[ CAS No. 876189-18-3 ] {[proInfo.proName]}

Name: 876189-18-3|(5-(Methoxycarbonyl)-2-methylphenyl)boronic acid|98%
Brand: Ambeed
SKU: A139961
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Quality Control of [ 876189-18-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 876189-18-3 ]

SDS Specification

Alternatived Products of [ 876189-18-3 ]

Product Details of [ 876189-18-3 ]

CAS No. :	876189-18-3	MDL No. :	MFCD11111429
Formula :	C₉H₁₁BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PGNCKSWGMBDXGE-UHFFFAOYSA-N
M.W :	193.99	Pubchem ID :	12163650
Synonyms :

Calculated chemistry of [ 876189-18-3 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	52.51
TPSA :	66.76 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) :	-6.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.04
Log Po/w (WLOGP) :	-0.54
Log Po/w (MLOGP) :	0.52
Log Po/w (SILICOS-IT) :	-0.39
Consensus Log Po/w :	0.13

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.82
Solubility :	2.96 mg/ml ; 0.0152 mol/l
Class :	Very soluble
Log S (Ali) :	-2.03
Solubility :	1.8 mg/ml ; 0.00928 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.75
Solubility :	3.41 mg/ml ; 0.0176 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.0

Safety of [ 876189-18-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 876189-18-3 ]

* 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 [ 876189-18-3 ]
Downstream synthetic route of [ 876189-18-3 ]

[ 876189-18-3 ] Synthesis Path-Upstream 1~4

1
[ 90347-66-3 ]
[ 876189-18-3 ]

Reference： [1] Organic Letters, 2006, vol. 8, # 2, p. 305 - 307

2
[ 67-56-1 ]
[ 170230-88-3 ]
[ 876189-18-3 ]

Reference： [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 12, p. 3909 - 3913[2] Angew. Chem., 2016, p. 3977 - 3981,5
[3] Angewandte Chemie - International Edition, 2010, vol. 49, # 8, p. 1492 - 1495
[4] Patent: WO2014/144380, 2014, A1, . Location in patent: Page/Page column 110

3
[ 7697-26-9 ]
[ 876189-18-3 ]

Reference： [1] Patent: WO2014/144380, 2014, A1,

4
[ 876189-18-3 ]
[ 76-09-5 ]
[ 882679-40-5 ]

Reference： [1] Patent: WO2014/144380, 2014, A1, . Location in patent: Page/Page column 110

[ 876189-18-3 ] Synthesis Path-Downstream 1~62

1
[ 90347-66-3 ]
[ 876189-18-3 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 305 - 307

2
[ 876189-18-3 ]
[ 82827-09-6 ]
[ 1070292-54-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 95℃; for 12h;	6-Bromo-2W-isoquinolin-1~one (0.5g ) (intermediate 1 ), 3-borono-4-methyl-benzoic acid methyl ester (0.5g ) (intermediate 2 ), potassium carbonate (0.6g) , and dry DMF (1OmL) were stirred under nitrogen at room temperature.Tetrakis(triphenylphosphine)palladium(0) (200mg) was then added and the mixture heated at 950C for 12 hours. The mixture was allowed to cool to room temperature and then poured into dilute hydrochloric acid. The aqueous was extracted with ethyl acetate. The organics were combined, dried over magnesium sulfate then filtered and evaporated <n="83"/>under reduced pressure. Purification (SiO2 with 1 :1 ethyl acetate / isohexane eluant) gave the title compound (0.45g).MS: APCI (+ve) 294 (M+H}+ 1H NMR DMSOd6 11.30 (1 H, s broad), 8.25 (1 H, d), 7.96-7.85 (1 H, m), 7.72-7.48 (4H, m), 7.25 (1H, t), 6.62 (1H, d), 3.86 (3H, s), 2.33 (3H, s).

Reference： [1]Patent: WO2008/122765,2008,A1 .Location in patent: Page/Page column 81-82

3
[ 876189-18-3 ]
[ 1036712-58-9 ]
[ 1070292-87-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 95.0℃; for 17.0h;	A mixture of 6-bromo-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one (product of step iv) ) (1.2 g), intermediate 2 (0.7g), potassium carbonate (1.0 g) and tetrakis(triphenylphosphine)palladium(0) (0.4 g) in lambda/,lambda/-dimethylformamide (2OmL) was heated to 950C for 17 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic phase was dried, filtered and evaporated. The residue was purified (SiO2, 1 :2 ethyl acetate:iso-hexane as eluent) to yield the sub-titled compound (1.03g).MS: APCI(+ve) 414 [M+H]+

Reference： [1]Patent: WO2008/122765,2008,A1 .Location in patent: Page/Page column 103

4
[ 876189-18-3 ]
[ 126-30-7 ]
[ 1221343-13-0 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 1492 - 1495

5
[ 67-56-1 ]
[ 170230-88-3 ]
[ 876189-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid;Reflux;	To a stirred solution of SKC-01-126 (3.3 g, 18.3 mmol) in MeOH (100 ml) in a 250 ml round bottom flask fitted with a reflux condenser and drying guard tube was added 3 ml concentrated H2S04. The mixture was refluxed overnight. After cooling to room temperature, the solvent was evaporated in vacuum. Water was added and the product was extracted with ethyl acetate. The combined orgaric layers were washed with brine, dried over anhydrous MgSO4, filtered, and evaporated to dryness to give the methyl ester SKC-01-127 as a white solid. Without further purification, the methyl ester (4.00 g, 20.6 mmol) was dissolved in dry toluene (100 ml) in a 250 ml round bottom flask fitted with a Dean-stark trap. To the stirred reaction mixture, 2,3-dimethylbutane-2,3-diol (3.66 g, 30.9 mmol) was added followed by catalytic amount of p-TSOH.H20 (0.196 g, 1.03 mmol). The reaction mixture was heated to reflux overnight for 2 days. Water was collected (2 ml) and removed. After cooling,reaction mixture became solid. The crude product was purified using an ISCO system (80 g silica column, hexane/EtOAc gradient) to give SKC-ul-138. LCMS (M+H) 277. 1H NMR (400 MHz, CDC13) oe 8.32 (d, J= 1.9 Hz, 1H), 7.87 (dd, J 8.0,Hz, 1H), 7.12 (d,J 8.0 Hz, 1H), 3.79 (s, 3H), 2.48 (s, 3H), 1.25 (s, 1211).

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 3909 - 3913
Angew. Chem.,2016,p. 3977 - 3981,5
[2]Angewandte Chemie - International Edition,2010,vol. 49,p. 1492 - 1495
[3]Patent: WO2014/144380,2014,A1 .Location in patent: Page/Page column 110

6
[ 876189-18-3 ]
[ 847560-46-7 ]
C₁₈H₁₇N₃O₄S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2845 - 2850

7
[ 876189-18-3 ]
[ 106-38-7 ]
[ 1631032-52-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With tetrabutylammomium bromide; potassium carbonate; In water; at 80.0℃; for 12.0h;Green chemistry;	General procedure: Aryl halide (0.125 mmol), phenylboronic acid (0.15 mmol), K2CO3 (0.15 mmol) and n-Bu4NBr (0.15 mmol) were combined with 3 mL water in a small round-bottomed flask used for ?homogeneous? and ?heterogeneous? runs. The reaction mixture was stirred at 80C for 12 h, then, the mixture was acidified, and the product was extracted by ethyl ether for three times. The combined organic phase was dried with MgSO4, filtered, and solvent was removed on a rotary evaporator. Crude product was transferred into a 10 mL volumetric flask to fix its quantity in ethyl acetate. The yields were determined by high performance liquid chromatography (HPLC), based on the peak area ratio between the products. The HPLC conditions were a Zorbax eclipse Xdb C18 column (150 × 4.6 mm 5 mum) with methanol/acetonitrile as the mobile phase, and a flow rate of 1 mL/min.

Reference： [1]RSC Advances,2014,vol. 4,p. 26413 - 26420
[2]Journal of Molecular Catalysis A: Chemical,2014,vol. 395,p. 293 - 299

8
[ 876189-18-3 ]
[ 76-09-5 ]
[ 882679-40-5 ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In toluene; for 48.0h;Dean-Stark; Reflux;	To a stirred solution of SKC-01-126 (3.3 g, 18.3 mmol) in MeOH (100 ml) in a 250 ml round bottom flask fitted with a reflux condenser and drying guard tube was added 3 ml concentrated H2S04. The mixture was refluxed overnight. After cooling to room temperature, the solvent was evaporated in vacuum. Water was added and the product was extracted with ethyl acetate. The combined orgaric layers were washed with brine, dried over anhydrous MgSO4, filtered, and evaporated to dryness to give the methyl ester SKC-01-127 as a white solid. Without further purification, the methyl ester (4.00 g, 20.6 mmol) was dissolved in dry toluene (100 ml) in a 250 ml round bottom flask fitted with a Dean-stark trap. To the stirred reaction mixture, 2,3-dimethylbutane-2,3-diol (3.66 g, 30.9 mmol) was added followed by catalytic amount of p-TSOH.H20 (0.196 g, 1.03 mmol). The reaction mixture was heated to reflux overnight for 2 days. Water was collected (2 ml) and removed. After cooling, the reaction mixture became solid. The crude product was purified using an ISCO system (80 g silica column, hexane/EtOAc gradient) to give SKC-ul-138. LCMS (M+H) 277. 1H NMR (400 MHz, CDC13) oe 8.32 (d, J= 1.9 Hz, 1H), 7.87 (dd, J 8.0, 2.0 Hz, 1H), 7.12 (d,J 8.0 Hz, 1H), 3.79 (s, 3H), 2.48 (s, 3H), 1.25 (s, 1211).

Reference： [1]Patent: WO2014/144380,2014,A1 .Location in patent: Page/Page column 110

9
[ 7697-26-9 ]
[ 876189-18-3 ]

Reference： [1]Patent: WO2014/144380,2014,A1

10
[ 876189-18-3 ]
methyl 4-(bromomethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate [ No CAS ]

Reference： [1]Patent: WO2014/144380,2014,A1

11
[ 876189-18-3 ]
[ 1221343-14-1 ]

Reference： [1]Patent: WO2014/144380,2014,A1

12
[ 876189-18-3 ]
N’-(tert-butyl)-1-hydioxy-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbohyrazide [ No CAS ]

Reference： [1]Patent: WO2014/144380,2014,A1

13
[ 876189-18-3 ]
N-(tert-butyl)-N’-(3,5-dimethylbenzoyl)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborole-6-carbohydrazide [ No CAS ]

Reference： [1]Patent: WO2014/144380,2014,A1
[2]Patent: WO2014/144380,2014,A1

14
[ 876189-18-3 ]
C₁₉H₁₆O₂ [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,2015,vol. 88,p. 1726 - 1734

15
[ 876189-18-3 ]
C₂₂H₂₀O₂ [ No CAS ]
C₂₂H₂₀O₂ [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,2015,vol. 88,p. 1726 - 1734

16
[ 876189-18-3 ]
(±)-allyl 4-methyl-3-(2-methylnaphthalen-1-yl)benzoate [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,2015,vol. 88,p. 1726 - 1734

17
[ 876189-18-3 ]
C₁₉H₁₅ClO [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,2015,vol. 88,p. 1726 - 1734

18
[ 876189-18-3 ]
[ 2586-62-1 ]
C₂₀H₁₈O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; at 100.0℃; for 18.0h;Schlenk technique;	Process I: A 20- mL Schlenk flask was charged with [5-(methoxycarbonyl)-2- methylphenyl]boronic acid (200 mg, 1.03mmol),12 1-bromo-2- methylnaphthalene (80.0 L, 521 mol), 2.00M aq Na2CO3 (1.00 mL, 2.00mmol), and DME (4.00 mL). After degassing the whole mixture by three freeze-thaw cycles, to the suspension was added [Pd(PPh3)4] (60.0 mg, 51.9 mol). The mixture was heated at 100 C for 18 h. The reaction mixture was cooled to rt, and then the diphase solution was acidified by addition of 1M aq HCl (10 mL). This was extracted with CH2Cl2 (10mL 3), and the organic extracts were dried over Na2SO4 (ca. 5 g), filtered, and concentrated to give the crude product (0.3 g) as a yellow oil. This was used for the next reaction without further purification

Reference： [1]Bulletin of the Chemical Society of Japan,2015,vol. 88,p. 1726 - 1734

19
[ 876189-18-3 ]
(1R,2R,3S,5R)-2-(4-(2-(2-methoxyethoxy)ethoxy)butyl)-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol [ No CAS ]
methyl 3-((3aR,4R,6R,7aS)-3a-(4-(2-(2-methoxyethoxy)ethoxy)butyl)-5,5-dimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)-4-methylbenzoate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 3909 - 3913
Angew. Chem.,2016,p. 3977 - 3981,5

20
methyl 3-((3aR,4R,6R,7aS)-3a-(4-(2-(2-methoxyethoxy)ethoxy)butyl)-5,5-dimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)-4-methylbenzoate [ No CAS ]
[ 876189-18-3 ]
(1R,2R,3S,5R)-2-(4-(2-(2-methoxyethoxy)ethoxy)butyl)-6,6-dimethylbicyclo[3.1.1]heptane-2,3-diol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 3909 - 3913
Angew. Chem.,2016,p. 3977 - 3981,5

21
[ 876189-18-3 ]
[ 1834-27-1 ]
methyl 3-(3-chloro-5-methyl-6-oxopyridazin-1(6H)-yl)-4-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With pyridine; pyridine N-oxide; copper diacetate; In dichloromethane; at 20.0℃;	A solution of 6-chloro-4-methylpyridazin-3-ol (0.5 g, 3.5 mmol) in dichloromethane (20 mL, 3.4 mmol) was treated with (5-(methoxycarbonyl)-2- methylphenyl)boronic acid (1 g, 5.15 mmol), copper(II) acetate (1.25 g, 6.87 mmol), pyridine 1- oxide (33 mg, 3.44 mmol), and pyridine (1.1 g, 13.75 mmol). The resulting mixture was stirred overnight at RT. The mixture was diluted with DCM (100 mL) and washed with water (2 x 30 mL). The organic layer was separated, dried (Na2504), filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (Redi Sep 80 g) eluting with 2-55%EtOAc/hexane to provide methyl 3 -(3 -chloro-5 -methyl-6-oxopyridazin- 1 (6H)-yl)-4-methylbenzoate (430 mg, 43 % yield) as a solid. LCMS (APCI+) m/z 293.0 (M+1); retention time = 4.086 mm.

Reference： [1]Patent: WO2017/70708,2017,A1 .Location in patent: Paragraph 00588; 00589; 00590; 00591

22
[ 876189-18-3 ]
methyl 4-methyl-3-(5-methyl-6-oxo-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridazin-1(6H)-yl)benzoate [ No CAS ]

Reference： [1]Patent: WO2017/70708,2017,A1

23
[ 876189-18-3 ]
tert-butyl 4-(4-(5-amino-6-(1-(5-(methoxycarbonyl)-2-methylphenyl)-5-methyl-6-oxo-1,6-dihydropyridazin-3-yl)pyrazin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/70708,2017,A1

24
[ 876189-18-3 ]
3-(3-(3-amino-6-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-1H-pyrazol-4-yl)pyrazin-2-yl)-5-methyl-6-oxopyridazin-1(6H)-yl)-4-methylbenzoic acid [ No CAS ]

Reference： [1]Patent: WO2017/70708,2017,A1

25
[ 876189-18-3 ]
tert-butyl 4-(4-(5-amino-6-(5-methyl-1-(2-methyl-5-(methylcarbamoyl)phenyl)-6-oxo-1,6-dihydropyridazin-3-yl)pyrazin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2017/70708,2017,A1

26
[ 876189-18-3 ]
[ 1834-27-1 ]
methyl 3-(3-chloro-5-methyl-6-oxopyridazin-1(6H)-yl)-4-methylbenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With pyridine; pyridine N-oxide; copper diacetate; In dichloromethane; at 20℃;	A solution of 6-chloro-4-methylpyridazin-3-ol (Intermediate X17; 0.50 g, 3.4 mmol) in DCM (20 mL) was treated with <strong>[876189-18-3](5-(methoxycarbonyl)-2-methylphenyl)boronic acid</strong> (1.0 g, 5.2 mmol), Cu(OAc)2 (1.2 g, 6.9 mmol), pyridine 1-oxide (327 mg, 3.44 mmol) and pyridine (1.1 g, 14 mmol). The resulting mixture was stirred at ambient temperature open to the atmosphere for one overnight. The reaction mixture was diluted with DCM (100 mL) and washed with water (2 x 30 mL). The organic extracts were dried over anhydrous Na2SO4(), filtered and concentrated under vacuum. The crude residue was purified by silica gel flash chromatography (2-55% EtOAc/hexane as the gradient eluent) to afford the title compound (2.99 g, 99% yield). MS (apci) m/z = 293.0 (M+H), 295.0 [(M+H)+2] (with Cl pattern).

Reference： [1]Patent: WO2017/70708,2017,A1 .Location in patent: Paragraph 00557; 00558; 00559; 00560

27
[ 876189-18-3 ]
3-(4-bromoimidazol-1-yl)-5-methoxypyridine [ No CAS ]
methyl 3-[1-(5-methoxy-3-pyridyl)imidazol-4-yl]-4-methyl-benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.1 g	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 130.0℃; for 0.5h;Sealed tube; Inert atmosphere; Microwave irradiation;	Intermediate 1-22-1 (0.20 g, 0.79 mmol), (5-methoxycarbonyl-2-methyl-phenyl)boronic acid (0.153 g, 0.787 mmol), tetrakis (triphenylphosphine)palladium (0) (45.5 mg, 0.039 mmol), and sodium carbonate (0.250 g, 2.36 mmol), are combined with 2 mE of 1,4-dioxane and 1 mE water are combined in a microwave vial that is sealed and purged with argon. The reaction is heated at 130 C. in a microwave reactor for 30 mm. The reaction is concentrated under reduced pressure and the residue diluted with EtOAc and water causing a solid to precipitate from solution. The formed solid is collected by filtration and dried to afford 0.100 g of methyl 3-[ 1 -(5-methoxy-3-pyridyl)imidazol-4- yl] -4-methyl-benzoate (1-22-2).

Reference： [1]Patent: US2018/72703,2018,A1 .Location in patent: Paragraph 0276; 0281

28
[ 876189-18-3 ]
[ 52200-48-3 ]
methyl 3-(2-chloropyridin-3-yl)-4-methylbenzoate [ No CAS ]