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (1.6 g, 10.3 mmol) in anhydrous 1,4-dioxane, and heat to 70 °C overnight under nitrogen. Add extra equivalents of palladium acetate (382.9 mg, 1.71 mmol), potassium fluoride (3.25 g, 56.1 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (1.6 g, 10.3 mmol) in anhydrous 1,4-dioxane, and heat to 110 °C for 3 days under nitrogen. Cool to room temperature, filter inorganics, concentrate and purify (Isco automated chromatography, eluting with 0:100 to 15: 85 ethyl acetate:cyclohexane) to give the title compound as a black oil (3.595 g, 96percent). GC-MS: 218

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5233 - 5238
[2]Patent: WO2005/100301,2005,A1 .Location in patent: Page/Page column 85-86

17
[ 227802-38-2 ]
[ 3900-89-8 ]
5-Chloro-2-(2-chlorophenyl)benzo[b]thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In Dimethyl ether; water; at 100℃;	To a solution of 1.03 g (4.16 mmol) 2-bromo-5-chlorobenzothiophene in 12 ml DME under argon were added 1.0 g (6.4 mmol) 2-chlorobenzeneboronic acid, 88 mg Pd(PPh3)4, and 6.4 ml 1M aqueous sodium carbonate solution, and the mixture was heated overnight at 100° C. in a sealed tube. After cooling 20 ml water and 20 ml ethyl acetate were added followed by vigorous stirring. The organic layer was dried over sodium sulfate and concentrated in vacuo, and the title compound was purified by chromatography on silica gel with hexane/ethyl acetate 97:3 to give 1.1 g (95percent) of a colorless oil, which slowly solidified; MS 278 (M+).

Reference： [1]Patent: US2004/9976,2004,A1 .Location in patent: Page/Page column 23
[2]Patent: EP1266897,2002,A2 .Location in patent: Page 37

18
[ 551920-28-6 ]
[ 3900-89-8 ]
[ 551920-29-7 ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In DMF (N,N-dimethyl-formamide); water; at 100℃; for 12h;	To a solution of [3- [2- (CYCLOPROPYLAMINO)-4-PYRIMIDINYL] PYRAZOLO] [1,5-b] pyridazin-6-yl [TRIFLUOROMETHANESULFONATE] (21.0 mg, 0.08 [MMOL)] in DMF (1 mL) was added Pd (PPh3) 2CI2 [(5] mg, 0.007 [MMOL),] 2-chlorophenyl boronic acid (15 mg, 0.096 [MMOL),] and [NA2CO3] (21.0 mg in 0.5 mL water). The reaction mixture was heated at an oil bath temperature of [100 °C] for about 12 hours. The mixture was cooled to RT and water (20 mL) was added. The aqueous layer was washed with EtOAc [(3X50] mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo and purified by silica-gel column chromatography (30percent EtOAc/hexanes) to give the title compound as a brown solid (15 mg, 55percent). 1H-NMR (300 MHz, [CDCI3)] [8] 9.14 (d, [1H,] J = 9.2 Hz), 8.52 (s, [1H),] 8.32 (d, [1H,] J = 5.3 Hz), 7.74-7. 71 (m, [1H),] 7.56-7. 52 (m, 2H), 7.46-7. 42 (m, 2H), 5.61 (bs, 1H), 2.88 (m, 1H), 0.89 (m, 2H), 0.66 (m, 2H); MS [(ESI)] (M+H) [+] 363.

Reference： [1]Patent: WO2004/35588,2004,A1 .Location in patent: Page 64

19
[ 685866-86-8 ]
[ 3900-89-8 ]
[ 685866-88-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium phenolate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 60℃; for 1h;Heating / reflux;	[00399] To (2-CHLORO-6-IODO-QUINAZOLIN-4-YL)- (5-CYCLOPROPYL-2H-PYRAZOL-3-YL)-AMINE (100MG, 0. 243MMOL) and 2-chlorophenyl boronic acid (57mg, 0. 364MMOL) in DMSO (5ML, purged with Ar) was added 1.5M potassium phenolate solution (648 P, L, 0.97mmol) and 1, LAPOS;BIS (diphenylphosphino) ferrocene palladium chloride, complex with dichloromethane (27mg) and the solution was heated to 60 C in a sealed tube. After LHR, solution was poured into sat. NAHC03 resulting in a yellow solid that was colleted by filtration. Flash chromatography (1-4percent methanol in dichloromethane) to give: 73mg (63percent yield). LCMS M/E : 396.2 (M+H), 394.2 (M-H)

Reference： [1]Patent: WO2004/37814,2004,A1 .Location in patent: Page 183; 185-186

20
[ 3900-89-8 ]
[ 74840-38-3 ]
[ 311335-75-8 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine;palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 105℃; for 4.0h;	a) 5-(2-Chloro-phenyl)-2-methylsulfanyl-pyrimidine-4-carboxylic acid ethyl ester To a solution of 3.20 g (11.55 mmol) <strong>[74840-38-3]5-bromo-2-methylsulfanyl-pyrimidine-4-carboxylic acid ethyl ester</strong> in 40 ml N,N-dimethylformamid 2.70 g (17.32 mmol) 2-chloro-phenyl-boronic acid, 4.82 ml (34.64 mmol) triethylamin, 0.077 g (0.35 mmol) palladium(II)acetate and 0.167 g (0.72 mmol) triphenylphosphin were added and the resulting reaction mixture heated for 4 hrs. at 105.. The reaction mixture was evaporated and the residue dissolved in 100 ml CH2Cl2.. The organic phase was washed with 80 ml 0.5 N NaOH-Solution, 80 ml H2O and 80 ml brine.. The organic phase was dried (MgSO4), filtered and evaporated.. The residue was purified by chromatography (SiO2, CH2Cl2) to give 3.00 g (84%) 5-(2-chloro-phenyl)-2-methylsulfanyl-pyrimidine-4-carboxylic acid ethyl ester a as pale brown oil.

Reference： [1]Patent: US6756380,2004,B1 .Location in patent: Page column 20

21
[ 311335-77-0 ]
[ 3900-89-8 ]
[ 311335-79-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine;palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 105℃; for 4h;	b) 5-(2-Chloro-phenyl)-2-hydroxymethyl-pyrimidine-4-carboxylic acid ethyl ester To a solution of 3.70 g (14.17 mmol) 5-bromo-2-hydroxymethyl-pyrimidine-4-carboxylic acid ethyl ester in 50 ml N,N-dimethylformamide 3.32 g (21.6 mmol) 2-chloro-phenyl-boronic acid, 5.92 ml (42.52 mmol) triethylamine, 0.095 g (0.43 mmol) palladium(II)acetate and 0.223 g (0.85 mmol) triphenylphosphine were added and the resulting reaction mixture heated for 4 hrs. at 105°.. The reaction mixture was evaporated and the residue dissolved in 100 ml CH2Cl2.. The organic phase was washed with 80 ml 0.5 N NaOH-Solution, 80 ml H2O and 80 ml brine.. The organic phase was dried (MgSO4), filtered and evaporated.. The residue was purified by chromatography (SiO2, CH2Cl2/ethyl acetate) to give 3.40 g (82percent) 5-(2-chloro-phenyl)-2-hydroxymethyl-pyrimidine-4-carboxylic acid ethyl ester a as pale brown oil.

Reference： [1]Patent: US6756380,2004,B1 .Location in patent: Page column 30-31

22
[ 619-42-1 ]
[ 3900-89-8 ]
[ 89900-96-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;palladium diacetate; triphenylphosphine; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 1h;	Combine methyl-4-bromobenzoate (1.0 g, 4.65 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (799 mg, 5.1 mmol), Pd (OAC) 2 (51 mg, 0.46 mmol) and sodium carbonate (1.5 g, 13.9 mmol) in DMF (20 mL) and water (2.0 mL) with stirring. Purge the reaction mixture with argon, add triphenylphosphine (61 mg, 0.23 mmol) and purge again with argon. Place the sealed reaction in an oil bath maintained at 80 C and allow to stir for 1 hour. Cool the reaction to room temperature, dilute with ethyl acetate and filter through a short plug of celite with additional ethyl acetate. Wash the organics with water, dry over MGS04, filter and evaporate. Purification by flash column chromatography yields 2'- chlorobiphenyl-4-carboxylic acid methyl ester as a yellow solid. Dissolve the purified ester in THF (0.25M) and add an equal volume of 1 M NAOH. Stir vigorously at room temperature for 15 hours. Upon completion, acidify the reaction with conc. HCI and extract with ethyl acetate. Evaporation of the solvent yields 762 mg (67%) of the title compound. MS (ES): M/Z 231. 1 (M-H).
	With sodium carbonate;palladium diacetate; triphenylphosphine; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 1h;	Combine methyl-4-bromobenzoate (1.0 g, 4.65 mmol), 2-CHLOROPHENYLBORONIC acid (799 mg, 5.1 mmol), Pd (OAc) 2 (51 mg, 0.46 mmol) and sodium carbonate (1.5 g, 13.9 mmol) in dimethylformamide (20 mL) and water (2.0 mL) with stirring. Purge the reaction mixture with argon, add triphenylphosphine (61 mg, 0.23 mmol) and purge again with argon. Place the sealed reaction in an oil bath maintained at 80C and allow'to stir for 1 hour. Cool the reaction to room temperature, dilute with ethyl acetate and filter through a short plug of celite with additional ethyl acetate. Wash the organics with water, dry over magnesium sulfate, filter and evaporate. Purification by flash column chromatography yields 2'-chlorobiphenyl-4-carboxylic acid methyl ester as a yellow solid. Dissolve the purified ester in tetrahydrofuran (0.25M) and add an equal volume of 1M sodium hydroxide. Stir vigorously at room temperature for 15 hours. Upon completion, acidify the reaction with conc. HCl and extract with ethyl acetate. Evaporation of the solvent yields 762 mg (67%) of the title compound. MS (m/e): 231. 1 (M-).
	With sodium carbonate;palladium diacetate; triphenylphosphine; In DMF (N,N-dimethyl-formamide); water; at 80℃; for 1h;	Combine methyl-4-bromobenzoate (1.0 g, 4.65 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (799 mg, 5.1 mmol), Pd (OAC) 2 (51 mg, 0.46 mmol) and sodium carbonate (1.5 g, 13.9 mmol) in DMF (20 mL) and water (2.0 mL) with stirring. Purge the reaction mixture with argon, add triphenylphosphine (61 mg, 0.23 mmol) and purge again with argon. Place the sealed reaction in an oil bath maintained at 80C and allow to stir for 1 hour. Cool the reaction to room temperature, dilute with ethyl acetate and filter through a short plug OF CELITE with additional ethyl acetate. Wash the organics with water, dry over MGS04, filter and evaporate. Purification by flash column chromatography yields 2'- chlorobiphenyl-4-carboxylic acid methyl ester as a yellow solid. Dissolve the purified ester in THF (0.25M) and add an equal volume of 1M NAOH. Stir vigorously at room temperature for 15 hours. Upon completion, acidify the reaction with conc. HCL and extract with ethyl acetate. Evaporation of the solvent yields 762 mg (67%) of the title compound. MS (ES): M/Z 231. 1 (M-1).

Reference： [1]Green Chemistry,2016,vol. 18,p. 967 - 973
[2]RSC Advances,2016,vol. 6,p. 89621 - 89626
[3]Patent: WO2004/94363,2004,A1 .Location in patent: Page 13-14
[4]Patent: WO2005/9941,2005,A1 .Location in patent: Page 13
[5]Patent: WO2004/94382,2004,A1 .Location in patent: Page 13

23
[ 825643-59-2 ]
[ 3900-89-8 ]
[6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-methyl-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium carbonate;palladium diacetate; triphenylphosphine; In 1,2-dimethoxyethane; water; at 80℃; for 1.5h;	A mixture of 6.05 g (19.3 mmol) (6-chloro-4-iodo-pyridin-3-yl)-methyl-amine, 23.6 g (23.6 mmol) <strong>[3900-89-8]2-chlorophenylboronic acid</strong>, 441 mg (1.96 mmol) palladium (II) acetate, 1.03 g (3.93 mmol) triphenylphosphine, 47.1 ml 2 N sodium carbonate solution and 50 ml 1, 2-DIMETHOXYETHANE was heated at 80 °C for 90 min. The reaction mixture was cooled to room temperature and diluted with 100 ml ethyl acetate. The aqueous layer was separated and extracted with 100 ml ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography to give 4.1 g (83percent) of the title compound as a light brown solid. MS mle (percent): 253 (M+H+, 100)
83%	With sodium carbonate; triphenylphosphine;palladium diacetate; In 1,2-dimethoxyethane; water; at 80℃; for 1.5h;	A mixture of 6.05 g (19.3 mmol) (6-chloro-4-iodo-pyridin-3-yl)-methyl-amine, 23.6 g (23.6 mmol) <strong>[3900-89-8]2-chlorophenylboronic acid</strong>, 441 mg (1.96 mmol) palladium(II) acetate, 1.03 g (3.93 mmol) triphenylphosphine, 47.1 ml 2 M sodium carbonate solution and 50 ml 1,2-dimethoxyethane was heated at 80° C. for 90 min. The reaction mixture was cooled to room temperature and diluted with 100 ml ethyl acetate. The aqueous layer was separated and extracted with 100 ml ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography to give 4.1 g (83percent) of the title compound as a light brown solid. MS m/e (percent): 253 (M+H+, 100)

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3405 - 3408
[2]Patent: WO2005/2577,2005,A1 .Location in patent: Page 129-130
[3]Patent: US2006/30600,2006,A1 .Location in patent: Page/Page column 13

24
[ 830346-33-3 ]
[ 3900-89-8 ]
[ 830345-95-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; for 16h;	To compound 5b (10.45 g, 20 mmol) in dioxane/water (180/20 mL) was added <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (6.26 g, 40 mmol) and Na2CO3 (12.72 g, 120 mmol). The mixture was deoxygenated with N2 for 15 minutes, tetrakis (triphenylphosphine) palladium (0) (2.31 g, 2 mmol) was added and the reaction mixture was heated at 90 °C for 16 hours. The reaction was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over NA2S04, concentrated and purified by column chromatography on silica gel with ethyl acetate/hexanes/triethylamine 500/500/6 to 800/200/7 to afford compound 5c (7.26 g, 70 percent) as a white foam. MS (CI) m/z 518. 0, 520.1 (MH+).
70%		To compound lb (10.45 g, 20 mmol) in dioxane/water (180/20 mL) was added <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (6.26 g, 40 mmol) AND NA2CO3 (12.72 g, 120 mmol). The mixture was deoxygenated with N2 for 15 minutes, tetrakis (triphenylphosphine) palladium (0) (2.31 g, 2 mmol) was added and the reaction mixture was heated at 90 oC for 16 hours. The reaction was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over NA2S04, concentrated and purified by column chromatography on silica gel with ethyl ACETATE/HEXANES/TRIETHYLAMINE 500/500/6 to 800/200/7 to afford compound lc (7.26 g, 70 percent) as a white foam. MS (CI) M/Z 518. 0, 520.1 (MH+).

Reference： [1]Patent: WO2005/7165,2005,A1 .Location in patent: Page 40
[2]Patent: WO2005/7633,2005,A1 .Location in patent: Page 29

25
[ 36178-05-9 ]
[ 3900-89-8 ]
[ 847687-41-6 ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium carbonate; In water; acetonitrile; at 60 - 75℃; for 5h;	Example 4: (2S)-2-[[3-(2-chlorophenyl)pyridin-2-yl]thio}(phenyl)methyl]morpholine fumarate /C CI / H SH I/I I/ tPh H S O Ph J H N H Fumarate salt i) To palladium acetate (0.0025 g, 0.0011 mmole) in acetonitrile (3 ml), is added triphenylphosphine (0.0119 g, 0.045 mmole), under nitrogen, at room temperature. The mixture is left to stir for 15 minutes. To this mixture is added water (distilled, 1 ML), 2-chlorophenylboronic acid (0.106 g, 0.68 mmole), 3-BROMO-2-FLUOROPYRIDINE (0.10 g, 0.57 mmole) and potassium carbonate (0.470 g, 3.40 mmole). The reaction mixture is heated to 60°C increasing to 75 °C over 5 hours then allowed to cool to room temperature. To the reaction mixture is added MeOH and this is loaded onto an SC10-2 column (10 g) preconditioned with MeOH. The column is washed with MeOH and the resulting solution concentrated in vacuo to give an orange oil (0.196 g). The oil is purified by automated flash chromatography (ISCO System, a 10 g Redisep SiO2 column, 0-30 percent ethyl acetate in cyclohexane gradient elution over 40 minutes). This gave 2-fluoro-3- (2-chlorophenyl) pyridine as a colourless oil (0.050 g, 42 percent). LCMS 6 min gradient method, Rt = 3.3 min, (M+H+) = 208
42%	With potassium carbonate; triphenylphosphine;palladium diacetate; In water; acetonitrile; at 20 - 75℃; for 5.25h;	To palladium acetate (0.0025 g, 0.0011 mmole) in acetonitrile (3 ml), is added triphenylphosphine (0.0119 g, 0.045 mmole), under nitrogen, at room temperature. The mixture is left to stir for 15 minutes. To this mixture is added water (distilled, 1 ml), 2- chlorophenylboronic acid (0.106 g, 0.68 mmole), 3-BROMO-2-FLUOROPYRIDINE (0.10 g, 0.57 mmole) and potassium carbonate (0.470 g, 3.40 mmole). The reaction mixture is heated to 60°C increasing to 75 °C over 5 hours then allowed to cool to room temperature. To the reaction mixture is added MeOH and this is loaded onto an SC10-2 column (10 g) preconditioned with MeOH. The column is washed with MeOH and the resulting solution concentrated IN VACUO to give an orange oil (0.196 g). The oil is purified by automated flash chromatography (ISCO System, a 10 g Redisep SI02 column, 0-30 percent ethyl acetate in cyclohexane gradient elution over 40 minutes). This gave 2-fluoro-3- (2- chlorophenyl) pyridine as a colourless oil (0.050 g, 42 percent). LCMS 6 min gradient method, RT = 3.3 min, (M+H+) = 208
42%	With potassium carbonate; triphenylphosphine;palladium diacetate; In water; acetonitrile; at 20 - 75℃; for 5.25h;Heating / reflux;	To palladium acetate (0.0025 g, 0.0011 mmole) in acetonitrile (3 ml), is added triphenylphosphine (0. 0119 g, 0.045 mmole), under nitrogen, at room temperature. The mixture is left to stir for 15 minutes. To this mixture is added water (distilled, 1 ml), 2- chlorophenylboronic acid (0.106 g, 0.68 mmole), <strong>[36178-05-9]3-bromo-2-fluoropyridine</strong> (0.10 g, 0.57 mmole) and potassium carbonate (0.470 g, 3.40 mmole). The reaction mixture is heated to 60°C increasing to 75 °C over 5 hours then allowed to cool to room temperature. To the reaction mixture is added MeOH and this is loaded onto an SC10-2 column (10 g) preconditioned with MeOH. The column is washed with MeOH and the resulting solution concentrated in vacuo to give an orange oil (0.196 g). The oil is purified by automated flash chromatography (ISCO System, a 10 g Redisep SiO2 column, 0-30 percent ethyl acetate in cyclohexane gradient elution over 40 minutes). This gave 2-fluoro-3- (2- chlorophenyl) pyridine as a colourless oil (0.050 g, 42 percent). LCMS 6 min gradient method, Rt = 3.3 min, (M+H+) = 208

Reference： [1]Patent: WO2005/23802,2005,A1 .Location in patent: Page/Page column 40-41
[2]Patent: WO2005/20976,2005,A2 .Location in patent: Page/Page column 257-258
[3]Patent: WO2005/60949,2005,A2 .Location in patent: Page/Page column 256

26
[ 666730-32-1 ]
[ 3900-89-8 ]
4-[2-(2-Chloro-phenyl)-6-methyl-pyridin-3-yloxy]-6,7-dimethoxy-quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 80℃; for 3h;	Compound 228: 4-[2-(2-Chloro-phenyl)-6-methyl-pyridin-3-yloxy]-6,7-dimethoxy-quinoline; Toluene (0.7 ml) and a saturated aqueous sodium hydrogencarbonate solution (0.35 ml) were added to 4-(2-iodo-6-methyl-pyridin-3-yloxy)-6,7-dimethoxy-quinoline (compound 116) (50 mg), tetrakistriphenylphosphine palladium (14 mg), and 2-chlorophenyl boronic acid (81 mg) under an argon atmosphere, and the mixture was stirred at 80°C for 3 days. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-acetone to give the title compound (43 mg, yield 90percent). 1H-NMR (CDCl3, 400 MHz): delta 2.68 (s, 3H), 4.00 (s, 3H), 4.00 (s, 3H), 6.41 (d, J = 5.4 Hz, 1H), 7.10 - 7.17 (m, 2H), 7.17 - 7.29 (m, 4H), 7.44 (s, 1H), 7.52 (d, J = 5.6 Hz, 1H), 8.42 (d, J = 5.1 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 407 (M+1)+

Reference： [1]Patent: EP1548008,2005,A1 .Location in patent: Page/Page column 122-123

27
[ 864543-70-4 ]
[ 3900-89-8 ]
[ 864543-71-5 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; water; benzene; for 5h;Heating / reflux;	Step 11. Preparation of3-(2-chlorophenyl)-6-(2,4-difluorophenoxy)-pyrazolo[4, 3-c]pyridine- 1-carboxylicad, tert-butyl ester.; A solution of l-BOC-6-(2,4-difluorophenoxy)-3-iodo-lH-pyrazolo[4,3-c]pyridine (0.071 g) and <strong>[3900-89-8]2-chlorophenylboronic acid</strong> in 5 mL of benzene and 1 mL of methanol was stirred at RT for 15 min. To this solution was added tetrakis(triphenylphosphine)palladium catalyst (52 mg) and 0.3 mL of 1 M sodium carbonate. The resulting mixture was heated to reflux for five hours, cooled, filtered and the organic layer was separated. The organic layer was washed, dried and concentrated. The residue was purified via chromatography EPO <DP n="47"/>using 5percent ethyl acetate in hexane as the eluent to afford 45 mg of 3-(2-chlorophenyl)-6- (2,4-difluorophenoxy)-pyrazolo[4, 3-c] pyridine- 1-carboxylic acid, tert-butyl ester (66percent yield). Mass. Spec. M+H = 458.
66%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In methanol; benzene; at 20℃; for 5.25h;Heating / reflux;	A solution of 1-BOC-6-(2,4-difluorophenoxy)-3-iodo-1H-pyrazolo[4,3-c]pyridine (0.071 g) and <strong>[3900-89-8]2-chlorophenylboronic acid</strong> in 5 mL of benzene and 1 mL of methanol was stirred at room temperature for 15 minutes. To this solution was added tetrakis(triphenylphosphine)palladium catalyst (52 mg) and 0.3 mL of 1 M sodium carbonate. The resulting mixture was heated to reflux for five hours, cooled, filtered and the organic layer was separated. The organic layer was washed, dried and concentrated. The residue was purified via chromatography using 5percent ethyl acetate in hexane as the eluent to afford 45 mg of 3-(2-chlorophenyl)-6-(2,4-difluorophenoxy)-pyrazolo[4,3-c]pyridine-1-carboxylic acid, tert-butyl ester (66percent yield). Mass. Spec. M+H=458.

Reference： [1]Patent: WO2007/23105,2007,A1 .Location in patent: Page/Page column 45-46
[2]Patent: US2005/203091,2005,A1 .Location in patent: Page/Page column 47
[3]Heterocycles,2009,vol. 78,p. 2811 - 2826

28
[ 1072-97-5 ]
[ 3900-89-8 ]
5-(2-chloro-phenyl)-pyridin-2-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; benzene; at 20℃; for 24h;Heating / reflux;	A suspension of 70 mg (0.06 mmol) of tetrakis(triphenylphosphine) palladium(0) in benzene (4 ml) was treated at RT under an argon atmosphere successively with 0.35 g (2 mmol) of 2-amino-5-bromo-pyridine, 2.2 ml (4.4 mmol) of 2 M aqueous Na2CO3 solution, 0.34 g (2.2 mmol) of <strong>[3900-89-8]2-chlorophenylboronic acid</strong> in ethanol (1 ml) and heated to reflux for 24 h. The reaction mixture was cooled and partitioned between EtOAc and water. The layers were separated, the organic layer dried over sodium sulphate and concentrated in vacuo. The residue was applied to a silica gel column with EtOAc as eluent. Combination of the purified fractions and concentration in vacuo gave 0.4 g (98percent) of the desired 5-(2-chloro-phenyl)-pyridin-2-ylamine as white crystalline solid. ISP mass spectrum, m/e: 205.1 (M+1 calculated for C11H9ClN2: 205).

Reference： [1]Patent: US2006/25455,2006,A1 .Location in patent: Page/Page column 12

29
[ 904297-87-6 ]
[ 3900-89-8 ]
benzoic acid N'-[2-(2'-chloro-5-fluoro-biphenyl-2-yloxy)-acetyl]-N'-isopropyl-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃; for 12h;	A solution of benzoic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide (60 mg, 0.147 mmol) in DME (3 ml)/2M Na2CO3 (256 uL, 0.513 mmol) was treated with 3-chlorophenylboronic acid (34 mg, 0.219 mmol) and Pd[PPh3]4 (34 mg, 0.029 mmol) for 12 hours at 90° C. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 30-50percent ethyl acetate/hexanes gradient to afford the product as a white crystalline solid (52 mg, 80percent). LC-MS m/e 441.24 (M+H+)

Reference： [1]Patent: US2006/178532,2006,A1 .Location in patent: Page/Page column 18

30
[ 913628-28-1 ]
[ 3900-89-8 ]
[ 913628-36-1 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃;	General procedure to generate biaryl derivatives from toluene-4-sulfonic acid 8-trifluoromethanesulfonyloxy-2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl ester: To a solution of toluene-4-sulfonic acid 8-trifluoromethanesulfonyloxy-2,3-dihydrobenzo[1,4]dioxin-2-ylmethyl ester (1.0 eq) and substituted benzene boronic acid (2 eq) in DME-water (4/1) was added tetrakis(triphenylphospine)palladium (0) (0.03 eq) and sodium carbonate (2.5 eq). The reaction mixture was heated at 80° C. until starting material was gone. The mixture was filtered through the pad of celite and concentrated under vacuum. Chromatography with 10percent ethyl acetate in hexanes afforded product as an oil. Using the general procedures outlined above, Intermediates 8-41 can be prepared. Intermediate 8 Toluene-4-sulfonic acid 8-(2-chlorophenyl)-2,3-dihydro-benzo[1,4]dioxin-2-yl-methyl ester: Starting from toluene-4-sulfonic acid 8-trifluoromethanesulfonyloxy-2,3-dihydrobenzo-[1,4]dioxin-2-ylmethyl ester (0.235 g, 0.5 mmol) and 2-chlorobenzene boronic acid, 142 mg (66percent) of the title compound was obtained as a colorless oil.

Reference： [1]Patent: US2006/241172,2006,A1 .Location in patent: Page/Page column 51

31
[ 913629-97-7 ]
[ 3900-89-8 ]
[ 913630-09-8 ]

Yield	Reaction Conditions	Operation in experiment
81%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 80℃;	General procedure to generate biaryl derivatives from toluene-4-sulfonic acid 4-bromo-6-chloro-benzo[1,3]dioxol-2-yl-methyl ester To a solution of toluene-4-sulfonic acid 4-bromo-6-chloro-benzo[1,3]dioxol-2-yl-methyl ester (1.0 eq) and substituted benzene boronic acid (3 eq) in DME-water (4/1) was added tetrakis(triphenylphospine)palladium (0) (0.1 eq) and sodium carbonate (3 eq). The reaction mixture was heated at 80° C. until starting material was gone. The mixture was filtered through the pad of celite and concentrated under vacuum. Chromatography with 10percent ethyl acetate in hexanes afforded the title compounds. Using the general procedure outlined above, INTERMEDIATES 186-197 can be prepared. Intermediate 186 Toluene-4-sulfonic acid 4-(2-chloro-phenyl)-6-chloro-benzo[1,3]dioxol-2-yl-methyl ester: Starting from toluene-4-sulfonic acid 4-bromo-6-chloro-benzo[1,3]dioxol-2-yl-methyl ester (0.30 g, 0.71 mmol) and 2-chlorobenzene boronic acid (0.33 g, 2.1 mmol), the general procedure described above gave the title compound (0.28 g, 81percent) as a colorless oil.

Reference： [1]Patent: US2006/241172,2006,A1 .Location in patent: Page/Page column 66

32
[ 913824-85-8 ]
[ 3900-89-8 ]
[ 913824-86-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 1.33333h;	A mixture of (8-[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2H~chromen-2- yl)methyl 4-methylbenzenesulfonate (0.49 g, 1.05 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (0.33 g, 2.1 mmol), potassium carbonate (0.44 g, 3.2 mmol) and lithium chloride (0.13 g, 3.1 mmol) in dioxane (3.75 ml) and water (1.25 mL) was purged with nitrogen for 20 minutes. Tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.052 mmol) was added and the reaction mixture heated at 100 °C for 1 hour. The cooled reaction mixture was then partitioned between ethyl acetate (50 mL) and 1 M aqueous sodium hydroxide (50 mL). The organic layer was separated, washed with water (50 mL) dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford an orange oil. Purification by flash chromatography using a solvent gradient of 5 to 10percent ethyl acetate in hexane gave 400 mg(89percent) of r8-r2-chlorophenylV3,4-dihvdro-2H-chromen-2-yllmethyl 4= methylbenzenesulfonate as a white solid. HRMS : calcd for C23H21ClO4S + NH4+, 446.11873; found (ESI, [M+NH4]+), 446.1179.

Reference： [1]Patent: WO2006/116165,2006,A1 .Location in patent: Page/Page column 70

33
[ 913824-89-2 ]
[ 3900-89-8 ]
[(2R)-8-(2-chlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate; lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 4.5h;	A mixture of ((2i?)-8-[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2H"-chromen-2- yl)methyl 4-methylbenzenesulfonate, prepared in Example 3, step 1 (0.50 g, 1.1 mmol), 2- chlorophenylboronic acid (0.34 g, 2.2 mmol), potassium carbonate (0.46 g, 3.3 mmol) and lithium chloride (0.14 g, 3.3 mmol) in dioxane (3.75 mL) and water (1.25 mL) was purged with nitrogen for 30 minutes. Tetrakis(triphenylphosphine)palladium (0) (60 mg, 0.052 mmol) was added and the reaction mixture heated to 100 °C for 4 hours. The cooled reaction mixture was then partitioned between ethyl acetate (15 mL) and 1 M aqueous sodium hydroxide (15 mL). The organic layer was separated, washed with saturated brine (15 mL) dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford an orange oil. Purification by flash chromatography using a solvent gradient of 5 to 20percent ethyl acetate in hexane gave 0.38 g (81percent) of r(2i?V8-(2-chlorophenylV3,4-dihydro-2H-chromen-2- yllmethyl 4-methylbenzene sulfonate as a white solid. HRMS: calcd for C23H21ClO4S + H+, 429.09218; found (ESI, [MH-H]+), 429.0924.

Reference： [1]Patent: WO2006/116165,2006,A1 .Location in patent: Page/Page column 74

34
[ 915034-55-8 ]
[ 3900-89-8 ]
benzoic acid N'-[3-(2'-chloro-biphenyl-2-yl)-propionyl]-N'-isopropyl-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; at 90℃; for 18h;	A solution of benzoic acid N'-[3-(2-bromo-phenyl)-propionyl]-N'-isopropyl-hydrazide (45 mg, 0.12 mmol) in DME (4 ml)/2M Na2CO3 (225 muL, 0.45 mmol) was treated with 2-chloro-phenylboronic acid (27 mg, 0.17 mmol) and Pd[PPh3]4 (13 mg, 0.012 mmol) for 18 hours at 90° C. The reaction mixture was partitioned between water and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 30-50percent ethyl acetate/hexanes gradient to afford the product as a solid (46 mg, 94percent). LC-MS m/e 421.27 (M+H+)

Reference： [1]Patent: US2006/258740,2006,A1 .Location in patent: Page/Page column 18

35
[ 4521-30-6 ]
3-(2-chlorophenyl)-5-methoxycarbonyl-1-phenyl-1,2-dihydropyridin-2-one [ No CAS ]
[ 79-37-8 ]
[ 381248-00-6 ]
[ 3900-89-8 ]
3-(2-Chlorophenyl)-5-(2-benzothiazolyl)-1-phenyl-1,2-dihydropyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; PPA; sodium bicarbonate;N-methyl-acetamide; In dichloromethane;	Example 183. 3-(2-Chlorophenyl)-5-(2-benzothiazolyl)-1-phenyl-1,2-dihydropyridin-2-one 19mg of carboxylate obtained by hydrolyzing the ester group of 3-(2-chlorophenyl)-5-(methoxycarbonyl)-1-phenyl-1,2-dihydropyridin-2-one (synthesised from 3-bromo-5-(methoxycarbonyl)-1-phenyl-1,2-dihydropyridin-2-one and 2-chlorophenylboronic acid in accordance with the method for Referential Example 3) was dissolved in 20ml of dichloromethane. Under ice-cooling, a solution of 11mg of oxalyl chloride in dichloromethane was added dropwise thereinto and a catalytic amount of dimethylformamide was added thereto, followed by stirring at room temperature in nitrogen atmosphere for 1 hour. The reaction solution was evaporated, and the residue was dissolved in dichloromethane. The solution was added dropwise into a solution of 22mg of <strong>[4521-30-6]2-aminobenzothiol</strong> in dichloromethane under ice-cooling. After heating to room temperature, dichlotomethane was evaporated. To the residue was added 1ml of polyphosphoric acid, followed by stirring at 180C overnight. After cooling to room temperature, the reaction mixture wasneutralized with 1N aqueous solution of sodium hydroxide and saturated aqueous solution of sodium hydrogen carbonate under ice-cooling and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 4mg of the title compound as white crystals.1H-NMR (400MHz, CDCl3); delta(ppm) 7.32-7.35(m,2H), 7.37-7.41(m,1H), 7.46-7.51(m,4H), 7.51-7.55(m,4H), 7.87-7.89(m,1H), 8.00(d,1H), 8.14(d,1H), 8.42(d,1H). ESI-Mass; 415 [M++H]

Reference： [1]Patent: EP1300396,2003,A1

36
[ 917486-05-6 ]
[ 3900-89-8 ]
[ 917486-06-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium phosphate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In tetrahydrofuran; at 70℃; for 16.25h;	1C. Preparation of 2-benzyl-6-(2-chlorophenyl)-5-(4-chlorophenyl)pyridazin-3(2H)-one; To a flame-dried round bottom flask was placed 2-benzyl-6-chloro-5-(4-chlorophenyl)pyridazin-3(2H)-one (6.0 g, 18.1 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (5.7 g, 36.2 mmol), K3PO4 (7.7 g, 36.2 mmol), and [1,1'bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with CH2Cl2 (1:1) (2.96 g, 3.6 mmol). The flask was purged with argon for 15 min before degassed THF (120 mL) was added. The reaction mixture was stirred in a 70° C. oil bath under argon for 16 h. After cooling to room temperature, the reaction mixture was diluted with EtOAc (200 mL), washed with 1N aqueous NaOH (50 mL), H2O, saturated aqueous NaCl, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified using a silica gel cartridge (330 g) eluting with a gradient of EtOAc (0-40percent) in hexanes to afford 6.5 g (88percent) of the title compound as a white solid. HPLC/MS (method A): retention time=3.97 min, (M+H)+=407.0. 1H NMR (CDCl3, 400 MHz): delta7.51 (d, 2H, J=8.0 Hz), 7.24-7.40 (m, 9H), 6.95-7.03 (m, 3H), 5.33 (s, 2H).
88%	With potassium phosphate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In tetrahydrofuran; at 70℃; for 16h;	1C. Preparation of 2-benzyl-6-(2-chlorophenyl)-5-(4-chlorophenyl)pyridazin-3(2H)-one To a flame-dried round bottom flask was placed 2-benzyl-6-chloro-5-(4-chlorophenyl)pyridazin-3(2H)-one (6.0 g, 18.1 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (5.7 g, 36.2 mmol), K3PO4 (7.7 g, 36.2 mmol), and [1,1'-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex with CH2Cl2 (1:1) (2.96 g, 3.6 mmol). The flask was purged with argon for 15 min before degassed THF (120 mL) was added. The reaction mixture was stirred in a 70° C. oil bath under argon for 16 h. After cooling to room temperature, the reaction mixture was diluted with EtOAc (200 mL), washed with 1N aqueous NaOH (50 mL), H2O, saturated aqueous NaCl, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified using a silica gel cartridge (330 g) eluding with a gradient of EtOAc (0-40percent) in hexanes to afford 6.5 g (88percent) of the title compound as a white solid. LC/MS (method A): retention time=3.97 min, (M+H)+=407. 1H NMR (CDCl3, 400 MHz): delta 7.51 (d, 2H, J=8.0 Hz), 7.24-7.40 (m, 9H), 6.95-7.03 (m, 3H), 5.33 (s, 2H).

Reference： [1]Patent: US2006/287324,2006,A1 .Location in patent: Page/Page column 11
[2]Patent: US2006/287322,2006,A1 .Location in patent: Page/Page column 10

37
4-bromo-3-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1-methyl-1H-pyrazole [ No CAS ]
[ 3900-89-8 ]
4-(2-chlorophenyl)-3-[5-(3-methanesulfonyl-phenyl)-thiophen-2-yl]-1-methyl-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 80℃; for 4h;	Example 3e; Preparation of 4-(2-c}?lpsifOphepsil)-3-[5-(3-methamsulfopsilpsihepsil)-thiophen-2-ylJ-l-me pyrazoleA mixture of 4-bromo-3-[5-(3-me1hanesuIfonyl-phenyl)-thiophen-2-yl]-l-methyl-1H-pyrazole (88 mg, 0.22 mmol), 2-cbJorophenylboronic acid (41 mg, 0.26 mmol), K2CO3 (91 mg, 0.66 mmol), Cl2Pd(drhopf)-DCM (18 mg, 10 molpercent) and H2O (0.25 mL) in dioxane (2.5 mL) was sparged with Argon EPO <DP n="133"/>for 5 min and then heated at 80°C as a sealed flask. After 4 h the reaction mixture was allowed to cool to ambient temperature, filtered (Celite.(TM).) and the filter agent rinsed with EtOAc. The combined filtrates were concentrated under reduced pressure and purified by chromatography (silica, EtOAc/Hex, 30:70 to 40:60) to give the title compound (64 mg, 67percent). R/0.14 (40percent EtOAc/Hex); 1H-NMR (CD2Cl2): delta 8.09 (IH, m), 7.85-7.76 (2H, m), 7.60-7.49 (2H, m), 7.45 (IH, s), 7.41-7.30 (3H, m), 7.21 (IH, d), 6.70 (IH, d), 3.97 (3H, s), 3.05 (3H, s); MS (ES): 429 [M+Hf

Reference： [1]Patent: WO2007/2559,2007,A1 .Location in patent: Page/Page column 131-132

38
4-(4-bromo-benzyl)-2-pyridin-3-yl-morpholine [ No CAS ]
[ 3900-89-8 ]
2-pyridin-3-yl-4-(2'-chloro-biphenyl-4-ylmethyl)-morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 120℃;	2-Pyridin-3-yl-4-(2'-chloro-biphenyl-4-ylmethyl)-morpholine ; <n="41"/>105mg of 4-(4-Bromo-ben2yl)-2-pyridin-3-yl-morpholine was combined with 74mg of 2- Chlorophenyl boronic acid, 36mg of tetrakis(triphenylphosphine)palladium(0), 1.055mL of 2M sodium, carbonate solution, 2.8mL toluene and 1.4mL ethanol. The reaction mixture was heated in a sealed tube at 120°C overnight in an oil bath. The reaction mixture was filtered through Celite and concentrated in vacuo. The residue was purified by reverse phase HPLC. ES MS (+) m/z 365, 97percent yield.

Reference： [1]Patent: WO2007/70760,2007,A2 .Location in patent: Page/Page column 39-40

39
[ 942123-11-7 ]
[ 3900-89-8 ]
[ 942122-34-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 85℃;	Example 107:(S) 3-Benzyl-l-(2'-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine; Ig of 3-(S)-benzyl-l-(4-bromo-benzyl)-piperazine were combined with 1.5 equiv. of 2- chlorophenyl boronic acid, 0.05 equiv. of tetrakis(triphenylphosphine)palladium(0), 6 equiv. of 2M aqueous sodium carbonate solution, toluene and ethanol. The reaction mixture was heated at 850C under nitrogen overnight. The reaction mixture was concentrated in vacuo. The residue was diluted with water and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography to afford 0.98g of the title compound. Yield 91percentES MS (+) m/z 377.

Reference： [1]Patent: WO2007/70760,2007,A2 .Location in patent: Page/Page column 77

40
3-(R)-benzyl-1-(4-bromo-benzyl)-piperazine [ No CAS ]
[ 3900-89-8 ]
(R)-3-benzyl-1-(2'-chloro-biphenyl-4-ylmethyl)-piperazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 85℃;	Example 108:(R) 3-Benzyl-l-(2'-trifluoromethyl-biphenyl-4-ylmethyl)-piperazine; 0.28g of 3-(S)-ben2yl-l-(4-bromo-benzyl)-piperazine were combined with 1.5 equiv. of 2- chlorophenyl boronic acid, 0.05 equiv. of tetrakis(triphenylphosphine)palladium(0), 6 equiv. of 2M aqueous sodium carbonate solution, toluene and ethanol. The reaction mixture was heated at 85°C under nitrogen overnight. The reaction mixture was concentrated in vacuo. The <n="79"/>residue was diluted with water and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography to afford 0.26g of the title compound. Yield 84percentES MS (+) m/z 377.

Reference： [1]Patent: WO2007/70760,2007,A2 .Location in patent: Page/Page column 77-78

41
[ 1065482-54-3 ]
[ 3900-89-8 ]
[ 1065482-55-4 ]

Yield	Reaction Conditions	Operation in experiment
97.24%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; acetonitrile; at 100℃; for 4h;	3-(2-Chlorophenyl)-2-methyl-5-(trifluoromethyl)quinoxaline; A mixture of 3-chloro-2-methyl-5-(trifluoromethyl)quinoxaline (0.7939 g, 3.219 mmol), [Reactants], tetrakis(triphenylphosphine)palladium (0.1860 g, 0.1610 mmol), and sodium carbonate anhydrous (1.706 g, 16.10 mmol) in CH3CN-H2O (3 : 1 ) (32.00 mL) was stirred at 1000C. After 4 h, the mixture was cooled to room temperature and partitioned between EtOAc (100 mL) and water (100 mL). The organic layer was washed with brine (50 mL x 2), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography on a 80 g of Redi-Sep.(TM). column using 0 to 50percent gradient of EtOAc in hexane over 15 min and then 50percent isocratic of EtOAc for 4 min as eluent to give 3-(2-chlorophenyl)-2-methyl-5-(trifluoromethyl)quinoxaline as an <n="214"/>orange syrup: 1H NMR (400 MHz, DMSO-d6) delta ppm 8.36 - 8.41 (1 H, m), 8.25 (1 H, d, J=7.4 Hz)5 8.01 (1 H, t, J=7.8 Hz), 7.66 - 7.71 (1 H, m), 7.54 - 7.65 (3 H, m), 2.54 (3 H, s); LC-MS (ESI) m/z 323.0 [M+H]+.

Reference： [1]Patent: WO2008/118468,2008,A1 .Location in patent: Page/Page column 212-213

42
[ 1021860-17-2 ]
[ 3900-89-8 ]
[ 1021860-18-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium carbonate;dichlorobis(tri-O-tolylphosphine)palladium; In 1,4-dioxane; water; at 90℃; for 0.5h;	To a solution of tert-butyl 8-bromo-2-(hydroxymethyl)-2H- benzo[delta][l,4]oxazine-4(3H)carboxylate (0.49 g, 0.98 mmol) and 2-chlorobenzene boronic acid (0.64 g, 3.9 mmol) in dioxane-water (4/1, 10 mL) was added dichlorobis(tri-o- tolyphosphine)-palladium (II) (0.04 g) and potassium carbonate (0.34 g, 2.5 mmol). The reaction mixture was heated at 9O0C for 0.5 h. The mixture was filtered through a pad of celite and concentrated under vacuum. ISCO CombiFlash.(R). chromatography with 10-30 percent EPO <DP n="90"/>ethyl acetate in hexanes afforded the title product 0.4 g (77percent) as a colorless oil. MS (ES) m/z 547.2 [M + NH4J+.

Reference： [1]Patent: WO2008/52075,2008,A2 .Location in patent: Page/Page column 88-89

43
[ 3900-89-8 ]
[ 81565-18-6 ]
[ 1057722-61-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With barium dihydroxide;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 110℃; for 1h;	Example 1 : <n="48"/>Step (i) :2- (2-chlorophenyl) -4- (trifluoromethyl) pyridine [00140] A mixture of 2-chloro-4- (trifluoromethyl) pyridine (4 g, 22.0 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (5.04 g, 24.2 mmol), Ba(OH)2 (12.5 g, 66.1 mmol) and Pd(PPh3)2Cl2 (464 mg, 0.66 mmol) in DME (140 mL) /water (35 mL) was heated at 110 0C for 1 h. The solids were filtered off and the mother liquor were concentrated to around 80 mL and extracted with EtOAc. The organic layer was washed with brine, then water, dried (MgSO4) , filtered and concentrated. Purification by column chromatography (1/1 Petroleum ether/EtOAc) gave the Suzuki adduct (5.05 g, 89percent) as a colourless oil. 1H NMR (400 MHz, CDCl3): 7.41-7.44 (2H, m) , 7.51-7.56 (2H, m) , 7.63-7.65 (IH, m) , 7.94 (IH, s), 8.94 (IH, d) .
	With barium dihydroxide;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 110℃;	Reagents and conditions: (i) mCPBA, EtOAc; (ii) POCl3; (iii) PdPPh3) 2C12, Ba(OH)2, DME-H2O, 110 0C; (iv) 5-fluoro-lH- pyrazolo [3, 4-b] pyridin-3-amine, Pd(OAc)2, Xantphos, K2CO3, dioxane, 120 0C.[0054] Scheme III above shows a general synthetic route that is used for preparing the compounds III-5. Compounds of formula III-5 can be prepared from intermediate III-l. The formation of chloropyridine derivative III-2 is achieved by treating the corresponding pyridine III-l with m-CPBA in EtOAc followed by conversion of the corresponding N-oxide to the chloropyridine by treating it with POCl3. Intermediate III-2 is then reacted with the corresponding boronic acid derivative to yield compound III- 3 using Suzuki coupling conditions well known for those skilled in the art. This reaction is amenable to a variety of boronic acid derivatives. The pyridine III-3 is then converted in a chloropyridine derivative III-4 using the same two step procedures as used in step 1, m-CPBA oxidation followed by POCl3 treatment. Intermediate III-4 is then treated with 5-fluoro-lH- <n="25"/>pyrazolo [3, 4-b] pyridin-3-amine in the presence of Pd as a catalyst to yield the final compound III-5.
	With barium(II) hydroxide;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 110℃; for 1h;	EXAMPLE 5: COMPOUND 1-32; Step (i): 2-(2-chlorophenyI)-4-(trifluoromethyl)pyridine; [00204] A mixture of 2-chloro-4-(trifluoromethyl)pyridine (4 g, 22.0 mmol), 2- chlorophenylboronic acid (5.04 g, 24.2 mmol), Ba(OH)2 (12.5 g, 66.1 mmol) and Pd(PPh3)2Cl2 (464 mg, 0.66 mmol) in DME (140 mL)/water (35 mL) was heated at 110 0C for 1 hour. The solids were filtered off and the mother liquors were concentrated to around 80 mL and extracted with EtOAc. The organic layer was washed with brine then water, dried (MgSO4), filtered and concentrated. Purification by column chromatography (1/1 Petroleum ether/EtOAc) gave the Suzuki adduct (5.05 g, 89percent) as a colourless oil. <n="57"/>1H NMR (400 MHz, CDCl3): 7.41-7.44 (2H, m), 7.51-7.56 (2H, m), 7.63-7.65 (IH, m), 7.94 (IH, s), 8.94 (IH, d).

Reference： [1]Patent: WO2008/112646,2008,A1 .Location in patent: Page/Page column 46-47
[2]Patent: WO2009/18415,2009,A1 .Location in patent: Page/Page column 23-24; 43
[3]Patent: WO2009/145814,2009,A2 .Location in patent: Page/Page column 55-56

44
[ 1078166-46-7 ]
[ 3900-89-8 ]
[ 1078167-08-4 ]

Yield	Reaction Conditions	Operation in experiment
71%	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 100℃; for 0.5h;	EXAMPLE 39 3-[(2'-Chlorobiphenyl-4-yl)oxy]methyl}-1-(4-fluorobenzoyl)azetidine-3-carboxylic acid 2-Chlorophenylboronic acid (23 mg, 0.147 mmol), cesium carbonate (50 mg, 0.147 mmol) and then tetrakis(triphenylphosphine)palladium(0) (8.5 mg, 0.007 mmol) were added to a stirred solution of 3-[(4-bromophenoxy)methyl]-1-(4-fluorobenzoyl)azetidine-3-carboxylic acid (30 mg, 0.07 mmol) (Preparation 9) in 1,4-dioxane and water (1:1, 3 mL). The mixture was heated to 100° C. for 0.5 hours. The reaction mixture was then allowed to cool before being partitioned between diethyl ether (15 mL) and 2M sodium hydroxide (10 mL). The aqueous layer was made acidic with aqueous hydrochloric acid (2N, 15 mL) and extracted with diethyl ether (15 mL). The diethyl ether layer was dried over sodium sulphate and concentrated under reduced pressure. The resulting residue was triturated with diethyl ether/pentane (1:1) to afford the title compound as an off-white solid in 71percent yield (22 mg). 1H NMR (400 MHz, DMSO-d6) delta: 4.12 (d, 1H), 4.28 (d, 1H), 4.37 (d, 1H), 4.43 (s, 2H), 4.60 (d, 1H), (d, 1H), 7.03 (d, 2H), 7.25-7.41 (m, 7H), 7.54 (d, 1H), 7.76 (m, 2H); LRMS APCI m/z 440 [MH]+

Reference： [1]Patent: US2008/280877,2008,A1 .Location in patent: Page/Page column 25

45
[ 1021305-22-5 ]
[ 3900-89-8 ]
[ 1021303-31-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium phosphate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; N,N-dimethyl-formamide; at 90℃;	Bromide 6 (1.29 g, 3.31 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (570 mg, 3.65 mmol), K3PO4 (1.55 g, 7.28 mmol) and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (270 mg, 0.33 mmole) were mixed as solids and placed under argon. Argon was then bubbled through a 1:1 mixture of anhydrous DMF (25 mL) and DME (25 mL) for 15 minutes. The solvent was then added to the solid mix and the solution was heated to 90 °C overnight. The solution was cooled, diluted with 250 mL of ethyl acetate and washed with 250 mL of saturated aqueous NaHCO3 and 250 mL of brine. The organic layer was separated, dried with anhydrous sodium sulfate, filtered and concentrated under vacuum to give 2.08 g of crude product. The material was purified via silica gel column chromatography eluting with 5percent methanol/methylene chloride to give 1.54 g (100percent) of product.
100%	With potassium phosphate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; N,N-dimethyl-formamide; at 90℃;	Example 5Bromide 6 (1.29 g, 3.31 mmol), <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (570 mg, 3.65 mmol), K3PO4 (1.55 g, 7.28 mmol) and [1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladiurn(II) complex with dichloromethane (270 mg, 0.33 mmole) were mixed as solids and placed under argon. Argon was then bubbled through a 1 : 1 mixture of anhydrous DMF (25 mL) and DME (25 mL) for 15 minutes. The solvent was then added to the solid mix and the solution was heated to 90 0C overnight. The solution was cooled, diluted with 250 mL of ethyl acetate and washed with 250 mL of saturated aqueous "NaHCO3 and 250 mL of brine. The organic layer was separated, dried with anhydrous sodium sulfate, filtered and concentrated under vacuum to give 2.08 g of crude product. The material was purified via silica gel column chromatography eluting with 5percent methanol/methylene chloride to give 1.54 g (100percent) of product.

Reference： [1]Patent: EP1914234,2008,A1 .Location in patent: Page/Page column 25; 27
[2]Patent: WO2008/150260,2008,A1 .Location in patent: Page/Page column 78; 81

46
[ 3764-01-0 ]
[ 3900-89-8 ]
[ 685866-93-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium carbonate;palladium diacetate; triphenylphosphine; In tetrahydrofuran; water; at 60℃; for 3h;	[00273] To a solution of commercially available 2,4,6-trichloropyridine (5.16g, 28.2 mmol) in THF (40 mL) was added commercially available <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (2.20 g, 14.1 mmol), Pd(OAc)2 (282 mg), PPh3 (660 mg), followed by Na2CO3 (28.2 mL, I M). The reaction was heated to 60 °C for 3 hours and completed. The mixture was partitioned between EtOAc and water. The organic layer was washed with saturated brine, dried and concentrated. The residue was purified by chromatography to 2,4-dichloro-6-(2- chlorophenyl)pyrimidine (2.72 g, 75percent) as a white solid.

Reference： [1]Patent: WO2008/133955,2008,A1 .Location in patent: Page/Page column 117; 118

47
[ 17100-58-2 ]
[ 3900-89-8 ]
[ 1122567-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;palladium diacetate; triphenylphosphine; In propan-1-ol; water; at 80℃; for 2h;	EXAMPLE 1; 2-(2'-Chloro-3-methyl-biphenyl-4-yl)-3 - { 4-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy] -phenyl } - propylamine; Step 1 : (2'-chloro-3-methylbiphenyl-4-yl)methanol; To a solution (4-bromo-2-methylphenyl) methanol (1 eq.) from Benzyl nitrile HLl (Step 1) and 2-chlorophenylboronic acid (1.2 eq.) in fl-propanol (O. IM) was added palladium acetate/triphenyl phosphine (1:3; 0.05 eq.) and aqueous Na2CO3 (2M; 3 eq.). The mixture was stirred at 8O0C for 2h, cooled to room temperature, poored in water and extracted with EtOAc. The organic extract was washed with, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (0 to 75% in 30min) to afforded the desired compound.

Reference： [1]Patent: WO2009/23964,2009,A1 .Location in patent: Page/Page column 32

48
[ 106-38-7 ]
[ 3900-89-8 ]
[ 19493-33-5 ]

Yield	Reaction Conditions	Operation in experiment
71.7%	With C14H8F6O4; nickel trifluoroacetate; potassium carbonate; triphenylphosphine; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide; In water; at 80℃; for 18h;Green chemistry;	General procedure: A 50mL round-bottomed flask was charged with aryl halides (0.5 mmol), arylboronic acid (0.6 mmol), K2CO3 (1.25 mmol), Ni(TFA)2 (0.025 mmol), beta-diketone ligand (0.05 mmol), PPh3 (0.05 mmol), 1.5 g of the ionic liquid (IL) and 0.5 g of H2O. Then, the mixture was stirred at 80 open to the atmosphere. The reaction was monitored by TLC and then stopped after the starting material was completely consumed. Next, the mixture was diluted with water (10 mL) and extracted with ether (310 mL). The combined organic layers were washed with brine (310 mL), dried over MgSO4, and concentrated in vacuum. The cross coupling products were not the only product of the reaction. A small amount of homo-coupled products and removal boron product from boric acids were observed. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate, 10:1).

Reference： [1]Green Chemistry,2009,vol. 11,p. 309 - 313
[2]Beilstein Journal of Organic Chemistry,2011,vol. 7,p. 555 - 564
[3]Catalysis Communications,2014,vol. 58,p. 154 - 157

49
[ 1055880-27-7 ]
[ 3900-89-8 ]
[ 1055880-31-3 ]

Yield	Reaction Conditions	Operation in experiment
82.5%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 95℃; for 12h;Inert atmosphere;	Example 10; 9-(2-chlorophenyl)-2,3,4,5-tetrahydro-1,4-benzoxazepine hydrochloride; (1) tert-butyl 9-(2-chlorophenyl)-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate; A mixture of tert-butyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (200 mg, 0.605 mmol), a solution of <strong>[3900-89-8]2-chlorophenylboronic acid</strong> (143 mg, 0.912 mmol) in ethanol (0.7 ml), 2N aqueous sodium carbonate solution (2.5 ml) and tetrakis(triphenylphosphine)palladium(0) (84.0 mg, 0.0730 mmol) in toluene (5 ml) were stirred under a nitrogen atmosphere at 95°C for 12 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the desired product (180 mg, 82.5percent) as an oil. 1H-NMR (CDCl3) delta; 1.44 (9H, s), 3.75 (2H, br s), 3.96 (2H, br s), 4.47 (2H, br s), 7.05-7.14 (2H, m), 7.19-7.31 (4H, m), 7.44-7.47 (1H, m).

Reference： [1]Patent: EP2123644,2009,A1 .Location in patent: Page/Page column 50

50
[ 445-02-3 ]
[ 3900-89-8 ]
[ 1148126-07-1 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 2683 - 2693

51
[ 3900-89-8 ]
[ 38762-41-3 ]
[ 1148126-06-0 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 2683 - 2693

52
[ 3141-24-0 ]
[ 3900-89-8 ]
[ 1208902-95-7 ]

Reference： [1]Synlett,2009,p. 3311 - 3314

53
[ 615-87-2 ]
[ 3900-89-8 ]
[ 1263048-16-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 3267 - 3274

54
[ 7657-09-2 ]
[ 3900-89-8 ]
[ 1343404-84-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 70℃; for 8h;Inert atmosphere;	General procedure: The reaction was carried out in a pressure tube. To a dioxane suspension (5 mL) of the <strong>[7657-09-2]1,4-dibromo-2-(trifluoromethyl)benzene</strong> (6), Pd(PPh3)4 (3-5 mol%) and of the arylboronic acid (2) was added an aqueous solution of K2CO3 (2 M, 1-2 mL). The mixture was heated at the indicated temperature (70 8C) under Argon atmosphere for the indicated period of time (8 h). The solution was cooled to 20 C, poured into H2O and CH2Cl2 (5 mL each), and the organic and the aqueous layers were separated. The later was extracted with CH2Cl2 (3 15 mL). The combined organic layers were washed with H2O (3 10 mL), dried (Na2SO4), and concentrated in vacuo. The residue was purified by chromatography (flash silica gel, heptanes/EtOAc) to give 4-bromo-3-(trifluoromethyl)biphenyls (7a-o) (79-94%).

Reference： [1]Synlett,2011,p. 1895 - 1899
[2]Journal of Fluorine Chemistry,2013,vol. 145,p. 18 - 34

55
[ 72115-09-4 ]
[ 3900-89-8 ]
[ 1369584-74-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 3923 - 3933

56
[ 109179-31-9 ]
[ 3900-89-8 ]
C₁₄H₁₁ClO [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 3550 - 3553

57
[ 3900-89-8 ]
[ 81190-89-8 ]
[ 1445891-12-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With caesium carbonate; tetrakis(triphenylphosphine)palladium (0); In 1,4-dioxane; water; at 150℃; for 0.666667h;Sealed tube; Microwave irradiation;	Methyl 4-(2-chlorophenyl)-1H-pyrazole-3-carboxylate A mixture of <strong>[81190-89-8]methyl 4-bromo-1H-pyrazole-3-carboxylate</strong> (0.10 g, 0.50 mmol), (2-chlorophenyl)boronic acid (0.39 g, 2.5 mmol), tetrakis(triphenylphosphine)palladium(0) (0.056 g, 0.049 mmol) and cesium carbonate (0.54 g, 1.6 mmol) in 1,4-dioxane (2.6 mL) and water (0.6 mL) was sealed in a vial and subjected to microwave irradiation for 40 min at 150 C. The reaction mixture was diluted with water and extracted with DCM. The organic layer was separated, washed with water, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give methyl 4-(2-chlorophenyl)-1H-pyrazole-3-carboxylate (0.064 g, 60%). LCMS (FA): m/z=236.9 (M+H).

Reference： [1]Patent: US2013/165464,2013,A1 .Location in patent: Paragraph 0979

58
[ 76-09-5 ]
[ 3900-89-8 ]
[ 870195-94-1 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 2806 - 2809
[2]Journal of Organic Chemistry,2018,vol. 83,p. 1842 - 1851

59
[ 1060816-22-9 ]
[ 3900-89-8 ]
ethyl 2-(2-chlorophenyl)-1,3-oxazole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); DavePhos; In toluene; at 110℃; for 20h;Inert atmosphere;	Example 44A Ethyl 2-(2-chlorophenyl)-1,3-oxazole-5-carboxylate Under argon, 300 mg (1.71 mmol) of <strong>[1060816-22-9]ethyl 2-bromo-1,3-oxazole-5-carboxylate</strong> together with 422 mg (2.56 mmol) of 2-chlorophenylboronic acid were dissolved in 7 ml of toluene, and 67 mg (0.17 mmol) of 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl, 78 mg (0.085 mmol) of tris(dibenzylideneacetone)dipalladium and 725 mg (3.42 mmol) of potassium phosphate were added successively. The mixture was heated to 110 C. and stirred at this temperature for 20 h. For work-up, the reaction mixture was allowed to cool to RT and diluted with 20 ml of ethyl acetate and 20 ml of water. After phase separation, the aqueous phase was extracted two more times with in each case 20 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC [Method 19]. This gave 217 mg (50% of theory) of the target compound. LC/MS [Method 3]: Rt=1.21 min; MS [ESIpos]: m/z=252 (M+H)+.

Reference： [1]Patent: US2013/190330,2013,A1 .Location in patent: Paragraph 0453; 0454; 0455

60
[ 51329-15-8 ]
[ 3900-89-8 ]
[ 1332503-64-6 ]
[ 1332503-66-8 ]

Yield	Reaction Conditions	Operation in experiment
43%; 46%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 110℃; for 1h;Inert atmosphere;	Methyl 5-bromo-2'-chlorobiphenyl-3-carboxylate and methyl 2,2"-dichloro-1,1':3',1"-terphenyl-5'-carboxylate Under argon, 60 mg (0.05 mmol) of tetrakis(triphenylphosphine)palladium(0) were added to 300 mg (1.02 mmol) of <strong>[51329-15-8]methyl 3,5-dibromobenzoate</strong> in 6 ml of dioxane. The mixture was heated to 110 C., and 1.0 ml (2.00 mmol) of 2 M aqueous sodium carbonate solution and 239 mg (1.53 mmol) of 2-chlorophenylboronic acid, dissolved in 1 ml of dioxane, were added successively. The mixture was then stirred at 110 C. for 1 h. For work-up, the reaction mixture was allowed to cool to RT and diluted with 20 ml of ethyl acetate and 20 ml of water. After phase separation, the aqueous phase was extracted two more times with in each case 20 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was separated into the components by preparative HPLC [Method 19]. This gave 142 mg (43% of theory) of methyl 5-bromo-2'-chlorobiphenyl-3-carboxylate (Example 113A) and 166 mg (46% of theory) of methyl 2,2"-dichloro-1,1':3',1"-terphenyl-5'-carboxylate (Example 114A) as reaction products. Example 113A GC/MS [Method 20]: Rt=7.50 min; MS [ESIpos]: m/z=324 and 326 (M)+. Example 114A GC/MS [Method 20]: Rt=10.26 min; MS [ESIpos]: m/z=356 and 358 (M)+.

Reference： [1]Patent: US2013/190330,2013,A1 .Location in patent: Paragraph 0669; 0670; 0671; 0672; 0673; 0674

61
[ 3900-89-8 ]
[ 16308-68-2 ]
[ 459-64-3 ]
3-(2-chlorophenyl)-3-(4-methoxyphenyl)propyl phenyl carbonate [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5008 - 5011

62
[ 3900-89-8 ]
[ 611-33-6 ]

Reference： [1]Chinese Chemical Letters,2014,vol. 25,p. 779 - 782

63
[ 1245644-42-1 ]
[ 3900-89-8 ]
6-bromo-3-(2-chlorophenyl)-imidazo[1,2-a]pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33.7%	With palladium diacetate; sodium carbonate; triphenylphosphine; In 1,4-dioxane; water; at 80.0℃; for 18.0h;Inert atmosphere;	General procedure: [0194] <strong>[1245644-42-1]6-bromo-3-iodo-imidazo[1,2-a]pyrazine</strong> 17* (0.648 g, 2 mmol) was added to a degassed mixture of dioxane(10 ml) and water (1.5 ml). The aromatic boronic acid (R2B(OH)2) (2.2 mmol) was added followed by palladium acetate(0.022 g, 5 mol%), triphenyl phosphine (0.025 g, 5 mol%) and sodium carbonate (0.32 g, 3 mmol). The reaction mixturewas stirred at 80 C under nitrogen for 18 hours. The solvent was evaporated in vacuo and the residue was partitionedbetween water (20 ml) and dichloromethane (50 ml). The dichloromethane was separated, dried over magnesium sulphateand evaporated in vacuo. The residue was purified by flash chromatography.

Reference： [1]Patent: EP2818471,2014,A1 .Location in patent: Paragraph 0193; 0194; 0195

64
[ 3900-89-8 ]
[ 39885-50-2 ]
2′-chloro-5′-(trifluoromethyl)-[1,1′-biphenyl]-2-amine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 928 - 941

65
[ 3900-89-8 ]
[ 39885-50-2 ]
[ 2467-83-6 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 928 - 941

66
[ 3900-89-8 ]
[ 245-08-9 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 928 - 941

67
[ 56423-63-3 ]
[ 3900-89-8 ]
2-(2-chlorophenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,4-dioxane; water; at 80℃; for 15h;Sealed tube;	Step A: 2-(2-Chlorophenyl)pyrazine (2508) 2-Bromopyrazine (100 mg, 0.630 mmol) and ((2-chlorophenyl)boronic acid (103 mg, 0.660 mmol) were added to a 5 mL sealable vial equipped with a stir-bar. A solution consisting of 1,4-dioxane (3 mL) and Na2CO3 (1.6 mL, 2 M) was added and the mixture sparged with argon for 10 minutes before adding Pd(ddp)Cl2.CH2Cl2 (23 mg, 0.031 mmol) and heating at 80 Celsius for 15 hours. The reaction was then cooled to rt, diluted with 5 mL of ethyl acetate and 5 mL of water, and the mixture extracted with ethyl acetate (3×20 mL). The combined organic extracts were then dried with sodium sulfate and concentrated to dryness. The resultant residue was subjected to FCC to provide the title compound. 1H NMR (500 MHz, CDCl3) delta 8.98-8.96 (d, J=1.6, 1H), 8.70-8.68 (dd, J=2.5, 1.6, 1H), 8.58-8.56 (d, J=2.6, 1H), 7.66-7.58 (m, 1H), 7.54-7.50 (m, 1H), 7.43-7.39 (m, 2H).

Reference： [1]Patent: US2015/259357,2015,A1 .Location in patent: Paragraph 2508

68
[ 3900-89-8 ]
[ 873-40-5 ]
2,5-dichloro-3-(2-chlorophenyl)pyrazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; sodium hydroxide; In tetrahydrofuran; water; at 40 - 80℃; for 12.0h;Inert atmosphere; Reflux;	General procedure: Under nitrogen gas stream <strong>[873-40-5]2,3,5-trichloropyrazine</strong> of 28g (152.65mmol),2-chlorophenylboronic acid of 23.8g (152.65mmol),Put THF / H2O and K2CO3 of 800ml / 200ml 63.3g (457.9mmol) and stirred. At 40 into the Pd (PPh3) 4 of 5.3g (4.58mmol) was stirred at 80 for 12 hours.After completion of the reaction, which was then extracted with dichloromethane. The organic layer was dried over MgSO4 filtered under reduced pressure. The filtered organic layer was evaporated under reduced pressure to a back by column chromatography the desired compound 2,5-dichloro-3- (2-chlorophenyl) pyrazine 12g (yield: 30%) was obtained.
30%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 40 - 80℃; for 12.0h;Inert atmosphere;	28.5 g (152.65 mmol) of <strong>[873-40-5]2,3,5-trichloropyrazine</strong>, 23.8 g (152.65 mmol) of 2-chlorophenylboronic acid, 63.3 g (457.9 mmol) of K2CO3 and 800 ml / 200 ml of THF/H2O were added under nitrogen atmosphere and stirred. 5.3 g (4.58 mmol) of Pd (PPh3) 4 was added at 40 DEG C, and the mixture was stirred at 80 DEG C for 12 hours. After completion of the reaction, the reaction mixture was extracted with dichloromethane. The organic layer was dried over MgSO4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and 12 g (yield: 30%) of 2,5-dichloro-3- (2-chlorophenyl) pyrazine was obtained by column chromatography.

Reference： [1]Patent: KR101488560,2015,B1 .Location in patent: Paragraph 0109-0112
[2]Patent: KR101920101,2018,B1 .Location in patent: Paragraph 0109-0112

69
[ 55977-10-1 ]
[ 3900-89-8 ]
3-(2-chlorophenyl)-7-hydroxy-4-methyl-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50.2%		A oven dried sealable flask was charged with anhydrous potassium carbonate (9.509 g, 68.8 mmol, 3.0 equiv.), 2-chlorophenylboronic acid (5.380 g, 34.4 mmol, 1.5 equiv.) and tetrakis-triphenylphosphine palladium (0) (1.325 g, 1.1 mmol, 0.1 equiv., 10 mol %) and 100 mL of toluene:EtOH (2:1) and stirred for 5 min at RT. 3-Bromo-7-hydroxy-4-methyl-2H-chromen-2-one (5.850 g, 22.9 mmol, 1.0 equiv.), commercially available, was added and the mixture was heated at 90 C. under nitrogen overnight. The reaction was cooled to ambient temperature and diluted with EA and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated. The resulting residue was dissolved in DCM and loaded to a silica gel column (120 g, 30% EA/Hex, then 1% MeOH/DCM) to give a light brown material which was triturated with MeOH to afford the title compound (3.30 g, 50.2%) as an off-white solid. 1H NMR (300 MHz, CDCl3), delta 10.62 (s, 1H), 7.71 (d, J=9.0 Hz, 1H), 7.60-7.57 (m, 1H), 7.46-7.35 (m, 3H), 6.86 (dd, J=9.0, 2.4 Hz, 1H), 6.78 (d, J=1.8 Hz, 1H), 2.12 (s, 3H).

Reference： [1]Patent: US2016/311805,2016,A1 .Location in patent: Paragraph 0458-0459

70
[ 1435-54-7 ]
[ 3900-89-8 ]
C₁₂H₇BrClF [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane;	Scheme 4-1: In Step 1 the appropriately substituted dibromo species is coupled with an appropriate boronic acid as known in the art to form a mixture of biaryl and triaryl products from which the desired biaryl compound is isolated. In Step 2 the appropriately substituted biaryl species is converted to the Grignard reagent with activated magnesium. In Step 3 the appropriately substituted aldehyde is treated with the previously prepared Grignard reagent to form an alcohol. In Step 4 the appropriately substituted alcohol is converted to a bromide as known in the art with carbon tetrabromide and triphenyl phosphine. In Step 5 the appropriately substituted bromide is converted to the Grignard reagent with activated magnesium.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane;Inert atmosphere;	EXAMPLE 4. SYNTHESIS OF L-B MOIETIES [0503] Scheme 4-1 : In Step 1 the appropriately substituted dibromo species is coupled with an appropriate boronic acid as known in the art to form a mixture of biaryl and triaryl products from which the desired biaryl compound is isolated. In Step 2 the appropriately substituted biaryl species is converted to the Grignard reagent with activated magnesium. In Step 3 the appropriately substituted aldehyde is treated with the previously prepared Grignard reagent to form an alcohol. In Step 4 the appropriately substituted alcohol is converted to a bromide as known in the art with carbon tetrabromide and triphenyl phosphine. In Step 5 the appropriately substituted bromide is converted to the Grignard reagent with activated magnesium.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane;Inert atmosphere;	General procedure: Scheme 4-1: In Step 1 the appropriately substituted dibromo species is coupled with an appropriate boronic acid as known in the art to form a mixture of biaryl and triaryl products from which the desired biaryl compound is isolated. In Step 2 the appropriately substituted biaryl species is converted to the Grignard reagent with activated magnesium. In Step 3 the appropriately substituted aldehyde is treated with the previously prepared Grignard reagent to form an alcohol. In Step 4 the appropriately substituted alcohol is converted to a bromide as known in the art with carbon tetrabromide and triphenyl phosphine. In Step 5 the appropriately substituted bromide is converted to the Grignard reagent with activated magnesium.

	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane;	Scheme 4-1: In Step 1 the appropriately substituted dibromo species is coupled with an appropriate boronic acid as known in the art to form a mixture of biaryl and triaryl products from which the desired biaryl compound is isolated. In Step 2 the appropriately substituted biaryl species is converted to the Grignard reagent with activated magnesium. In Step 3 the appropriately substituted aldehyde is treated with the previously prepared Grignard reagent to form an alcohol. In Step 4 the appropriately substituted alcohol is converted to a bromide as known in the art with carbon tetrabromide and triphenyl phosphine. In Step 5 the appropriately substituted bromide is converted to the Grignard reagent with activated magnesium.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane;	Scheme 4-1: In Step 1 the appropriately substituted dibromo species is coupled with an appropriate boronic acid as known in the art to form a mixture of biaryl and triaryl products from which the desired biaryl compound is isolated. In Step 2 the appropriately substituted biaryl species is converted to the Grignard reagent with activated magnesium. In Step 3 the appropriately substituted aldehyde is treated with the previously prepared Grignard reagent to form an alcohol. In Step 4 the appropriately substituted alcohol is converted to a bromide as known in the art with carbon tetrabromide and triphenyl phosphine. In Step 5 the appropriately substituted bromide is converted to the Grignard reagent with activated magnesium.
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane;	Scheme 4-1: In Step 1 the appropriately substituted dibromo species is coupled with an appropriate boronic acid as known in the art to form a mixture of biaryl and triaryl products fromwhich the desired biaryl compound is isolated. In Step 2 the appropriately substituted biaryl species is converted to the Grignard reagent with activated magnesium. In Step 3 the appropriately substituted aldehyde is treated with the previously prepared Grignard reagent to form an alcohol. In Step 4 the appropriately substituted alcohol is converted to a bromide as known in the art with carbon tetrabromide and triphenyl phosphine. In Step 5 the appropriately substituted bromide isconverted to the Grignard reagent with activated magnesium.

Reference： [1]Patent: WO2017/35411,2017,A1 .Location in patent: Paragraph 0553
[2]Patent: WO2017/35413,2017,A2 .Location in patent: Paragraph 0503
[3]Patent: WO2017/35415,2017,A1 .Location in patent: Paragraph 0566; 0591; 0592
[4]Patent: WO2017/35417,2017,A1 .Location in patent: Paragraph 0563
[5]Patent: WO2018/160891,2018,A1 .Location in patent: Page/Page column 488
[6]Patent: WO2018/160889,2018,A1 .Location in patent: Page/Page column 407

71
[ 57798-00-2 ]
[ 3900-89-8 ]
8-(2-chlorophenyl)quinolin-4(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 89℃; for 0.166667h;	General procedure: To a stirred solution of 8-iodoquinolin-4(1H)-one (5c) (50.0 mg, 0.184 mmol) in dioxane/H2O (3:1) (0.7 mL) at ca. 20 C was added in sequence powdered K2CO3 (50.8 mg, 0.360 mmol), phenylboronic acid (39.5 mg, 0.276 mmol), and then Pd(dppf)Cl2xCH2Cl2 (1.87 mg, 1.25 mol%). The reaction mixture was then immersed into a preheated oil bath and heated at ca. 89 C (reflux) for 5 min until the iodoquinolinone 5c was consumed (by TLC). The reaction mixture was then allowed to cool to ca. 20 C, diluted (CH2Cl2, 15 mL), dried (Na2SO4), filtered and adsorbed onto silica gel. Dry flash chromatography (THF/EtOAc, 50:50) gave the title compound 6a (37.1 mg, 96%) as colorles scubes.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2661 - 2664

72
[ 19128-48-4 ]
[ 3900-89-8 ]
C₁₂H₇Cl₂NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In ethanol; toluene; for 12.0h;Reflux;	2-bromo- 1 -chloro-3-nitrobenzene (56g, 234mmo1), 2-chlorophenylboronic acid (74g, 476mmol), tetrakis(triphenylphosphine)palladium (0) (Pd(PPh3)4) (13g, 1 1.9mmol), 2M cesium carbonate (194g, 596mmoL), toluene (l200mL), and ethanol (300mL) were poured into a flask, and dissolved, and then refluxed for 12 hours. After completion of the reaction, an organic layer was extracted with ethyl acetate. The organic extract was dried on magnesium sulfate, and purified by column chromatography to obtain compound 1-1 (51g, yield: 80percent).

Reference： [1]Patent: WO2017/99360,2017,A1 .Location in patent: Paragraph 176; 177; 178; 179

73
[ 599-66-6 ]
[ 3900-89-8 ]
[ 92023-43-3 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 5521 - 5524

74
[ 920965-87-3 ]
[ 3900-89-8 ]
4-(2-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 8945 - 8962

75
[ 3900-89-8 ]
[ 120157-97-3 ]
2-(2'-chloro-[1,1'-biphenyl]-4-yl)ethan-1-amine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%		General procedure: A mixture of N-boc-2-(4-bromophenyl)ethylamine, the desiredarylboronic acid (a-m) (1.2 equiv), tetrakis(triphenylphosphine)-palladium(0) (0.04 equiv), Na2CO3 (5 equiv) in degassed toluene/H2O (5/2) was refluxed for 18 h. The reaction mixture was filteredthrough Celite and concentrated in vacuo. The resulting residuewas dissolved in in EtOAc (200 mL), washed with H2O (200 mL 2) and brine (200 mL). The organic layer was dried with anhydrousNa2SO4 and concentrated in vacuo. The residue was purified by columnchromatography on SiO2. Using Method E, 13 (1.00?g, 3.3?mmol), 2-chlorophenylboronic acid (0.63?g, 4.0?mmol), tetrakis(triphenylphosphine)palladium(0) (0.15?g, 0.1?mmol) and Na2CO3 (1.77?g, 16.7?mmol) in toluene/H2O (33?ml/13.3?ml), followed by 4.0?M HCl in dioxane (2.50?ml, 10.0?mmol) gave 14f as a white solid (0.47?g, 53%): Rf?=?0.00 (EtOAc 9: acetone 1): 1H NMR (DMSO-d6, 400?MHz) delta 2.90-3.11 (m, NH3CH2CH2), 7.24-7.64 (m, 8 ArH), 8.33 (s, NH3); 13C NMR (DMSO-d6, 100?MHz) delta 33.0 (NCH2CH2), 129.0, 129.7, 136.8, 137.2, 138.0, 162.3 (12 ArC).

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 232 - 244

76
[ 886762-73-8 ]
[ 3900-89-8 ]
2'-chloro-3-fluoro-[1,1'-biphenyl]-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutylammomium bromide; potassium carbonate; In 1,4-dioxane; water; at 130.0℃; for 1h;Microwave irradiation;	General procedure: Substituted 2-iodoaniline 1 (1.0 eq.), substituted phenylboronicacid 2 (1.2 eq.), K2CO3 (3.0 eq.), tetrabutylammonium bromide (0.1eq.), PdCl2(dppf) (0.1 eq.) and dioxane/H2O (9:1) (0.5 M) wereadded to a 10 mL microwave-vial. The vial was sealed with a capand placed in a Cem Discover-microwave cavity. After irradiation at130 C for 1 h and subsequent cooling, the solvent was removed invacuo. The residue was taken up into EtOAc (30 mL) and washedonce withwater and brine. The organic layerwas dried over MgSO4,filtered, and concentrated. The crude product was purified by flashcolumn chromatography using 0e10% EtOAc/petroleum benzine togive the biphenylamine product 3a-3aa.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 148,p. 507 - 518

77
[ 84483-28-3 ]
[ 3900-89-8 ]
2',3-dichloro-[1,1'-biphenyl]-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutylammomium bromide; potassium carbonate; In 1,4-dioxane; water; at 130℃; for 1h;Microwave irradiation;	General procedure: Substituted 2-iodoaniline 1 (1.0 eq.), substituted phenylboronicacid 2 (1.2 eq.), K2CO3 (3.0 eq.), tetrabutylammonium bromide (0.1eq.), PdCl2(dppf) (0.1 eq.) and dioxane/H2O (9:1) (0.5 M) wereadded to a 10 mL microwave-vial. The vial was sealed with a capand placed in a Cem Discover-microwave cavity. After irradiation at130 C for 1 h and subsequent cooling, the solvent was removed invacuo. The residue was taken up into EtOAc (30 mL) and washedonce withwater and brine. The organic layerwas dried over MgSO4,filtered, and concentrated. The crude product was purified by flashcolumn chromatography using 0e10% EtOAc/petroleum benzine togive the biphenylamine product 3a-3aa.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 148,p. 507 - 518

78
[ 461-89-2 ]
[ 3900-89-8 ]
2-(2-chlorophenyl)-1,2,4-triazine-3,5(2H,4H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With oxygen; copper diacetate; triethylamine; In N,N-dimethyl-formamide; at 65℃; for 4h;	General procedure: To a solution of <strong>[461-89-2]6-azauracil</strong> (100 mg, 0.88 mmol) inDMF (10.0 mL) was added base (1.76 mmol) and Cu(OAc) 2(159 mg, 0.88 mmol) at room temperature. The resulting reationmixture was degassed with oxygen for 10 min and then addedarylboronic acids (0.96 mmol) at room temperature and stirredat appropriate temperature (Table-1) under oxygen atmosphere.The reaction mixture was diluted with water (15 mL) andextracted with dichloromethane (3 × 15 mL). The organic layerwashed with H 2 O (15 mL), brine solution (15 mL), dried overNa 2 SO 4 and concentrated. The obtained crude product waspurified by column chromatography (0 to 10 % CH 3 OH/CH 2 Cl 2 )to afford the title compounds.

Reference： [1]Asian Journal of Chemistry,2018,vol. 30,p. 2495 - 2501

79
[ 3900-89-8 ]
[ 87376-25-8 ]
(2-amino-4-nitrophenyl)(2-chlorophenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With 4,4'-bipyridine; methanesulfonic acid; palladium diacetate; In tetrahydrofuran; water; at 80℃; for 13.0h;Inert atmosphere;	Pd(OAc)2 (138 mg, 0.614 mmol), Bipy (143 mg, 0.92 mmol), <strong>[87376-25-8]2-amino-4-nitrobenzonitrile</strong> (2.00 g, 12.27 mmol), (2-chlorophenyl)boronic acid (3.80 g, 24.54 mmol) and MsOH (8 mL, 123 mmol) were dissolved in 45 mL of THF/H2O : 2/1 and stirred for 13h at 80C under nitrogen. The reaction mixture was diluted with EtOAc and an aqueous saturated solution of NaHCO3. The organic layer was separated, washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by Combiflash silica gel chromatography (0-70% of EtOAc in hexane), which provided 2.60 g (77%) of the title compound as a colorless solid. MS (ESI+) m/z: 277.6 [M+H+].

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3210 - 3215

80
[ 98027-84-0 ]
[ 1220220-21-2 ]
[ 3900-89-8 ]
N-[4-[2-(2-chlorophenyl)-6-oxo-1H-pyridin-4-yl]-2-pyridyl]acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6 mg		2,6-Dichloro-4-iodo-pyridine (0.5 g, 1 .83 mmol), N-[4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)-2-pyridyl]acetamide (0.53 g, 2.01 mmol), K2CO3(0.5 g, 3.65 mmol) and PdCI2(dppf) (0.07 g, 0.09 mmol) were dissolved in DME (3 ml) and water (1 ml) and the mixture was stirred at 80 C for 1 h. (2- Chlorophenyl)boronic acid (0.29 g, 1 .83 mmol), K2CO3(0.5 g, 3.65 mmol) and PdCl2(dppf) (0.07 g, 0.09 mmol) were added and the mixture was stirred for 4 h at 100 C. The organic layer was separated, filtered and concentrated. The crude material was taken up in toluene (4 ml), KOtBu (0.141 g, 1 .26 mmol) was added and the mixture stirred at 100 C for 30 min. When cooled to rt the mixture was concentrated, dissolved in MeOH/DMF, filtered and purified by preparative HPLC to give the product as a solid (6 mg, 4%).1H NMR (500 MHz, METHANOL-^) delta ppm 1 .92 (s, 1 H) 2.22 (s, 3 H) 6.75 (s, 1 H) 6.87 (s, 1 H) 7.43 (dd, 1 H) 7.46 - 7.52 (m, 1 H) 7.55 (td, 1 H) 7.57 - 7.67 (m, 2 H) 8.39 - 8.53 (m, 2 H). MS ES+ m/z 341 [M+H]+.

Reference： [1]Patent: WO2019/38387,2019,A1 .Location in patent: Page/Page column 30

81
[ 161833-42-7 ]
[ 3900-89-8 ]
C₂₀H₁₆ClN₃OS [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 1407 - 1412

82
[ 161833-42-7 ]
[ 3900-89-8 ]
[ 137102-30-8 ]
C₂₄H₂₆ClN₃O₃S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 1407 - 1412

83
[ 188875-37-8 ]
[ 3900-89-8 ]
[ 215453-51-3 ]
C₂₈H₂₈ClN₃O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 1407 - 1412

84
[ 188875-37-8 ]
[ 3900-89-8 ]
[ 215453-51-3 ]
C₂₃H₂₀ClN₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 1407 - 1412

85
[ 3900-89-8 ]
[ 3921-01-5 ]
C₁₀H₆BrClN₂ [ No CAS ]

Reference： [1]Journal of Pharmacology and Experimental Therapeutics,2019,vol. 370,p. 514 - 527

86
[ 1885-32-1 ]
[ 3900-89-8 ]
2-(2-chlorophenyl)-8-methyl-2,3-dihydrobenzo[d][1,3,2]diazaborinin-4(1H)-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 5018 - 5024

87
[ 3900-89-8 ]
[ 114897-91-5 ]
(±)-4-((4-((2'-chloro-3-fluoro-[1,1'-biphenyl]-4-yl)(cyano)methyl)pyrimidin-2-yl)amino)benzonitrile [ No CAS ]

Reference： [1]Molecules,2020,vol. 25

88
[ 3900-89-8 ]
[ 114897-91-5 ]
C₁₄H₉ClFN [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; palladium dichloride; In water; at 25℃;	General procedure: A mixture of arylboronic acids 3a-n (5.5 mmol, 1.1 equiv.), dierent substituted 2-(4-bromophenyl)acetonitriles 4a-c (5.0 mmol, 1.0 equiv.), PdCl2 (0.025 mmol, 0.005 equiv.), K2CO3 (17.5 mmol, 3.5 equiv.),PEG400 15 mL, and H2O 15 mL were added to a 100-mL round-bottom flask, and stirred at roomtemperature for the desired time until complete consumption of starting material as judged by TLC.Then, the reaction mixture was poured into water (100 mL) and extracted with ethyl acetate (30 mL x 3). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered,and removed by evaporation under reduced pressure to aord the crude products, which were furtherpurified by column chromatography on silica gel eluting with EtOAc/petroleum ether to 5a-p aswhite solid.

Reference： [1]Molecules,2020,vol. 25

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Precautionary Statements-General
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Prevention
Code	Phrase
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P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
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P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
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
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
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.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
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:
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P401
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
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H221	Flammable gas
H222	Extremely flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 3900-89-8 ] {[proInfo.proName]}

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[ 3900-89-8 ] Synthesis Path-Upstream 1~12

[ 3900-89-8 ] Synthesis Path-Downstream 1~88

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Organoboron

Aryls

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