[ CAS No. 5720-06-9 ]

Name: 5720-06-9|2-Methoxyphenylboronic acid|98%
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Quality Control of [ 5720-06-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 5720-06-9 ]

CAS No. :	5720-06-9	MDL No. :	MFCD00236047
Formula :	C₇H₉BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ROEQGIFOWRQYHD-UHFFFAOYSA-N
M.W :	151.96	Pubchem ID :	2733958
Synonyms :

Calculated chemistry of [ 5720-06-9 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	42.76
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) :	-6.66 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.8
Log Po/w (WLOGP) :	-0.62
Log Po/w (MLOGP) :	0.0
Log Po/w (SILICOS-IT) :	-0.76
Consensus Log Po/w :	-0.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.56
Solubility :	4.21 mg/ml ; 0.0277 mol/l
Class :	Very soluble
Log S (Ali) :	-1.42
Solubility :	5.71 mg/ml ; 0.0376 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.4
Solubility :	6.08 mg/ml ; 0.04 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.72

Safety of [ 5720-06-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P233-P260-P261-P264-P270-P271-P280-P301+P312-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P330-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 5720-06-9 ]

* 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 [ 5720-06-9 ]
Downstream synthetic route of [ 5720-06-9 ]

[ 5720-06-9 ] Synthesis Path-Upstream 1~21

1
[ 5720-06-9 ]
[ 33421-36-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 3, p. 471 - 475

2
[ 5720-06-9 ]
[ 26608-06-0 ]

Reference： [1] Patent: EP2295421, 2011, A1,
[2] Patent: EP2364980, 2011, A1,
[3] Patent: EP2468725, 2012, A1,
[4] Patent: EP2484665, 2012, A1,
[5] Patent: EP2527334, 2012, A1,
[6] Patent: EP2617712, 2013, A1,

3
[ 5720-06-9 ]
[ 50548-45-3 ]

Reference： [1] Patent: KR2016/28524, 2016, A,
[2] Patent: WO2016/198144, 2016, A1,
[3] Patent: WO2017/71791, 2017, A1,
[4] Patent: TW2017/31839, 2017, A,

4
[ 288-13-1 ]
[ 5720-06-9 ]
[ 102908-37-2 ]

Reference： [1] Helvetica Chimica Acta, 2010, vol. 93, # 5, p. 974 - 979

5
[ 5720-06-9 ]
[ 58333-75-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 14, p. 1851 - 1856

6
[ 5720-06-9 ]
[ 10130-87-7 ]

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

7
[ 5720-06-9 ]
[ 107-18-6 ]
[ 33538-83-9 ]

Reference： [1] Advanced Synthesis and Catalysis, 2012, vol. 354, # 2-3, p. 341 - 346

8
[ 5720-06-9 ]
[ 21849-89-8 ]

Reference： [1] Organic Letters, 2012, vol. 14, # 4, p. 1078 - 1081

9
[ 5720-06-9 ]
[ 89466-08-0 ]

Reference： [1] Patent: CN104788483, 2017, B,

10
[ 5720-06-9 ]
[ 766-51-8 ]
[ 89694-48-4 ]

Reference： [1] Journal of Organic Chemistry, 2004, vol. 69, # 2, p. 566 - 569
[2] Journal of Organic Chemistry, 2004, vol. 69, # 2, p. 566 - 569

11
[ 5720-06-9 ]
[ 89694-48-4 ]

Reference： [1] Tetrahedron, 1963, vol. 19, p. 821 - 826

12
[ 5720-06-9 ]
[ 578-57-4 ]
[ 21702-84-1 ]
[ 89694-45-1 ]

Reference： [1] Journal of Organic Chemistry, 2004, vol. 69, # 2, p. 566 - 569

13
[ 5720-06-9 ]
[ 89694-45-1 ]

Reference： [1] Tetrahedron, 1963, vol. 19, p. 821 - 826

14
[ 5720-06-9 ]
[ 540-37-4 ]
[ 263901-48-0 ]

Reference： [1] European Journal of Organic Chemistry, 2007, # 32, p. 5364 - 5375
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 3057 - 3061
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 6, p. 2648 - 2659

15
[ 5720-06-9 ]
[ 106-40-1 ]
[ 263901-48-0 ]

Reference： [1] ARKIVOC (Gainesville, FL, United States), 2012, vol. 2012, # 9, p. 62 - 75,14
[2] Journal of Medicinal Chemistry, 1999, vol. 42, # 15, p. 2752 - 2759

16
[ 5720-06-9 ]
[ 263901-48-0 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 6, p. 1549 - 1552

17
[ 584-12-3 ]
[ 5720-06-9 ]
[ 38527-59-2 ]

Reference： [1] Synthetic Communications, 2010, vol. 40, # 14, p. 2138 - 2146
[2] Synthesis, 2011, # 5, p. 731 - 738

18
[ 110-00-9 ]
[ 5720-06-9 ]
[ 38527-59-2 ]

Reference： [1] Journal of Organic Chemistry, 2003, vol. 68, # 2, p. 578 - 580

19
[ 5720-06-9 ]
[ 1122-91-4 ]
[ 421553-62-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium carbonate In methanol at 20℃; for 3 h; Sealed tube; Inert atmosphere	General procedure: To a round bottom flask with stir bar were added phenylboronic acid (275 mmol), 1-bromo-4-nitrobenzene (250 mmol), base (375 mmol), 1.0 molpercent catalyst 6 (9.2 mg), and solvent 4mL. The entrance was sealed with septum, and inside air was was exchanged with N2. After the mixture was stirred at room temperature for a certain period, the mixture was diluted with H2O (5ml) and Et2O (5 ml). Organic layer was concentrated in vacuo.

Reference： [1] Journal of Chemical Research, 2004, # 9, p. 593 - 595
[2] Advanced Synthesis and Catalysis, 2004, vol. 346, # 13-15, p. 1669 - 1673
[3] Synthesis, 2005, # 4, p. 537 - 542
[4] Tetrahedron Letters, 2018, vol. 59, # 31, p. 2989 - 2993
[5] ChemCatChem, 2016, vol. 8, # 4, p. 743 - 750
[6] Organometallics, 2011, vol. 30, # 8, p. 2411 - 2417
[7] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 11, p. 3429 - 3445
[8] Tetrahedron, 2017, vol. 73, # 1, p. 64 - 69

20
[ 5720-06-9 ]
[ 15164-44-0 ]
[ 421553-62-0 ]

Reference： [1] Organic Letters, 2016, vol. 18, # 2, p. 312 - 315

21
[ 5720-06-9 ]
[ 873-76-7 ]
[ 421553-62-0 ]

Reference： [1] Dalton Transactions, 2014, vol. 43, # 26, p. 10235 - 10247

[ 5720-06-9 ] Synthesis Path-Downstream 1~68

1
[ 38603-09-7 ]
[ 5720-06-9 ]
[ 83604-34-6 ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2002,vol. 390,p. 5 - 10

2
[ 5720-06-9 ]
[ 6630-33-7 ]
[ 93465-26-0 ]

Yield	Reaction Conditions	Operation in experiment
61%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In N,N-dimethyl-formamide; for 6h;Inert atmosphere; Reflux;	General procedure: To a solution of 2-bromobenzaldehyde (315 mul, 2.70 mmol) in DMF (20 ml) was added phenyl boronic acid (395 mg, 3.24 mmol), tetrakis-(triphenylphosphine)-palladium (31 mg, 0.027 mmol) and Na2CO3 (430 mg, 4.05 mmol). The result solution was stirred and refluxed for 6 h. After the reaction completed, the solution was cooled to room temperature, then partitioned between satd NaHCO3 and EtOAc, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/diethyl ether = 8:1) to afford the product (369 mg, 2.03 mmol, 75% yield).
	With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate; In water; acetonitrile; at 60℃;Inert atmosphere; Sealed vessel;	Typical preparative procedures were performed on 10.0 mmol scale using a Mettler-Toledo FlexiWeigh 30 automated solid handling unit to pre-weigh the aryl halide (10.0 mmol, 1.0 equiv), aryl boronic acid (12.0 mmol, 1.2 equiv) and Pd-118 (65.2 mg, 0.1 mmol, 1.0 mol %). Acetonitrile (10.0 mL) was added, followed by K2CO3 added as a stock aqueous solution (10.0 mL water containing 2.07 g, 15.0 mmol, 1.5 equiv). NB. No internal standard was added for preparative reactions. Reaction mixtures were sealed under a N2 atmosphere and heated to 60 C with magnetic stirring. HPLC analysis showed that reactions using aryl bromides were complete within 1 h but that aryl chlorides typically required 24 h.After reaction mixtures had cooled to room temperature, stirring was stopped and the phases were allowed to separate. The lower aqueous phase was removed and discarded (cutting away any interfacial catalyst residues if present) and the acetonitrile phase concentrated to dryness to give typically a light to dark brown solid or dark-coloured gum. Solids were triturated with methanol (20 mL) for 1-2 h, then isolated by filtration, washed once or twice with methanol (4 mL each wash) and dried under vacuum. Oils were purified by flash silica gel chromatography as noted below. All isolated compounds gave 1H NMR data in agreement with published values. Literature data is given for mp values for comparison.

Reference： [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 1643 - 1646
[2]Journal of the American Chemical Society,2004,vol. 126,p. 13320 - 13325
[3]Journal of Organic Chemistry,2002,vol. 67,p. 6264 - 6267
[4]Advanced Synthesis and Catalysis,2004,vol. 346,p. 1669 - 1673
[5]Tetrahedron,2010,vol. 66,p. 2111 - 2118
[6]Journal of the American Chemical Society,2019,vol. 141,p. 8825 - 8833
[7]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2568 - 2576
[8]Journal of Medicinal Chemistry,2013,vol. 56,p. 1323 - 1340
[9]Tetrahedron,2012,vol. 68,p. 6010 - 6017
[10]RSC Advances,2015,vol. 5,p. 8801 - 8805

3
[ 5720-06-9 ]
[ 89-98-5 ]
[ 93465-26-0 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 4685 - 4696

4
[ 29976-20-3 ]
[ 5720-06-9 ]
C₂₁H₂₁NO₂ [ No CAS ]

Reference： [1]Synthesis,2006,p. 2855 - 2864

5
[ 101066-87-9 ]
[ 5720-06-9 ]
C₁₅H₁₀F₃NO [ No CAS ]

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

6
[ 5720-06-9 ]
2-halido-5-methylthiophene [ No CAS ]
[ 93465-26-0 ]

Reference： [1]Chemical Communications,2007,p. 754 - 756

7
[ 5720-06-9 ]
[ 58333-75-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 1851 - 1856

8
[ 328918-33-8 ]
[ 5720-06-9 ]
[ 247940-06-3 ]
[ 328918-90-7 ]
[ 328919-10-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride;palladium diacetate; In tetrahydrofuran;	A. 2-(4-{2-[2-(2'-Methoxy-biphenyl-4-yl)-5-methyloxazol-4-yl]-ethoxy}-phenoxy)-2-methylpropionic acid ethyl ester A solution of 2-(4-{2-[2-(4-bromophenyl)-5-methyloxazol-4-yl]ethoxy}phenoxy)-2-methylpropionic acid ethyl ester (300 mg, 0.614 mmol) (see Ex. 2, part B), o-methoxyphenylboronic acid (140 mg, 0.921 mmol), potassium fluoride (88.6 mg, 1.84 mmol), palladium acetate (1.3 mg, 0.14 mumol), and 2-(dicyclohexylphosphino)biphenyl (4.3 mg, 12.3 mumol) were combined under N2, to which anhydrous THF (1.23 mL) was added. The yellow mixture was heated at reflux for 12 h. After cooling to room temperature, the mixture was partitioned between Et2O (20 mL) and 1M NaOH (10 mL). The layers were separated, and the aqueous phase was back-extracted with Et2O (10 mL). Combined organic phases were dried over Na2SO4, and concentrated. The product was purified by silica gel chromatography (25 g SiO2, 1:4 ethyl acetate:hexanes) to yield 100.5 mg (32%) as an oil. Rf=0.38 in 1:4 ethyl acetate:hexanes; 1H NMR (400 MHz, CDCl3) delta7.97 (d, J=8.0 Hz, 2H), 7.57 (d, J=8.0 Hz, 2H), 7.33-7.29 (m, 2H), 7.01 (t, J=7.2 Hz, 1H), 6.97 (d, J=7.6 Hz, 1H), 6.80-6.74 (m, 4H), 4.20 (q, J=7.2 Hz, 2H), 4.17 (t, J=6.8 Hz, 2H), 3.80 (s, 3H), 2.94 (t, J=6.8 Hz, 2H), 2.34 (s, 3H), 1.50 (s, 6H), 1.24 (t, J=7.2 Hz, 3H); MS (EI) 538.2 (M+Na)+, 516.2 (M+H)+.

Reference： [1]Patent: US6417212,2002,B1

9
potassium phosphate [ No CAS ]
[ 2142-68-9 ]
[ 5720-06-9 ]
[ 224311-51-7 ]
2-methoxy-2'-acetylbiphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
201 mg (89%)	palladium diacetate; In toluene;	EXAMPLE 42 Synthesis of 2-methoxy-2'-acetylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), 2-methoxyphenylboronic acid (228 mg, 1.5 mmol), and potassium phosphate (425 mg, 2.0 mmol). The tube was evacuated and backfilled with argon, and toluene (3 mL) and 2'-chloroacetophenone (0.13 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was heated to 65° C. with stirring until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 201 mg (89percent) of the title compound.
201 mg (89%)	palladium diacetate; In toluene;	Example 42 Synthesis of 2-methoxy-2'-acetylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), 2-methoxyphenylboronic acid (228 mg, 1.5 mmol), and potassium phosphate (425 mg, 2.0 mmol). The tube was evacuated and backfilled with argon, and toluene (3 mL) and 2'-chloroacetophenone (0.13 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was heated to 65° C. with stirring until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL) and poured into a separatory funnel. The mixture was washed with water (20 mL), and the aqueous layer was extracted with ether (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 201 mg (89percent) of the title compound.

Reference： [1]Patent: US6307087,2001,B1
[2]Patent: US2004/171833,2004,A1

10
[ 106-43-4 ]
[ 5720-06-9 ]
[ 224311-51-7 ]
[ 92495-53-9 ]

Yield	Reaction Conditions	Operation in experiment
188 mg (95%)	With potassium fluoride;palladium diacetate; In tetrahydrofuran;	EXAMPLE 41 Synthesis of 2-methoxy-4'-methylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), 2-methoxyphenylboronic acid (228 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 4-chlorotoluene (0.144 ml, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at 65° C. until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 188 mg (95percent) of the title compound.
188 mg (95%)	With potassium fluoride;palladium diacetate; In tetrahydrofuran;	Example 41 Synthesis of 2-methoxy-4'-methylbiphenyl An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol percent), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol percent), 2-methoxyphenylboronic acid (228 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) and 4-chlorotoluene (0.144 mL, 1.0 mmol) were added through a rubber septum. The tube was sealed with a teflon screwcap, and the reaction mixture was stirred at 65° C. until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ether (30 mL), filtered through celite, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 188 mg (95percent) of the title compound.

Reference： [1]Patent: US6307087,2001,B1
[2]Patent: US2004/171833,2004,A1

11
[ 1532-71-4 ]
[ 5720-06-9 ]
[ 134948-96-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 50℃; for 12h;	Stage A: 1 -(2-methoxyphenyl)isoquinoline.A solution of <strong>[1532-71-4]1-<strong>[1532-71-4]bromoisoquinoline</strong></strong> (2.06 g, 10 mmol), prepared as described in EuropeanJournal of Organic Chemistry 2002, 4181-4184, 2-methoxyphenylboronic acid (2.79 g, 10 mmol), Pd(PPh3)4 (5percentmol), K2CO3 (5g) in DMF/water (3/1) is stirred at 500C for 12 hours.The reaction mixture is then pored on water (150 mL). The aqueous phase is extracted with EPO <DP n="84"/>ethyl acetate (3xl00mL). The combined organic layers are washed with water (3x200mL).The organic phase is dried over magnesium sulfate and evaporated under vacuum to afford the title compound.

Reference： [1]Patent: WO2006/103120,2006,A2 .Location in patent: Page/Page column 82-83

12
[ 19393-92-1 ]
[ 5720-06-9 ]
[ 852112-02-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 90℃;	Intermediate 85 2',6'-Dichloro-2-methoxy-biphenyl: To a solution of 2,6-dichlorobenzene bromide (22.9 g, 87 mmol) and sodium hydroxide (10.1 g, 0.22 mol) in DME-water (2:1) was added 2-methoxy benzene boronic acid (20 g, 0.13 mol) at 90° C., followed by tetrakis(triphenylphosphine)-palladium (0) (5.8 g, 4.3 mmol). The reaction mixture was heated at 90° C. overnight and cooled to room temperature. The mixture was extracted with methylene chloride and washed with water. The organic solvent was removed under vacuum. Chromatography with 5percent ethyl acetate in hexanes afforded 23.57 g (93percent) of the title compound as a colorless oil. MS EI m/e 252 M+
76%	With sodium hydroxide;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 50 - 80℃; for 18.8333h;	Example 1 Preparation of 2,6-dichloro-2'-methoxybiphenyl (110):(108) (109) (110)[0097] To a 100-L reactor were charged 2-methoxybenzeneboronic acid (109) (3.51 kg, 23.1 mol, 1.37eq) and a solution of 2-bromo-l, 3-dichlorobenzene (108) in dimethoxyethane (DME, 7.64 kg, 50 w/wpercent, 16.9 mol). To this mixture was added dimethoxyethane (DME, 29 kg). The reaction contents were stirred to provide a solution, and the solution was then heated to 50 0C. To this solution was added a 4.4 M aqueous solution of sodium hydroxide (3.55 kg of NaOH in 19.0 kg of water, 5.0 eq) over a 20 minute period,Page 38 of 58Attorney Docket No. 2004658-1130 (AM102450) 426261 Iv2 EPO <DP n="40"/>maintaining a temperature of 50 + 5 0C. The reaction was then heated to 70 0C over 15 minutes, followed by addition of Pd(PPtLs)4 (0.41 kg, 0.35 mol, 2 molpercent) in one portion. The mixture was gradually heated to reflux ( to 80 0C) over a 15 minute period, and was then stirred at 80 + 20C for 18 hours. At that time, the reaction was cooled to room temperature (22 - 25 0C), the DME/water layers were separated, and the organic layer was concentrated under reduced pressure to obtain a brown oil. To this brown oil was added tert-butyl methyl ether (TBME) (15.0 kg) and water (12.0 kg). The mixture was heated to 33 + 2 0C, and recirculated with a R53-SP Zeta filter cartridge for 4 h (charcoalization). The amber-colored TBME organic layer was separated. The organic layer was washed with water (2 X 12.0 kg). TBME was removed by atmospheric distillation to obtain 16 +/- 2 L. IPA (2 X 8.0 kg) was then added to replace TBME and the IPA solution (8 +/- 2 L) was cooled to 0 to 10 0C to induce crystallization. The crystals were filtered, washed with IPA (2 x 5.0 kg), and dried at 45 0C for 20 h to obtain 3.4 kg (76percent) of compound (110). 1H NMR (300 MHz, DMSO-J6) delta 7.54 (dd, J= 0.9, 7.8 Hz, 2H), 7.46-7.37 (m, 2H), 7.15-7.02 (m, 3H).
49%	With potassium carbonate;trans-dichlorobis(tri-o-tolylphenylphosphane)palladium(II); In 1,4-dioxane; water; at 100℃; for 36h;	A mixture of l-bromo-2,6-dichlorobenzene (5.0 g, 0.022 mol), 2- methoxyphenylboronic acid (5.045 g, 0.033 mol) and potassium carbonate (7.65 g, 0.055 mol) in dioxane (130 mL) and water (13 mL) was purged with nitrogen for 20 minutes. rroeroe-dichlorobis(tri-o-tolylphosphine)palladium (II) (0.87 g, 0.0011 mol) was added and the reaction mixture heated to 100 0C for 36 hours. The cooled reaction mixture was then filtered through celite washing the filter cake with ethyl acetate. The combined organic filtrates were diluted to 500 mL by the addition of ethyl acetate, then washed with 2.0 M aqueous sodium hydroxide (2 x 350 mL), water (350 mL) and saturated brine (350 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford a yellow oil. Purification by flash chromatography using a solvent gradient of 0.5 to 2percent ethyl acetate in hexane gave 2.74 g (49percent) of 2',6'-dichloro-lJ'-biphenyl-2-yl methyl ether as a white solid. MS (EI) mlz 252 (M+).

Reference： [1]Patent: US2006/241172,2006,A1 .Location in patent: Page/Page column 57
[2]Patent: WO2008/52088,2008,A1 .Location in patent: Page/Page column 38-39
[3]Chemistry - A European Journal,2010,vol. 16,p. 4075 - 4081
[4]Patent: WO2006/116165,2006,A1 .Location in patent: Page/Page column 81

13
[ 905590-33-2 ]
aqueous potassium carbonate [ No CAS ]
[ 5720-06-9 ]
[ 247940-06-3 ]
4-(3,4-diethoxyphenyl)-N-[4-(2-methoxyphenyl)-6-phenylpyridin-2-yl]-4-oxobutanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	tris-(dibenzylideneacetone)dipalladium(0);	Example 146 4-(3,4-diethoxyphenyl)-N-[4-(2-methoxyphenyl)-6-phenylpyridin-2-yl]-4-oxobutanamide Using N-(4-chloro-6-phenylpyridin-2-yl)-4-(3,4-diethoxyphenyl)-4-oxobutanamide obtained in Example 43-(3) (22.6 mg), tris(dibenzylideneacetone)dipalladium (1.1 mg), biphenyl-2-yl(dicyclohexyl)phosphine (1.8 mg), 1N aqueous potassium carbonate solution (0.1 mL) and (2-methoxyphenyl)boronic acid (19.0 mg) as starting materials and in the same manner as in Example 119, 4-(3,4-diethoxyphenyl)-N-[4-(2-methoxyphenyl)-6-phenylpyridin-2-yl]-4-oxobutanamide (7.5 mg) was obtained. HPLC (220 nm) purity 95% (retention time 2.05 min) MS (ESI+, m/e) 525 (M+H)

Reference： [1]Patent: EP1845081,2007,A1

14
[ 905590-58-1 ]
aqueous potassium carbonate [ No CAS ]
[ 5720-06-9 ]
[ 247940-06-3 ]
4-(2,3-dihydro-1-benzofuran-5-yl)-N-[4-(2-methoxyphenyl)-6-phenylpyridin-2-yl]-4-oxobutanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	tris-(dibenzylideneacetone)dipalladium(0);	Example 178 4-(2,3-dihydro-1-benzofuran-5-yl)-N-[4-(2-methoxyphenyl)-6-phenylpyridin-2-yl]-4-oxobutanamide Using N-(4-chloro-6-phenylpyridin-2-yl)-4-(2,3-dihydro-1-benzofuran-5-yl)-4-oxobutanamide obtained in Example 114-(1) (20.3 mg), tris(dibenzylideneacetone)dipalladium (1.1 mg), biphenyl-2-yl(dicyclohexyl)phosphine (1.8 mg), 1N aqueous potassium carbonate solution (0.1 mL) and (2-methoxyphenyl)boronic acid (19.0 mg) as starting materials and in the same manner as in Example 119, 4-(2,3-dihydro-1-benzofuran-5-yl)-N-[4-(2-methoxyphenyl)-6-phenylpyridin-2-yl]-4-oxobutanamide (14.0 mg) was obtained. HPLC (220 nm) purity 96% (retention time 1.99 min) MS (ESI+, m/e) 479 (M+H)

Reference： [1]Patent: EP1845081,2007,A1

15
[ 73096-42-1 ]
[ 5720-06-9 ]
[ 1029083-89-3 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 2743 - 2747

16
[ 5720-06-9 ]
[ 133852-23-0 ]
[ 1159059-91-2 ]

Reference： [1]Synlett,2009,p. 720 - 723

17
[ 2516-40-7 ]
[ 5720-06-9 ]
[ 6269-47-2 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1450 - 1458

18
[ 5720-06-9 ]
[ 2941-58-4 ]
[ 1122521-71-4 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1450 - 1458

19
[ 1193-21-1 ]
[ 46004-37-9 ]
[ 5720-06-9 ]
2-chloro-4-[6-(2-methoxy-phenyl)-pyrimidin-4-ylamino]-benzoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		4, 6-Dichloropyrimidine (0. 72mmol), 2-METHOXYPHENYLBORONIC acid (0. 66 mmol), sodium carbonate (1. 97 mmol), and Pd (PPh3) 2CI2 (3 mol%) were suspended in a mixture of DME/ETOH/WATER (2. 5 ML/0. 38 ML/0. 38 ML). The mixture was heated in a Personal Chemistry Optimizer microwave system at 130C for 900 s. 'PrOH (5 ml) and the corresponding aniline derivative (0. 66 MMOL) were added, and the mixture was treated with conc. HCI under stirring to reach a pH value of 1- 2. The mixture was then heated in the microwave at 150C for 900 s. The solvent was evaporated under reduced pressure and the residue suspended in H20 (10 mL). With sat. NAHC03 solution the mixture was set to pH = 6-7 and extracted with EtOAc (3x 20 ML). The combined organics were washed with brine and dried over NA2SO4. After evaporation of the solvent the residue was taken up in DMSO and purified via prep.-HPLC (XTerra Prep. MS C18 5 um, 19 x 150 mm, gradient from water to MeCN over 13 min). In the case of products with an acid group in the anilino part, the corresponding methyl esters were prepared via treatment with TMSCHN2 (2-4 eq.) in DCM/MEOH (2 mL/1 mL) at room temperature.

Reference： [1]Patent: WO2005/26129,2005,A1 .Location in patent: Page/Page column 97

20
[ 16732-64-2 ]
[ 5720-06-9 ]
[ 1182349-25-2 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5093 - 5107

21
[ 1780-40-1 ]
[ 5720-06-9 ]
[ 1239984-17-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1429 - 1433

22
[ 1780-40-1 ]
[ 5720-06-9 ]
[ 1239984-29-2 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1429 - 1433

23
[ 1780-40-1 ]
[ 5720-06-9 ]
[ 1239984-51-0 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium phosphate; palladium diacetate; triphenylphosphine; In water; acetonitrile; at 20 - 60℃; for 2h;	(1) A mixture of <strong>[1780-40-1]perchloropyrimidine</strong> (15 g, 65.4 mmol), (2-methoxyphenyl)boronic acid (10.14 g, 65.4 mmol), triphenylphosphine (1.716 g, 6.54 mmol), palladium acetate (0.734 g, 3.27 mmol) and potassium phosphate, H2O (45.2 g, 196 mmol) in acetonitrile (300 ml)/water (90 ml) was degassed at room temperature. The mixture was stirred at room temperature for 1 hr. before heated at 60 C for 1 hr. Upon completion of the reaction, the reaction was diluted with ethyl acetate, washed with sodium chloride saturated solution, filtered and evaporated. The crude material was purified by silica gel column chromatography using heptanes/AcOEt: 93/7 to 8/2 as eluent to afford a white solid (10.6 g, 56% yield).

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1429 - 1433
[2]Patent: EP2910555,2015,A1 .Location in patent: Paragraph 0074

24
[ 288-13-1 ]
[ 5720-06-9 ]
[ 102908-37-2 ]

Reference： [1]Helvetica Chimica Acta,2010,vol. 93,p. 974 - 979

25
[ 28342-75-8 ]
[ 5720-06-9 ]
C₂₀H₁₆F₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; toluene; for 8h;Reflux; Inert atmosphere;	1,3-dibromo-4, 6-difluorobenzene (50.0 g, 183. 9 mmol), 2-methoxyphenylboronic acid (67.1 g, 441. mmol), and a 2 M aqueous solution of Na2CO3 (368 mL, 736 mmol), DME (370 mL), toluene (370 mL), and Pd[PPh3]4 (21.3g, 18.4 mmol) were loaded into a three-necked flask, and the mixture was refluxed under an Ar atmosphere for 8 hours. After the completion of the reaction, the resultant was cooled to room temperature. The resultant sample was transferred to a separating funnel, and water (500 mL) was charged into the funnel. Then, the mixture was extracted with CH2Cl2. The extract was dried with MgSO4, and was then filtrated and concentrated. The resultant sample was purified by silica gel column chromatography, whereby a white solid was obtained in an amount of 40.2 g in 67percent yield. FD-MS C20H16F2O2: theoretical value 326, observed value 326
67%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; toluene; for 8h;Reflux; Inert atmosphere;	<strong>[28342-75-8]1,3-dibromo-4,6-difluorobenzene</strong> (50.0 g, 183-9mmol), 2-methoxyphenylboronic acid (67.1 g, 441.4 mmol), a 2 M aqueous solution of Na2CO3 (368 mL, 736 mmol), DME (370 mL), toluene (370 mL), and Pd[PPh3]4 (21 g, 18.0 mmol) were loaded into a three-necked flask, and the mixture was refluxed under an Ar atmosphere for 8 hours. After the completion of the reaction, the resultant was cooled to room temperature. The resultant sample was transferred to a separating funnel, and water (500 mL) was charged into the funnel. Then, the mixture was extracted with CH2Cl2. The extract was dried with MgSO4 and was then filtered and concentrated. The resultant sample was purified by silica gel column chromatography, whereby a white solid was obtained in an amount of 40.2 g in 67percent yield-FD-MS analysis C20H16F2O2: theoretical value 326, observed value 326

Reference： [1]Patent: EP2301921,2011,A1 .Location in patent: Page/Page column 136
[2]Patent: EP2301926,2011,A1 .Location in patent: Page/Page column 113

26
[ 5720-06-9 ]
[ 1439-09-4 ]
[ 1353577-92-0 ]

Reference： [1]Synthesis,2011,p. 3496 - 3506

27
[ 5720-06-9 ]
[ 107-18-6 ]
[ 33538-83-9 ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 341 - 346

28
[ 5720-06-9 ]
[ 120068-79-3 ]
5-amino-1-(2,6-dichloro-4-(trifluoromethyl)phenyl)-4-(2-methoxyphenyl)-1H-pyrazole-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With bis-triphenylphosphine-palladium(II) chloride; N-iodo-succinimide; sodium hydrogencarbonate; In ethanol; water; at 80℃; for 18h;Inert atmosphere;	General procedure: Phenylpyrazole (0.2 mmol), arylboronic acid (0.4 mmol), NIS (0.2 mmol), [Pd] (10 mol%), NaHCO3 (0.4 mmol) and C2H5OH:H2O (3:1, 10 mL), were added to a Schlenk tube. Then the tube was charged with N2 and the reaction mixture was stirred at 80 C for 18 h. After the completion of the reaction, as monitored by TLC, the mixture was cooled and filtrated. The filtrate was extracted with ethyl acetate and washed with brine. Then the combined organic extracts were dried over Na2SO4, concentrated under vacuum and the resulting residue was purified by silica gel column chromatography to afford the desired products.

Reference： [1]Journal of Fluorine Chemistry,2012,vol. 137,p. 44 - 49

29
[ 109179-31-9 ]
[ 5720-06-9 ]
[ 94235-91-3 ]

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

30
[ 337958-60-8 ]
[ 5720-06-9 ]
[ 1400679-64-2 ]

Reference： [1]Synthesis,2012,vol. 44,p. 2255 - 2263

31
[ 337958-60-8 ]
[ 5720-06-9 ]
[ 1400679-74-4 ]

Reference： [1]Synthesis,2012,vol. 44,p. 2255 - 2263

32
[ 5720-06-9 ]
[ 65896-11-9 ]
[ 1338379-58-0 ]

Yield	Reaction Conditions	Operation in experiment
62%	With palladium diacetate; 2-dicyclohexylphosphino-2',6'-dimethylbiphenyl; In toluene; at 100℃; for 3h;	A well-dried 200 mL three-neck eggplant flask(Condenser, with three-way cock, with magnetic stir bar)2-Methoxyphenylboronic acid3.19 g (21 mmol), 2.80 g of <strong>[65896-11-9]2-bromo-6-fluoroaniline</strong> (manufactured by Tokyo Chemical Industry Co., Ltd.)(20 mmol), 0.022 g of palladium acetate(0.1 mmol) 2-Dicyclohexylphosphino-2 ', 6'-dimethylbiphenyl0.082 g (0.2 mmol),13.8 g (60 mmol) of potassium phosphate monohydrate was added,The mixture was suspended in 40 mL of toluene and reacted at 100 C. for 3 hours.After adding 100 mL of water to this reaction solution and extracting with toluene,The organic layer is dried over MgSO4The solvent was distilled off under reduced pressure to obtain a crude product.Crude product is silica gel column chromatograph(Eluent: hexane / ethyl acetate = 93/7)Compound 4 by purifying with2.71 g (62%, light yellow liquid) was obtained.

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 12438 - 12441
[2]Patent: JP5769444,2015,B2 .Location in patent: Paragraph 0167-0169

33
[ 38603-09-7 ]
[ 5720-06-9 ]
[ 14079-42-6 ]

Reference： [1]Journal of Physical Organic Chemistry,2012,vol. 25,p. 878 - 882

34
[ 640280-28-0 ]
[ 5720-06-9 ]
C₁₄H₁₀BrF₃O [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 16955 - 16958,4
[2]Journal of the American Chemical Society,2014,vol. 136,p. 8887 - 8890

35
[ 5720-06-9 ]
[ 29681-42-3 ]
[ 1292307-24-4 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 50℃; for 5h;Inert atmosphere;	Step 1 : A reaction mixture of 2-methoxyphenylboronic acid 120 (600 mg, 4 mmol), Cs2C03 (2.6 g, 8 mmol), Pd(PPh3)4 (200 mg, 0.2 mmol) and methyl 4- bromopicolinate 121 (864 mg, 4 mmol) in DMF ( 4 mL), was degassed and heated to 50 C under Argon for 5 hr. The mixture was filtered through Celite and was concentrated. The crude residue was purified by silica gel chromatography (gradient, 10% to 50% EtOAc/hexanes) to give methyl 4-(2- methoxyphenyl)picolinate 122. LC/MS RT (5 min method) = 1.703 min. Mass observed: 244.1 (M+H).

Reference： [1]Patent: WO2011/46771,2011,A1 .Location in patent: Page/Page column 210

36
[ 1435-53-6 ]
[ 5720-06-9 ]
[ 1424360-05-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 90℃; for 8h;Inert atmosphere;	General procedure: 8.3 1,3-Di(2'-methoxyphenyl)-4-fluorobenzene (11c): Starting with 10 (100 mg, 0.39 mmol), Cs2CO3 (253 mg, 0.78 mmol), Pd(PPh3)4 (3 mol%), 2-methoxyphenylboronic acid (94 mg, 78 mmol) and 1,4-dioxane (4 mL), 11c was isolated as a colorless solid (73 mg, 60%). Mp 99-100 C. 1H NMR (300 MHz, CDCl3): delta = 3.75, 3.75 (s, 3H, OCH3), 6.89-6.98 (m, 4H, ArH), 7.04-7.11 (m, 1H, ArH), 7.17-7.25 (m, 3H, ArH), 7.39-7.48 (m, 2H, ArH). 13C NMR (75 MHz, CDCl3): delta = 55.6, 55.7 (OCH3), 111.1 (CH), 111.2 (CH), 114.9 (d, J = 22.5 Hz, CH), 120.5 (CH), 120.9 (CH), 128.7 (2C), 125.7 (d, J = 15.8 Hz, C), 130.1 (d, J = 8.3 Hz, CH), 130.9 (2CH), 131.5 (2CH), 133.0 (d, J = 8.3 Hz, CH), 134.1 (d, J = 3.8 Hz, C), 157.1, 157.6 (C), 159.1 (d, J = 244.0 Hz, CF). 19F NMR (282 MHz, CDCl3): delta = -116.36 (CF). IR (ATR, cm-1): , 2959 (m), 2924 (m), 2852 (m), 2836 (m), 1577 (m), 1494 (s), 1455 (s), 1434 (m), 1390 (m), 1256 (m), 1228 (m), 1109 (m), 1022 (s), 825 (m), 792 (m), 825 (s), 792 (s), 748 (s), 625 (m), 597 (m), 544 (m). GC-MS (EI, 70 eV); m/z (%) = 308 (100) [M]+, 278 (13), 260 (6), 233 (10), 110 (3). HRMS (EI) calcd. for C20H17O2F[M]+: 308.12071; found 308.12018.

Reference： [1]Journal of Fluorine Chemistry,2013,vol. 146,p. 19 - 36

37
[ 5720-06-9 ]
[ 10130-87-7 ]

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

38
[ 5720-06-9 ]
[ 290368-00-2 ]
3-(2-methoxyphenyl)-1H-indazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 120℃; for 1h;Microwave irradiation;	General procedure: <strong>[290368-00-2]ter<strong>[290368-00-2]t-butyl 3-iodo-1H-indazole-1-carboxylate</strong></strong> (S2, 100 mg, 0.29 mmol) was placed in a microwave vial and dissolved in 1,4-dioxane (11.5 mL). 3-Methoxyphenylboronic acid (88 mg, 0.58 mmol, 2.0 equiv) and tetrakis(triphenylphosphine)palladium (20 mg, 0.017 mmol, 0.06 equiv) were added, and the resulting mixture was sparged thoroughly with nitrogen. An aqueous solution of sodium carbonate (2.0 M, 0.65 mL, 1.3 mmol, 4.5 equiv) was then added. The biphasic mixture was microwaved for 1 hour at a reaction temperature of 120 C. After cooling to room temperature, the reaction was diluted with ethyl acetate (2 mL), and then filtered through a celite pad with additional ethyl acetate. The filtrate was concentrated under reduced pressure to give an oil. The crude material was purified by column chromatography over silica gel (hexanes/ethyl acetate: 100/0 to 30/70) to give the title compound as an oil (58.0 mg, 89%).

Reference： [1]Beilstein Journal of Organic Chemistry,2013,vol. 9,p. 1501 - 1507

39
[ 89167-19-1 ]
[ 5720-06-9 ]
3-bromo-4-(2-methoxyphenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; for 2h;Inert atmosphere;	3-Bromo-4-iodopyridine (2.2 g, 7.8 mmol), 2-Methoxyphenylboronic acid (1.3 g, 8.6 mmol), sodium carbonate (1.7 g, 15.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.22 g, 0.19 mmol) were charged and vessel evacuated and purged with nitrogen. Added nitrogen degassed 3:1 solution of dioxane and water (15 ml) and reaction heated to 100C for 2 hrs. Reaction was partitioned between EtOAc and water. The organics were washed with brine, dried and concentrated. The crude product was purified by flash column using a gradient of 100% Hexanes to 1:1 Hexanes and EtOAc to isolate the product as a glassy solid. LC-MS m z: 264 [M+l]

Reference： [1]Patent: WO2013/62887,2013,A1 .Location in patent: Page/Page column 64

40
[ 20511-15-3 ]
[ 5720-06-9 ]
3-amino-4-(2-methoxyphenyl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17 g	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium carbonate; In 1,4-dioxane; for 36h;Reflux;	To apre-mixed solution of tris(dibenzylideneacetone)dipalladium (5.83mmol, 5.34g) and 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (11.67mmol, 4.79g) in dioxane (120mL) was added 4-chloropyridin-3 -amine (117mmol, 15g), 2M Na2C03 (351mmol) and 2- methoxyboronic acid (152mmol, 23.05g). The mixture was diluted with an additional lOOmL of dioxane and refluxed for 36 h. The reaction was complete as judged by LCMS and TLC. The solution was allowed to cool to RT and diluted with EtOAc (lOOmL). The organic layer was washed with water and brine and dried with MgS04. The solution was filtered and concentrated under vacuum. The crude product was purified by chromatography on silica gel, eluting with EtOAc / Hexane to afford the title compound (17g). LC/MS: m/e 201.2 (M+H). 1H NMR (500 MHz, CDC13): delta 8.17 (IH, s), 8.08 (IH, d), 7.43 (1, t), 7.27 (IH, dd), 7.09 (IH, t), 7.05 (IH, d), 7.04 (IH, s), 3.85 (3H, s), 3.78 (2H, s).

Reference： [1]Patent: WO2013/62887,2013,A1 .Location in patent: Page/Page column 45-46

41
[ 15813-09-9 ]
[ 5720-06-9 ]
4-iodo-5-(2-methoxyphenyl)-1H-imidazole [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 3231 - 3243

42
[ 15813-09-9 ]
[ 5720-06-9 ]
[ 109811-95-2 ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 3231 - 3243

43
[ 5720-06-9 ]
[ 21419-48-7 ]
6-(2-methoxyphenyl)quinazolin-4-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 3484 - 3493

44
[ 5720-06-9 ]
[ 99-90-1 ]
[ 20712-12-3 ]
[ 1513888-94-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 3114 - 3122

45
[ 1337532-51-0 ]
[ 5720-06-9 ]
5-(2-methoxyphenyl)-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]

Reference： [1]MedChemComm,2014,vol. 5,p. 1500 - 1506

46
[ 5720-06-9 ]
[ 189628-37-3 ]
C₁₄H₁₁ClO₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 8053 - 8066

47
[ 5720-06-9 ]
[ 62129-39-9 ]
(S)-2-t-butoxycarbonylamino-3-(2'-methoxy-biphenyl-4-yl)-propionic acid [ No CAS ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 5410 - 5413

48
[ 4765-77-9 ]
[ 5720-06-9 ]
6-(2-methoxyphenyl)pyrimidin-4(3H)-one [ No CAS ]

Reference： [1]ACS Chemical Neuroscience,2019,vol. 10,p. 1099 - 1114
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 388 - 409

49
[ 5720-06-9 ]
[ 90905-31-0 ]
2-(2-methoxyphenyl)pyrimidine-5-carbaldehyde [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 7426 - 7432

50
[ 5720-06-9 ]
[ 450412-29-0 ]
6-bromo-2-fluoro-2’-methoxy-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With bis-triphenylphosphine-palladium(II) chloride; borax; hydrazine hydrate; In tetrahydrofuran; water; at 70℃; for 48h;Inert atmosphere;	200 g(664 mmol) <strong>[450412-29-0]1-bromo-3-fluoro-2-iodobenzene</strong>, 101 g (664 mmol) of 2-methoxy-phenylboronicacid and sodium tetraborate 137.5 g (997 mmol) were dissolved in 1000 ml THFand 600 ml water, and degassed. 9.3 g (13.3 mmol) of bis (triphenylphosphine)palladium (II) chloride and 1 g (20 mmol) hydrazinium hydroxide was added. The reaction mixture was stirred at 70C for 48 h under a protective gas atmosphere, cooled, washed several times with water, dried and evaporated. The reaction mixture was purified by silica gel column chromatography using toluene/heptane (2:1). Yield 155 g (553 mmol), 83%.
83%	With bis-triphenylphosphine-palladium(II) chloride; sodium tetraborate; hydrazine hydrate; In tetrahydrofuran; water; at 70℃; for 48h;Inert atmosphere;	200 g (664 mmol) of <strong>[450412-29-0]1-bromo-3-fluoro-2-iodobenzene</strong>, 101 g (664 mmol) of2-methoxyphenylboronic acid and 137.5 g (997 mmol) of sodium tetraborate are dissolved in 1000 ml of THF and 600 ml of water and degassed. 9.3g (13.3 mmol) of bis(triphenylphosphine)palladium(Il) chloride and 1 g (20 mmol) of hydrazinium hydroxide are added. The reaction mixture is subsequently stirred at 70C for 48 h under a protective-gas atmosphere. The cooled solution is diluted with toluene, washed a number of times with water, dried and evaporated. The product is purified by column chromatography on silica gel with toluene/heptane (1:2). Yield: 155 g (553 mmol), 83% of theory.
83%	With bis-triphenylphosphine-palladium(II) chloride; borax; hydrazine hydrate; In tetrahydrofuran; water; at 70℃; for 48h;Inert atmosphere;	200 g (664 mmol) of <strong>[450412-29-0]1-bromo-3-fluoro-2-iodo-benzene</strong>, 101 g (664 mmol) of 2-methoxyphenyl-boronic acid and 137.5 g (997 mmol) of sodium (0136) tetraborate are dissolved in 1000 mL of THF and 600 ml of water and degassed. Afterwards, 9.3 g (13.3 mmol) of bis (triphenylphosphine) palladium (II) chloride and 1 g (20 mmol) of hydrazinium hydroxide are added to the reaction mixture, which is then stirred at 70 C for 48 h under inert gas atmosphere. The cooled solution is completed with toluene, washed several times with water, dried and concentrated. The product washed via column chromatography on silica gel with toluene/heptane: (1 :2). (0137) Yield: 155 g (553 mmol), 83% of theory.

83%	With bis-triphenylphosphine-palladium(II) chloride; borax; hydrazine hydrate; In tetrahydrofuran; water; at 70℃; for 48h;	200 g (664 mmol) of <strong>[450412-29-0]1-bromo-3-fluoro-2-iodobenzene</strong>,101 g (664 mmol) of 2-methoxyphenylboronic acid and 137.5 g (997 mmol) of sodium tetraborate were dissolved in 1000 ml of THF and 600 ml of water and degassed.9.3 g (13.3 mmol) of bis (triphenylphosphine) palladium (II) dichloride and 1 g (20 mmol) of hydrazine hydroxide were added.The reaction mixture was stirred at 70 C for 48 hours under a protective atmosphere.Toluene was added to the cooled solution,Wash repeatedly with water, dry and concentrate.The product was purified by silica gel column chromatography with toluene / heptane (1: 2). Yield: 155 g (553 mmol),Theoretical yield 83%.
83%	With borax; trans-bis(triphenylphosphine)palladium dichloride; hydrazine hydrate; In tetrahydrofuran; water; at 70℃; for 48h;Inert atmosphere;	200 g (664 mmol) of 1-bromo-3-fluoro-2-iodoben- zene, 101 g (664 mmol) of 2-methoxyphenylboronic acid and 137.5 g (997 mmol) of sodium tetraborate are dissolved in 1000 ml of THF and 600 ml of water, and degassed. 9.3 g (13.3 mmol) of bis(triphenylphosphine)palladium(II) chloride and 1 g (20 mmol) of hydrazinium hydroxide are added. The reaction mixture is then stirred under a protective gas atmosphere at 70 C. for 48 h. The cooled solution is supplemented with toluene, washed repeatedly with water, dried and concentrated. The product is purified via colunm chromatography on silica gel with toluene/heptane (1:2). Yield: 155 g (553 mmol), 83% of theory.
83%	With bis-triphenylphosphine-palladium(II) chloride; Sodium borate; hydrazine hydrate; In tetrahydrofuran; water; at 70℃; for 48h;Inert atmosphere;	200 g (664 mmol) of <strong>[450412-29-0]1-bromo-3-fluoro-2-iodobenzene</strong>, 101 g (664 mmol) of 2-methoxyphenylboronic acid and 137.5 g (997 mmol) of sodium tetraborate are dissolved in 1000 ml of THF and 600 ml of water, and degassed. 9.3 g (13.3 mmol) of bis(triphenylphosphine)palladium(II) chloride and 1 g (20 mmol) of hydrazinium hydroxide are added. The reaction mixture is stirred under a protective gas atmosphere at 70 C. for 48 h. The cooled solution is supplemented with toluene, washed repeatedly with water, dried and concentrated. The product is purified via column chromatography on silica gel with toluene/ heptane (1:2). Yield: 155 g (553 mmol), 83% of theory.

Reference： [1]Patent: KR2016/28524,2016,A .Location in patent: Paragraph 0232-0234
[2]Patent: WO2016/198144,2016,A1 .Location in patent: Page/Page column 53
[3]Patent: WO2017/71791,2017,A1 .Location in patent: Page/Page column 46-47
[4]Patent: TW2017/31839,2017,A .Location in patent: Page/Page column 51
[5]Patent: US2019/119260,2019,A1 .Location in patent: Paragraph 0114; 0118
[6]Patent: US2019/367494,2019,A1 .Location in patent: Paragraph 0107

51
[ 5720-06-9 ]
[ 50548-45-3 ]

Reference： [1]Patent: KR2016/28524,2016,A
[2]Patent: WO2016/198144,2016,A1
[3]Patent: WO2017/71791,2017,A1
[4]Patent: TW2017/31839,2017,A
[5]Patent: US2019/119260,2019,A1
[6]Patent: US2019/367494,2019,A1

52
[ 78071-37-1 ]
[ 5720-06-9 ]
C₁₃H₁₂O₃S [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 4129 - 4135

53
[ 103273-01-4 ]
[ 5720-06-9 ]
C₁₇H₂₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate monohydrate; palladium diacetate; In toluene; at 100℃; for 3h;	200 mL three-necked eggplant flask fully dried (condenser, three-way cock, To a magnetic stirring bar) was added 2-methoxyphenylboronic acid (Wako Pure Chemical Industries, Ltd.) (3.19 g, 10.5 mmol), (0.05 mmol) of <strong>[103273-01-4]2-bromo-4-tert-butylaniline</strong> (2.8 g, 10 mmol), palladium acetate (manufactured by Wako Pure Chemical Industries, Ltd.), 2-dicyclohexylphosphino-2',6-dimethoxybiphenyl (Manufactured by Sigma-Aldrich Japan Co., Ltd.) (0.041 g, 0.1 mmol) 6.9 g (30 mmol) of potassium phosphate monohydrate (manufactured by Wako Pure Chemical Industries, Ltd.) In addition, suspended in 20 mL of toluene (manufactured by Kanto Chemical Co., Ltd.) The reaction was carried out at 100 C. for 3 hours. To this reaction solution was added 50 mL of water, After extraction with toluene, the organic layer was dried with MgSO 4 (manufactured by Kanto Kagaku Co., Ltd.) The solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent; hexane (Manufactured by KANTO CHEMICAL CO., LTD.) / Ethyl acetate (manufactured by KANTO CHEMICAL CO., LTD.) = 9/1) to obtain 2.40 g (94%, light yellow liquid) of Compound

Reference： [1]Patent: JP5769443,2015,B2 .Location in patent: Paragraph 0155

54
[ 5720-06-9 ]
[ 162102-79-6 ]
C₁₆H₁₅NO₅ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7267 - 7283

55
[ 126728-20-9 ]
[ 5720-06-9 ]
C₁₄H₁₀ClN₃O [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 6368 - 6371

56
[ 126728-20-9 ]
[ 5720-06-9 ]
2-chloro-4-(2-methoxyphenyl)-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 6368 - 6371

57
[ 7089-68-1 ]
[ 5720-06-9 ]
[ 145578-47-8 ]

Reference： [1]ACS Catalysis,2017,vol. 7,p. 2607 - 2615

58
[ 5720-06-9 ]
[ 118289-17-1 ]
2-(2-methoxyphenyl)isonicotinaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73.6%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 92℃; for 3h;Inert atmosphere;	2-Bromopyridine-4-carbaldehyde (376 mg, 2.021 mmol), toluene (7 mL), K2C03 aqueous solution (2.76 g potassium carbonate dissolved in 10 mL of water, 2 mL), tetrakis(triphenylphosphine) in a 50 mL two-necked flask Palladium (45,2 mg, 0.04 mmol) was stirred under nitrogen at room temperature for 15 minutes, then 2-methoxyphenylboronic acid (407.6 mg, 2.682 mmol) in absolute ethanol (3 mL) was added and the reaction was heated at 92C. After 3 hours, the reaction system was poured into water and extracted with ethyl acetate. The ethyl acetate layers were combined, washed successively with water and saturated brine, dried over anhydrous sodium sulfate, suction-filtered, the filtrate was concentrated under reduced pressure, concentrate was separated and purified by column chromatography (petroleum ether: ethyl acetate = 6: 1) to give a white solid 406.2mg, yield 73.6%
73.6%		General procedure: To a 50 mL two-necked flask equipped with magnetic stirrer and condenser was added 2-bromopyridine (1.0 eq), Pd(PPh3)4 (5 mol%), K2CO3 solution (2.0 eq) and toluene under N2 at room temperture. After reacted for 15 min, a solution of the boronic acid (1.2 eq) in EtOH was then added. The reaction mixture was then heated to 95 C and reacted for 4 h. After cooling to room temperature, to the reaction mixture aqueous NH4Cl was added and extracted three times with EtOAc. The organic extracts were then combined, washed with brine, dried with MgSO4 and then concentrated under reduced pressure. The crude product was then purified by silica gel column chromatography(Petroleum ether/EtOAc) to give compounds 1 and 5

Reference： [1]Patent: CN107474011,2017,A .Location in patent: Paragraph 0026-0028
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 6000 - 6014

59
[ 5720-06-9 ]
[ 131001-86-0 ]
C₁₆H₁₆O₃ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 5791 - 5800

60
[ 57418-97-0 ]
[ 5720-06-9 ]
2-chloro-2'-methoxy-[1,1'-biphenyl]-4-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; at 100℃; for 2h;Inert atmosphere; Microwave irradiation;	<strong>[57418-97-0]3-chloro-4-bromobenzonitrile</strong> (300 mg, 1.39 mmol 1.0 equiv), 2-methoxyphenylboronic acid(211 mg, 1.39 mmol 1.0 equiv), Pd(PPh3)4 (0.05 equiv) and K2CO3 (2.0 equiv) were weighed into a microwave tube and solvated with DME (2 mL) and H2O (0.6 mL). The reaction mixture was degassed by bubbling nitrogen through the solution for 5 minutes and then heated to 100 C under microwave irradiation for 2 hours. The reaction was allowed to cool to room temperature, filtered through celite washing with Et2O and the solvent removed under reduced pressure. The residue was dissolved in CH2Cl2/H2O and extracted three times with CH2Cl2. The combined organic extracts were washed with a saturated aqueous solution of NaCl, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography (silica gel, 1:9 EtOAc:pet ether) to provide the title compound as a white solid (228 mg, 0.94 mmol, 67%)

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 3016 - 3020

61
[ 5720-06-9 ]
[ 5350-41-4 ]
[ 883-90-9 ]

Reference： [1]RSC Advances,2019,vol. 9,p. 5738 - 5741

62
[ 87864-14-0 ]
[ 5720-06-9 ]
N-[2-(diethylamino)ethyl]-2-(2-methoxyphenyl)quinoline-4-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 4074 - 4090

63
[ 19430-93-4 ]
[ 5720-06-9 ]
[ 1415225-22-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2019,vol. 17,p. 4317 - 4325

64
[ 28342-75-8 ]
[ 5720-06-9 ]
5-bromo-2,4-difluoro-2'-methoxy-1,1'-biphenyl [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2019,vol. 7,p. 7760 - 7767

65
[ 172921-33-4 ]
[ 5720-06-9 ]
4-chloro-2,5-difluoro-2’-methoxy-1,1’-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 30.0h;Reflux; Inert atmosphere;	Under nitrogen, <strong>[172921-33-4]1-bromo-4-chloro-2,5-difluorobenzene</strong> (12 g, 52.8 mmol),(2-methoxyphenyl) boronic acid (8.42 g, 55.4 mmol), and potassium carbonate (14.58 g, 106 mmol)Is dissolved in a mixture of toluene (100 ml) / water (20 ml),A colorless suspension was obtained. Tetrakis (triphenylphosphine) palladium (0) (0.544 g, 0.528 mmol)Was added to the reaction mixture all at once. Degas the reaction mixture,Heated to reflux under nitrogen for 16 hours.According to the results of gas chromatograph mass spectrometry (GCMS) analysis, the reaction was not completed. Therefore,> 7 g boronic acid as catalyst, 1 g K2CO3,And 0.6 g of Pd (PPh3) 4,The resulting mixture was degassed and refluxed for 14 hours under nitrogen.The reaction mixture is then cooled, the organic phase is separated off and evaporated,Purify by silica gel column chromatography eluting with heptane as a yellow oil,4-Chloro-2,5-difluoro-2'-methoxy-1,1'-biphenyl was obtained.(11.0 g, 82% yield).
82%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 30.0h;Inert atmosphere; Reflux;	<strong>[172921-33-4]1-Bromo-4-chloro-2,5-difluorobenzene</strong> (12 g, 52.8 mmol), (2-methoxyphenyl)boronic acid (8.42 g, 55.4 mmol), and potassium carbonate (14.58 g, 106 mmol) were dissolved in a toluene (100 ml)/ water (20 ml) mixture under nitrogen to give a colorless suspension. Tetrakis(triphenylphosphine)palladium(0) (0.544 g, 0.528 mmol) was added to the reaction mixture in one portion. The reaction mixture was degassed and heated to reflux under nitrogen for 16 h. Based on the results of gas chromatography-mass spectroscopy (GCMS) analysis the reaction was not complete. Thus, 7 g more boronic acid, 1 g of K2CO3, and 0.6 g of Pd(PPh3)4 as catalyst was added, and the resulting mixture was degassed and refluxed under nitrogen for 14 h. The reaction mixture was then cooled down and the organic phase was separated, evaporated, and purified by column chromatography on silica gel, eluted with heptanes to yield 4-chloro-2,5-difluoro-2?-methoxy-1,1?-biphenyl (11.0 g, 82% yield) as yellow oil.

Reference： [1]Patent: JP2019/127489,2019,A .Location in patent: Paragraph 0129; 0130
[2]Patent: US2019/233451,2019,A1 .Location in patent: Paragraph 0159; 0160

66
[ 156682-52-9 ]
[ 5720-06-9 ]
4-bromo-2,3-difluoro-2’-methoxy-1,1’-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 80℃; for 20h;	1,4-Dibromo-2,3-difluorobenzene (15 g, 55.2 mmol), (2-methoxyphenyl) boronic acid in a mixture of water (140 ml) and dioxane (140 ml)(8.80 g, 57.9 mmol), sodium carbonate(11.69 g, 110 mmol) and tetrakis(Triphenylphosphine) palladium (0)(3.19 g, 2.76 mmol) was dissolved.The reaction mixture was degassed and heated in an 80 C. oil bath for 20 hours. The reaction mixture is cooled to room temperature, mixed with brine,Extracted with EtOAc. Washing the extract with water and brine;Dry and evaporate to obtain a solid / liquid mixture,Adsorbed on a silica gel plug,Subjected to silica gel column chromatography,Elution with heptane as a colorless oil4-Bromo-2,3-difluoro-2'-methoxy-1,1'-biphenyl was obtained.(12.5 g, 75% yield).
75%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 80℃; for 20h;	<strong>[156682-52-9]1,4-dibromo-2,3-difluorobenzene</strong> (15 g, 55.2 mmol), (2-methoxyphenyl)boronic acid (8.80 g, 57.9 mmol), sodium carbonate (11.69 g, 110 mmol), and tetrakis(triphenylphosphine)palladium(0) (3.19 g, 2.76 mmol) were dissolved in a mixture of water (140 ml) and dioxane (140 ml). The reaction mixture was degassed and heated in an 80 C. oil bath for 20 h. The reaction mixture was cooled to room temperature, mixed with brine and extracted with EtOAc. The extract was washed with water, brine, dried, and evaporated to leave a solid/liquid mixture that was absorbed onto a silica gel plug and chromatographed on silica gel column eluted with heptane to yield 4-bromo-2,3-difluoro-2?-methoxy-1,1?-biphenyl as a colorless oil (12.5 g, 75% yield).

Reference： [1]Patent: JP2019/127489,2019,A .Location in patent: Paragraph 0144-0145
[2]Patent: US2019/233451,2019,A1 .Location in patent: Paragraph 0174; 0175

67
[ 5720-06-9 ]
[ 148639-07-0 ]
C₁₂H₉ClFNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 80℃; for 12h;Inert atmosphere;	To a three-necked flask was added <strong>[148639-07-0]2-chloro-3-fluoro-4-iodopyridine</strong> (30 g, 116.5 mmol), 2-methoxyphenylboronic acid (17.7 g, 116.5 mmol), 2M-potassium carbonate (under nitrogen). 250 mL) was dissolved in tetrahydrofuran (250 mL).Nitrogen was replaced for 30 minutes, and a catalyst tetrakistriphenylphosphine palladium (3 mol%) was added.The reaction system was warmed to 80 C and stirred under reflux for 12 hours.After cooling to room temperature, the reaction mixture was quenched with water and ethyl acetate and brine.Wash two to three times with saturated brine and take the organic phase.The organic phase was dried over anhydrous magnesium sulfate and concentrated.The intermediate I-1 (20.8 g, yield: 75%) was obtained by chromatography on silica gel chromatography.

Reference： [1]Patent: CN109988193,2019,A .Location in patent: Paragraph 0080-0082

68
[ 5720-06-9 ]
[ 39549-79-6 ]
2-(2-methoxyphenyl)-7-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

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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
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
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
H350	May cause cancer
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. 5720-06-9 ]

Quality Control of [ 5720-06-9 ]

Related Doc. of [ 5720-06-9 ]

Product Details of [ 5720-06-9 ]

Calculated chemistry of [ 5720-06-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 5720-06-9 ]

Application In Synthesis of [ 5720-06-9 ]

[ 5720-06-9 ] Synthesis Path-Upstream 1~21

[ 5720-06-9 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 5720-06-9 ]

Organoboron

Aryls

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 5720-06-9 ]