[ CAS No. 175883-62-2 ] {[proInfo.proName]}

Name: 175883-62-2|4-Methoxy-3-methylphenylboronic acid|98%
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SKU: A141652
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2D 3D

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Quality Control of [ 175883-62-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 175883-62-2 ]

Product Details of [ 175883-62-2 ]

CAS No. :	175883-62-2	MDL No. :	MFCD02179464
Formula :	C₈H₁₁BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PXVDQGVAZBTFIB-UHFFFAOYSA-N
M.W :	165.98	Pubchem ID :	2773487
Synonyms :

Calculated chemistry of [ 175883-62-2 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	47.73
TPSA :	49.69 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) :	-6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.16
Log Po/w (WLOGP) :	-0.32
Log Po/w (MLOGP) :	0.33
Log Po/w (SILICOS-IT) :	-0.3
Consensus Log Po/w :	0.17

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	2.41 mg/ml ; 0.0145 mol/l
Class :	Very soluble
Log S (Ali) :	-1.8
Solubility :	2.64 mg/ml ; 0.0159 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.79
Solubility :	2.66 mg/ml ; 0.016 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.58

Safety of [ 175883-62-2 ]

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 [ 175883-62-2 ]

* 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 [ 175883-62-2 ]
Downstream synthetic route of [ 175883-62-2 ]

[ 175883-62-2 ] Synthesis Path-Upstream 1~2

1
[ 14804-31-0 ]
[ 175883-62-2 ]

Reference： [1] Journal of the American Chemical Society, 2003, vol. 125, # 36, p. 10977 - 10996
[2] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 6, p. 588 - 598
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2324 - 2341

2
[ 117896-10-3 ]
[ 175883-62-2 ]

Reference： [1] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 6, p. 588 - 598

[ 175883-62-2 ] Synthesis Path-Downstream 1~88

1
[ 14371-10-9 ]
[ 175883-62-2 ]
C₁₇H₁₈O₂ [ No CAS ]
C₁₇H₁₈O₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 4007 - 4010

2
[ 175883-62-2 ]
[ 504-63-2 ]
C₁₁H₁₄BBrO₃ [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 5125 - 5129

3
[ 950180-17-3 ]
[ 175883-62-2 ]
C₂₇H₃₀ClNO₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5233 - 5238

4
C₁₇H₂₀INO₃S [ No CAS ]
[ 175883-62-2 ]
C₂₅H₂₉NO₄S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5233 - 5238

5
[ 868262-22-0 ]
[ 175883-62-2 ]
C₂₈H₃₃NO₅S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5233 - 5238

6
[ 175883-62-2 ]
N,N'-4,4'-bis(benzyl-6-methoxy-3-boronic acid)-bipyridinium dibromide [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 5125 - 5129

7
[ 175883-62-2 ]
[ 460748-07-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2559 - 2563

8
[ 175883-62-2 ]
4-(7-methyl-2-{2-[(2R)-2-methyl-1-pyrrolidinyl]ethyl}-1-benzofuran-5-yl)benzonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2559 - 2563

9
[ 175883-62-2 ]
[ 460748-08-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 2559 - 2563

10
[ 175883-62-2 ]
3'-methyl-3-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-biphenyl-4,4'-diol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 10977 - 10996

11
[ 175883-62-2 ]
4,4'-bis-allyloxy-3'-methyl-3-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-biphenyl [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 10977 - 10996

12
[ 175883-62-2 ]
3-[4'-(2,3-dihydroxypropyloxy)-3-(1H,1H,2H,2H,3H,3H-perfluorononyl)-3'-methylbiphenyl-4-yloxy]propane-1,2-diol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2003,vol. 125,p. 10977 - 10996

13
[ 175883-62-2 ]
5,6-Bis(4-hydroxy-3-methylphenyl)acenaphthene [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 1 (2001),2001,p. 588 - 598

14
[2-(4-bromo-2-isobutylphenoxy)ethyl]-methylamino}-acetic acid tert-butyl ester [ No CAS ]
[ 175883-62-2 ]
[2-(3-isobutyl-4'-methoxy-3'-methylbiphenyl-4-yloxy)ethyl]-methylamino}-acetic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		Dissolve f [2-(4-bromo-2-isobutylphenoxy)ethyl]-methylamino}-acetic acid tert- butyl ester (2 g, 4.99 mmol) in dry tetrahydrofuran (20 mL). Deliver an aliquot of this stock solution (4 mL, 0.999 mmol) under nitrogen to a solution in tetrahydrofuran (5 mL) of the appropriate arylboronic acid (1.5 eq), palladium acetate (22 mg, 0.1 eq; 0.099 mmol), tricyclohexylphosphine (34 mg, 0.12 eq; 0.1198 mmol) and potassium fluoride (180 mg, 3.1 eq; 3.098 mmol). Stir at reflux for 66 h. Monitor the progress of the reactions after 66 h and treat each reaction then individually as described. Deliver an aliquot of [2-(4-bromo-2-isobutylphenoxy)ethyl]-methylamino)-acetic acid tert-butyl ester (0.999 mmol of the stock solution), along with (4-methoxy-3-methyl) boronic acid (248 mg, 1.4939 mmol, 95% pure), palladium acetate (22 mg), tricyclohexylphosphine (34 mg, 0.12 eq; 0.1214 mmol) and potassium fluoride (180 mg, 3.098 mrnol). Add a second aliquot of reagents after 66 h (4-methoxy-3-methyl) boronic acid (248 mg, 1.4939 mmol), tricyclohexylphosphine (37 mg, 0.1319 mmol), palladium acetate (24 mg) and potassium fluoride (186 mg, 3.20 mmol). Stir for another 24 h. Dilute with tetrahydrofuran (dry, 4 mL) and treat with [1,1'-bis(diphenylphosphino)-ferrocene)- dichloropalladium (II) complex (DPPF) (76 mg, 0.093 eq), 2 N aqueous potassium carbonateaq (5 eq, 2.5 mL) and (4-methoxy-3-methyl) boronic acid (166 mg) and stir at reflux for 24 h until total consumption of the starting material as indicated by thin layer chromatography and LC-MS. Filter the crude reaction mixture through a -wet CeliteNo. pad, dilute with ethyl acetate (50 mL), wash the organic, phase with water (50 mL), dry (magnesium sulfate), filter, concentrate and purify (HPLC, eluting with 10:90 ethyl acetate: hexanes) to give the title compound (302.8 mg, 62%). ¹H NMR (400 MHz, CDC13) 8 7.36-7.32 (m, 3H), 7.28-7.27 (m, 1H), 6.8 8 (d, J = 8.3 Hz, 2H), 4.13 (m, 2H), 3.87 (s, 3H), 3.36 (s, 2H), 3.05 (t, J =.5.7 Hz, 2H), 2.55-2.53 (m, 5H), 2.29 (s, 3H), 1.96 (q, J = 6.6 Hz, 1H, ), 1.49 (s, 9H), 0.94 (d, J = 6.6 Hz, 6H,); LC-MS: mz = 442.0

Reference： [1]Patent: WO2005/100301,2005,A1 .Location in patent: Page/Page column 107-108

15
[ 619-58-9 ]
[ 175883-62-2 ]
[ 71-36-3 ]
[ 885965-61-7 ]

Yield	Reaction Conditions	Operation in experiment
30%	With caesium carbonate;tetrakis(triphenylphosphine)palladium (0); In water; ethyl acetate; toluene;	Step 1: 3-Methyl-4-methoxyphenylboronic acid (542 mg) was combined with 4-iodobenzoic acid (810 mg), cesium carbonate (5.32 g), toluene (16 mL), water (8 mL) and n-butanol (4 mL). The mixture was degassed under vacuum with argon purging after which, tetrakis-triphenylphosphine palladium (38 mg) was added. The reaction was heated to 80 C. for 20 hours after which, it was cooled to room temperature and diluted with ethyl acetate (16 mL). The layers were separated and the organics were concentrated to dryness. The residue was purified on silica gel (50% to 100% ethyl acetate/hexane over 40 minutes) giving 3'-methyl-4'-methoxy-4-biphenylcarboxylic acid (240 mg). Yield=30%

Reference： [1]Patent: US2003/153556,2003,A1

16
[ 15231-91-1 ]
[ 175883-62-2 ]
[ 550998-12-4 ]

Yield	Reaction Conditions	Operation in experiment
1.56 g (73%)		6-(4-Methoxy-2-methylphenyl)-2-naphthol The title compound was prepared by reacting 6-bromo-2-naphthol (1.8 g, 5.4 mmol) with <strong>[175883-62-2]4-methoxy-3-methylphenylboronic acid</strong> (1.74 g, 7.0 mmol) according to method A to yield 1.56 g (73%) of yellowish solid: mp 124-126 C.; 1H NMR (DMDO-d6): delta 2.25(3H,s), 3.78 (3H, s), 6.85 (1H, dd, J=8.35 Hz, J=2.56 Hz), 6.90 (1H, d, J=2.37 Hz), 7.09 (1H, dd, J=8.75 Hz, J=2.25 Hz), 7.13 (1H, s), 7.20 (1H, d, J=8.33 Hz), 7.35 (1H, dd, J=8.39 Hz, J=1.37 Hz), 7.67 (1H,s), 7.70 (1H, d, J=8.53 Hz), 7.78 (1H, d, J=8.78 Hz), 9.74 (1H, s); MS (ESI) m/z263 (M-H)-. Anal. for C18H16O2: Calc'd: C: 81.79H: 6.10 Found: C: 81.43H: 6.01

Reference： [1]Patent: US2003/181519,2003,A1

17
[ 1028331-34-1 ]
[ 175883-62-2 ]
[ 1028424-71-6 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 2738 - 2742

18
[ 1028424-64-7 ]
[ 175883-62-2 ]
[ 1028424-66-9 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 2738 - 2742

19
[ 175883-62-2 ]
[ 850364-08-8 ]
[ 1056265-63-4 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine;copper diacetate; In dichloromethane; for 41h;Molecular sieve;	Description 34; 1 -[3-Methyl-4-(methyloxy)phenyl]-4-[(phenylmethyl)oxy]-1 H-indazole (D34)The 4-[(phenylmethyl)oxy]-1 H-indazole (D1) (500 mg, 2.23 mmol), the [3-methyl-4- (methyloxy)phenyl]boronic acid (740 mg, 4.46 mmol), copper (II) acetate (608 mg, 3.345 mmol), pyridine (0.36 mL, 4.46 mmol) and powdered molecular sieves (400 mg) in DCM (75 mL) were stirred at room temperature in the presence of air. After 41 hours the mixture <n="34"/>was filtered through a pad of celite and washed with water. The aqueous was re-extracted with DCM and the combined organics were washed with brine and dried over MgSO4. The crude (1.17 g) was purified by flash chromatography (Biotage SP4) with a gradient of EtOAc 0 to 30% in hexane to afford 562 mg of title compound (D34) containing an impurity. LC-MS: MH+ = 345 (C22H20N2O2 = 344)

Reference： [1]Patent: WO2008/107455,2008,A1 .Location in patent: Page/Page column 32-33

20
[ 1052271-60-9 ]
[ 175883-62-2 ]
[ 1059098-72-4 ]

Yield	Reaction Conditions	Operation in experiment
17%	With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 24h;Heating / reflux;	Example 24; 8-(4-methoxy-3-methyl phenyl)H-imidazo[1,5-a]pyridine8-bromo-H-imidazo[1,5-a]pyridine (0.1 g, 0.5 mmol, 1 eq) was dissolved in 10 mL of DME and kept under an argon atmosphere. To that solution [Pd(PPh3)4] (0.025 mmol, 0.05 eq), 4-methoxy-3-methylphenyl boronic acid (0.124 g, 0.75 mmol, 1.5 eq) and an aqueous NaOH solution (0.2M, 5 mL) were added under stirring. The resulting mixture was refluxed for 24 h. After cooling, the mixture was diluted with water and the aqueous layer was extracted with CHCl3. The organic layers were dried (Na2SO4), filtered and evaporated under reduced pressure. Semi-preparative HPLC-chromatography afforded the pure product.Yield: 0.020 g (17%), 1H-NMR, 500 MHz, CDCl3: delta 2.29 (s, 3H); 3.90 (s, 3H); 6.94-6.96 (m, 1H); 7.08-7.10 (m, 2H); 7.35 (s, 1H); 7.39-7.41) m, 1H); 7.88 (s, 1H); 8.29 (bs, 1H); 9.52 (bs, 1H), MS: m/z 239.2 [M+H]+; HPLC: Method [B], (214 nm), rt: 6.68 min (88.3%)

Reference： [1]Patent: US2008/234313,2008,A1 .Location in patent: Page/Page column 31-32

21
[ 107346-32-7 ]
[ 175883-62-2 ]
4-amino-8-(4-methoxy-3-methyl-phenyl)-N-propyl-cinnoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%		EXAMPLE 73 4-amino-8-(4-methoxy-3-methyl-phenyl)-N-propyl-cinnoline-3-carboxamide Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (125 mg, 0.40 mmol) and <strong>[175883-62-2](4-methoxy-3-methylphenyl)boronic acid</strong> (133 mg, 0.80 mmol) were reacted to afford the title compound (105 mg, 75% yield) as a white solid. 1H NMR (300 MHz, CDCl3) delta 8.59 (bs, 1H), 7.76-7.82 (m, 2H), 7.67-7.72 (m, 1H), 7.53 (dd, J=8.2, 2.2 Hz, 1H), 7.46 (m, 1H), 6.96 (d, J=8.2, 1H), 3.89 (s, 3H), 3.46 (apparent q, J=6.7 Hz, 2H), 2.30 (s, 3H), 1.67 (apparent sextet, J=7.2 Hz, 2H), 1.00 (t, J=7.4 Hz, 3H). MS APCI, m/z=351 (M+H) HPLC 1.88 min.

Reference： [1]Patent: US2008/318925,2008,A1

22
[ 122775-34-2 ]
[ 175883-62-2 ]
C₁₇H₁₄O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 275 - 278

23
[ 175883-62-2 ]
[ 219838-95-6 ]
C₁₅H₂₀O₄ [ No CAS ]
C₁₅H₂₀O₄ [ No CAS ]
[ 1155875-37-8 ]

Reference： [1]Synthesis,2009,p. 853 - 859

24
[ 175883-62-2 ]
[ 219838-95-6 ]
C₁₂H₁₆O₂ [ No CAS ]
2-(4-methoxy-3-methylphenyl)but-3-en-1-ol [ No CAS ]
[ 1155875-52-7 ]

Reference： [1]Synthesis,2009,p. 853 - 859

25
[ 1078734-22-1 ]
[ 175883-62-2 ]
[ 1193525-72-2 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6724 - 6743

26
[ 1078734-00-5 ]
[ 175883-62-2 ]
[ 1193525-75-5 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6724 - 6743

27
[ 1078734-14-1 ]
[ 175883-62-2 ]
[ 1193525-42-6 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6724 - 6743

28
[ 74447-69-1 ]
[ 175883-62-2 ]
[ 1193525-78-8 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6724 - 6743

29
[ 1669-43-8 ]
[ 175883-62-2 ]
(R)-4-(4-methoxy-3-methylphenyl)-5-methylhexan-2-one [ No CAS ]
[ 1201810-98-1 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 172 - 175

30
[ 175883-62-2 ]
[ 188637-54-9 ]
trans-2-(4'-methoxy-3'-methylphenyl)-cyclopent-3-enol [ No CAS ]
trans-4-(4'-methoxy-3'-methylphenyl)-cyclopent-2-enol [ No CAS ]
trans-2-(4'-methoxy-3'-methylphenyl)-cyclopent-3-enol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 4056 - 4068

31
[ 175883-62-2 ]
[ 188637-54-9 ]
trans-2-(4'-methoxy-3'-methylphenyl)-cyclopent-3-enyl ethyl carbonate [ No CAS ]
trans-4-(4'-methoxy-3'-methylphenyl)-cyclopent-2-enyl ethyl carbonate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 4056 - 4068

32
[ 175883-62-2 ]
[ 188637-54-9 ]
trans-4-(4'-methoxy-3'-methylphenyl)-cyclopent-2-enol [ No CAS ]
trans-2-(4'-methoxy-3'-methylphenyl)-cyclopent-3-enol [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 4056 - 4068

33
[ 175883-62-2 ]
[ 188637-54-9 ]
trans-4-(4'-methoxy-3'-methylphenyl)-cyclopent-2-enyl ethyl carbonate [ No CAS ]
trans-2-(4'-methoxy-3'-methylphenyl)-cyclopent-3-enyl ethyl carbonate [ No CAS ]
trans-2-(4'-methoxy-3'-methylphenyl)-cyclopent-3-enyl ethyl carbonate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 4056 - 4068

34
[ 557-21-1 ]
[ 175883-62-2 ]
[ 53078-71-0 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 11389 - 11391

35
[ 89937-77-9 ]
[ 175883-62-2 ]
[ 1245425-94-8 ]

Yield	Reaction Conditions	Operation in experiment
36.4%	With pyridine; copper diacetate; triethylamine; In dichloromethane; at 20℃;Molecular sieve;	A. Methyl l-(4-methoxy-3-methylphenyl)-2-oxo-l,2-dihydropyridine-4- carboxylate[00104] To a solution of Part A of Procedure 1 (2.37 g, 15.48 mmol) in CH2Cl2 (20 mL) was added <strong>[175883-62-2]4-methoxy-3-methylphenylboronic acid</strong> (3.85 g, 23.21 mmol), copper (II) acetate (4.22 g, 23.21 mmol), Et3N (4.31 mL, 31.0 mmol), pyridine (2.50 mL, 31.0 mmol) and Molecular Sieves (4 A, 1.5 g). The mixture was stirred at RT overnight and then filtered through Celite. After rinsing the filter cake with 1/1 CH2Cl2/Me0H (200 mL), the combined filtrates were evaporated. Chromatography (silica gel 230-400 mesh, solvent gradient 0-50% EtO Ac/Hex followed by 20% MeOH/CH2Cl2) afforded 2A (1.54 g, 5.64 mmol, 36.4 % yield) as a yellowish solid. LC-MS, [M + H]+ = 274.

Reference： [1]Patent: WO2010/104830,2010,A1 .Location in patent: Page/Page column 75

36
[ 17135-74-9 ]
[ 175883-62-2 ]
[ 1246218-78-9 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 6653 - 6659

37
[ 1262121-51-6 ]
[ 175883-62-2 ]
[ 1262121-63-0 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 5781 - 5791

38
[ 1249181-52-9 ]
[ 175883-62-2 ]
[ 1255940-18-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; for 2h;Inert atmosphere; Reflux;	r5-(4-Methoxy-3-methylphenvn-2-thienyl1(3-methoxyphenyl)methanone (14a). The title compound was prepared by reaction of (5-bromo-2-thienyl)(3- methoxyphenyl)methanone (4b) (200 mg, 0.67 mmol), 4-methoxy-3- methylbenzene boronic acid (133 mg, 0.80 mmol), caesium carbonate (873 mg, 2.68 mmol) and tetrakis(triphenylphosphine) palladium (8 mg, 7 muetaiotaomicronIota) according to method Bl . The product was purified by CC (hexane/ethyl acetate 9 : 1); yield : 79 % (180 mg); NMR (CD3COCD3) : 7.68 (d, J= 4.1 Hz, 1H), 7.64-7.60 (m, 2H), 7.48 (t, J= 7.8 Hz, 1H), 7.46-7.43 (m, 2H), 7.37-7.36 (m, 1H), 7.21 (ddd, J= 1.3 Hz and J= 2.5 Hz and J= 7.9 Hz, 1H), 7.02 (d, J= 8.2 Hz, 1H), 3.90 (s, 3H), 3.89 (s, 3H), 2.24 (s, 3H); 13C NMR (CD3COCD3) : 188.55, 161.70, 160.85, 155.20, 142.90, 141.50, 138.20, 131.45, 130.25, 129.10, 127.35, 127.05, 125.00, 123.00,50, 56.95, 56.80, 17.25.

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 8176 - 8186
[2]Patent: WO2012/25638,2012,A1 .Location in patent: Page/Page column 57-58

39
[ 1255940-23-8 ]
[ 175883-62-2 ]
[ 1255940-24-9 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 8176 - 8186

40
[ 1255940-26-1 ]
[ 175883-62-2 ]
[ 1255940-27-2 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 8176 - 8186

41
[ 1255940-29-4 ]
[ 175883-62-2 ]
[ 1255940-30-7 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 8176 - 8186

42
[ 1255940-31-8 ]
[ 175883-62-2 ]
[ 1255940-32-9 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 8176 - 8186
[2]Patent: WO2012/25638,2012,A1 .Location in patent: Page/Page column 68

43
C₁₁H₄BrClF₃O₃Pol [ No CAS ]
[ 175883-62-2 ]
C₁₉H₁₃ClF₃O₄Pol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 993 - 996

44
[ 1285505-77-2 ]
[ 175883-62-2 ]
[ 1285506-57-1 ]

Yield	Reaction Conditions	Operation in experiment
73.5%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; for 2h;	Example 61Synthesis of N-[(E)-3-(4'-hydroxy-3'-methyl-biphenyl-2-yl)-2-methyl-acryloyl]-guanidine<Step 1>Intermediate 1 (50 mg, 0.126 mmol) and 3-methyl-4-methoxyphenyl boronic acid (23.9 mg, 0.139 mmol) were dissolved in a mixed solution of dioxane and water (v/v=3/1, 2.0 mL). Pd(PPh3)4 (6.94 mg, 6.00 mumol) and Na2CO3 (41.6 mg, 0.378 mmol) were added to the solution and then stirred at 90 C. for 2 hours. After cooling it to room temperature, the solvent was eliminated in vacuo and then purified by reversed phase HPLC (0.1% TFA in water/CH3CN) to obtain the objective coupling product (40.5 mg, 73.5%).MS: 324

Reference： [1]Patent: US2011/82109,2011,A1 .Location in patent: Page/Page column 31

45
[ 1313375-73-3 ]
[ 175883-62-2 ]
[ 1313375-58-4 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5144 - 5153

46
[ 1312996-56-7 ]
[ 175883-62-2 ]
[ 1312996-58-9 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4977 - 4986

47
[ 1268826-55-6 ]
[ 175883-62-2 ]
[ 1340482-07-6 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7547 - 7557

48
[ 1268826-55-6 ]
[ 175883-62-2 ]
[ 1340482-29-2 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 7547 - 7557

49
[ 1352545-12-0 ]
[ 175883-62-2 ]
[ 1352545-26-6 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 475 - 488

50
[ 151239-47-3 ]
[ 175883-62-2 ]
[ 1357563-62-2 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;	General procedure: A mixture of arylbromide (1 equiv), boronic acid (1.2 equiv), cesium carbonate (4 equiv), and tetrakis(triphenylphosphine) palladium (0.02 equiv) was suspended in a DME/water (2:1) solution and the mixture was degazed. The mixture was heated to 80 C and stirred overnight at 80 C under nitrogen. The reaction mixture was cooled to room temperature, quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The product was purified by column chromatography or by recrystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 1 - 17

51
[ 750633-66-0 ]
[ 175883-62-2 ]
[ 1357563-58-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;	General procedure: A mixture of arylbromide (1 equiv), boronic acid (1.2 equiv), cesium carbonate (4 equiv), and tetrakis(triphenylphosphine) palladium (0.02 equiv) was suspended in a DME/water (2:1) solution and the mixture was degazed. The mixture was heated to 80 C and stirred overnight at 80 C under nitrogen. The reaction mixture was cooled to room temperature, quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The product was purified by column chromatography or by recrystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 1 - 17

52
[ 1012043-34-3 ]
[ 175883-62-2 ]
[ 1357564-10-3 ]

Yield	Reaction Conditions	Operation in experiment
92%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;	General procedure: A mixture of arylbromide (1 equiv), boronic acid (1.2 equiv), cesium carbonate (4 equiv), and tetrakis(triphenylphosphine) palladium (0.02 equiv) was suspended in a DME/water (2:1) solution and the mixture was degazed. The mixture was heated to 80 C and stirred overnight at 80 C under nitrogen. The reaction mixture was cooled to room temperature, quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The product was purified by column chromatography or by recrystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 1 - 17

53
[ 1357564-33-0 ]
[ 175883-62-2 ]
[ 1357564-35-2 ]

Yield	Reaction Conditions	Operation in experiment
68%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;	General procedure: A mixture of arylbromide (1 equiv), boronic acid (1.2 equiv), cesium carbonate (4 equiv), and tetrakis(triphenylphosphine) palladium (0.02 equiv) was suspended in a DME/water (2:1) solution and the mixture was degazed. The mixture was heated to 80 C and stirred overnight at 80 C under nitrogen. The reaction mixture was cooled to room temperature, quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The product was purified by column chromatography or by recrystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 1 - 17

54
[ 1357564-39-6 ]
[ 175883-62-2 ]
[ 1357564-41-0 ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;	General procedure: A mixture of arylbromide (1 equiv), boronic acid (1.2 equiv), cesium carbonate (4 equiv), and tetrakis(triphenylphosphine) palladium (0.02 equiv) was suspended in a DME/water (2:1) solution and the mixture was degazed. The mixture was heated to 80 C and stirred overnight at 80 C under nitrogen. The reaction mixture was cooled to room temperature, quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The product was purified by column chromatography or by recrystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 1 - 17

55
[ 1332345-45-5 ]
[ 175883-62-2 ]
[ 1357563-75-7 ]

Yield	Reaction Conditions	Operation in experiment
61%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;	General procedure: A mixture of arylbromide (1 equiv), boronic acid (1.2 equiv), cesium carbonate (4 equiv), and tetrakis(triphenylphosphine) palladium (0.02 equiv) was suspended in a DME/water (2:1) solution and the mixture was degazed. The mixture was heated to 80 C and stirred overnight at 80 C under nitrogen. The reaction mixture was cooled to room temperature, quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The product was purified by column chromatography or by recrystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 1 - 17

56
[ 1357563-81-5 ]
[ 175883-62-2 ]
[ 1357563-83-7 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;	General procedure: A mixture of arylbromide (1 equiv), boronic acid (1.2 equiv), cesium carbonate (4 equiv), and tetrakis(triphenylphosphine) palladium (0.02 equiv) was suspended in a DME/water (2:1) solution and the mixture was degazed. The mixture was heated to 80 C and stirred overnight at 80 C under nitrogen. The reaction mixture was cooled to room temperature, quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The product was purified by column chromatography or by recrystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 1 - 17

57
[ 844878-99-5 ]
[ 175883-62-2 ]
[ 1357563-87-1 ]

Yield	Reaction Conditions	Operation in experiment
157 mg	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;	General procedure: A mixture of arylbromide (1 equiv), boronic acid (1.2 equiv), cesium carbonate (4 equiv), and tetrakis(triphenylphosphine) palladium (0.02 equiv) was suspended in a DME/water (2:1) solution and the mixture was degazed. The mixture was heated to 80 C and stirred overnight at 80 C under nitrogen. The reaction mixture was cooled to room temperature, quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The product was purified by column chromatography or by recrystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 1 - 17

58
[ 1357563-90-6 ]
[ 175883-62-2 ]
[ 1357563-92-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;	General procedure: A mixture of arylbromide (1 equiv), boronic acid (1.2 equiv), cesium carbonate (4 equiv), and tetrakis(triphenylphosphine) palladium (0.02 equiv) was suspended in a DME/water (2:1) solution and the mixture was degazed. The mixture was heated to 80 C and stirred overnight at 80 C under nitrogen. The reaction mixture was cooled to room temperature, quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The product was purified by column chromatography or by recrystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 1 - 17

59
[ 1357563-96-2 ]
[ 175883-62-2 ]
[ 1357563-97-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;	General procedure: A mixture of arylbromide (1 equiv), boronic acid (1.2 equiv), cesium carbonate (4 equiv), and tetrakis(triphenylphosphine) palladium (0.02 equiv) was suspended in a DME/water (2:1) solution and the mixture was degazed. The mixture was heated to 80 C and stirred overnight at 80 C under nitrogen. The reaction mixture was cooled to room temperature, quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The product was purified by column chromatography or by recrystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 1 - 17

60
[ 1357564-01-2 ]
[ 175883-62-2 ]
[ 1357564-03-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;	General procedure: A mixture of arylbromide (1 equiv), boronic acid (1.2 equiv), cesium carbonate (4 equiv), and tetrakis(triphenylphosphine) palladium (0.02 equiv) was suspended in a DME/water (2:1) solution and the mixture was degazed. The mixture was heated to 80 C and stirred overnight at 80 C under nitrogen. The reaction mixture was cooled to room temperature, quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The product was purified by column chromatography or by recrystallisation.

Reference： [1]European Journal of Medicinal Chemistry,2012,vol. 47,p. 1 - 17

61
[ 1357564-27-2 ]
[ 175883-62-2 ]
[ 1357564-29-4 ]

Yield	Reaction Conditions	Operation in experiment
62%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,2-dimethoxyethane; water; at 80℃;Inert atmosphere;	General procedure: A mixture of arylbromide (1 equiv), boronic acid (1.2 equiv), cesium carbonate (4 equiv), and tetrakis(triphenylphosphine) palladium (0.02 equiv) was suspended in a DME/water (2:1) solution and the mixture was degazed. The mixture was heated to 80 C and stirred overnight at 80 C under nitrogen. The reaction mixture was cooled to room temperature, quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to dryness. The product was purified by column chromatography or by recrystallisation.

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 10719 - 10737
[2]European Journal of Medicinal Chemistry,2012,vol. 47,p. 1 - 17

62
[ 1353647-29-6 ]
[ 175883-62-2 ]
[ 1353647-43-4 ]

Reference： [1]ChemMedChem,2011,vol. 6,p. 2214 - 2224

63
[ 1335387-28-4 ]
[ 175883-62-2 ]
[ 1335386-78-1 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium 10% on activated carbon; potassium carbonate; In ethanol; water; toluene; at 80℃; for 8h;	General procedure: To a solution of Aryl iodide 8 (1equiv) in a mixture(4:2:1) of toluene, ethanol, and water was added boronic acid (1.2 equiv), Pd-C(10 wt%), K2CO3(2 equiv). The mixture was heated at 80 C for 8 h. The reaction mixture was allowed to RT and treated with CH2Cl2, The layers were separated and the aqueous layer was extracted with additional CH2Cl2, The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude product mixture was purified by column chromatography.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1976 - 1979

64
3-(4-bromo-2-fluorophenyl)-4-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-4H-1,2,4-triazole [ No CAS ]
[ 175883-62-2 ]
4-[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-[3-fluoro-3'-methyl-4'-(methyloxy)-4-biphenylyl]-4H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With potassium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 110℃; for 1h;	Example 994-[(35)-l-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-3-[3-fluoro-3'-methyl-4'- (methyloxy)-4-biphenylyl]-4H- -triazoleA mixture of 3-(4-bromo-2-fluorophenyl)-4-[(35)-l-(cyclopropylcarbonyl)-3- pyrrolidinyl]methyl}-4H-l,2,4-triazole (104 mg, 0.264 mmol), 3-methyl-4- methoxyphenylboronic acid (45 mg, 0.271 mmol), and PdCl2(dppf) (20 mg, 0.024 mmol) in 1 ,4-dioxane (2 mL) and 2 M aq. K2C03 (1.0 mL) was stirred at 110 C for 1 h. The reaction mixture was cooled to room temperature and the 1 ,4-dioxane layer was diluted with EtOAc (20 mL), washed with 1 : 1 watenbrine, dried over Na2S04, filtered, and concentrated in vacuo. The residue was purified by reverse phase HPLC (10-80%) CH3CN/water with 0.1% NH4OH) and then reverse phase HPLC (25-55% CH3CN/water with 0.1%) TFA). The desired fractions were collected, neutralized with saturated aq.I l l NaHC03, extracted with EtOAc, and the organic layer was dried over Na2S04, filtered, and concentrated in vacuo to afford the title compound (38 mg, 33%) as a solid. MS(ES)+ m/e 435.2 [M+H]+

Reference： [1]Patent: WO2012/37298,2012,A1 .Location in patent: Page/Page column 111

65
[ 3141-26-2 ]
[ 175883-62-2 ]
[ 1361306-23-1 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 2324 - 2341
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 3346 - 3366

66
[ 23062-41-1 ]
[ 175883-62-2 ]
[ 1361306-24-2 ]