876189-18-3|(5-(Methoxycarbonyl)-2-methylphenyl)boronic acid| Ambeed

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Quality Control of [ 876189-18-3 ] Purity: 98% SDS Specification

COA

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NMR

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Product Details of [ 876189-18-3 ]

CAS No. :	876189-18-3
Formula :	C₉H₁₁BO₄
M.W :	193.99
SMILES Code :	OB(C1=CC(C(OC)=O)=CC=C1C)O
MDL No. :	MFCD11111429
InChI Key :	PGNCKSWGMBDXGE-UHFFFAOYSA-N
Pubchem ID :	12163650

Safety of [ 876189-18-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 876189-18-3 ] Show Less

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 ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.76 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.04
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.54
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.52
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.39
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.13

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.82
Solubility	2.96 mg/ml ; 0.0152 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.03
Solubility	1.8 mg/ml ; 0.00928 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.75
Solubility	3.41 mg/ml ; 0.0176 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.74 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.0

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 1~3

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

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

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

References: [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 ]

References: [1] Patent: WO2014/144380, 2014, A1, .

[ 876189-18-3 ] Synthesis Path-Downstream 1~35

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

References: [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 95.0℃; for 12.0h;	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).

References: [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]+

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

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

References: [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).

References: [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 ]

References: [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.

References: [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).

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

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

References: [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 ]

References: [1]Patent: WO2014/144380,2014,A1 .

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

References: [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 ]

References: [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 ]

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

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

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

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

References: [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 ]

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

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

References: [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

References: [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 ]

References: [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 ]

References: [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.

References: [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 ]

References: [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 ]

References: [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 ]

References: [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 ]

References: [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 20.0℃;	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).

References: [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).

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

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