882679-40-5|Methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate| Ambeed

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Quality Control of [ 882679-40-5 ] Purity: 95% SDS Specification

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Product Details of [ 882679-40-5 ]

CAS No. :	882679-40-5
Formula :	C₁₅H₂₁BO₄
M.W :	276.14
SMILES Code :	O=C(OC)C1=CC=C(C)C(B2OC(C)(C)C(C)(C)O2)=C1
MDL No. :	MFCD11520530
InChI Key :	HAPIXNBOBZHNCA-UHFFFAOYSA-N
Pubchem ID :	53217136

Safety of [ 882679-40-5 ]

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

Computational Chemistry of [ 882679-40-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	20
Num. arom. heavy atoms	6
Fraction Csp3	0.53
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	79.16
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	44.76 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	3.13
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.08
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.	1.79
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	2.29
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.86

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.55
Solubility	0.0782 mg/ml ; 0.000283 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.74
Solubility	0.0503 mg/ml ; 0.000182 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	-4.46
Solubility	0.0096 mg/ml ; 0.0000348 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	Yes
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	Yes
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.	-5.76 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	0.0
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<0.0
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)	3.22

Application In Synthesis of [ 882679-40-5 ]

* 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.

Downstream synthetic route of [ 882679-40-5 ]

[ 882679-40-5 ] Synthesis Path-Downstream 1~35

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References: [1]Chemistry Letters,2011,vol. 40,p. 962 - 963.
[2]Chemistry Letters,2011,vol. 40,p. 962 - 963.

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References: [1]Patent: WO2011/109277,2011,A1 .

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References: [1]Patent: WO2011/109277,2011,A1 .

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References: [1]Patent: WO2011/109277,2011,A1 .

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References: [1]Patent: WO2011/109277,2011,A1 .

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References: [1]Patent: WO2011/109277,2011,A1 .

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Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl;palladium diacetate; In tetrahydrofuran; water; at 75℃; for 14h;	5-chloro-l -[(2,2-difluorocyclopropyl)methyl]-3-methyl- 1 ,3-dihydro[ 1 ,2,5] thiadiazolo[3,4-b]pyridine 2,2-dioxide (29-1) (6.6 g, 21.3 mmol, 1.0 eq), methyl 4-methyl-3- (4,4,5,5-tetramethyl-1,3 ,2-dioxaborolan-2-yl)benzoate (8.8 g, 32.0 mmol, 1.5 eq), tripotassium phosphate (9.0 g, 42.6 mmol, 2.0 eq), S-Phos (875 mg, 2.1 mmol, 0.1 eq), and palladium(II) acetate (239 mg, 1.1 mmol, 0.05 eq) were combined in THF (90 mL) and water (15 mL). The resulting mixture was heated at 75 C for 14 hours. The reaction mixture was allowed to cool to room temperature. The mixture was then diluted with EtOAc (300 mL), washed with water (100 mL) and brine (100 mL), dried over MgS04, filtered and concentrated. The crude residue was purified by flash chromatography (330 g Si02, 0-60% EtOAc in hexanes) to afford methyl 3-{l- [(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro[1,2,5]thiadiazolo[3,4- b]pyridin-5-yl}-4-methylbenzoate (38-1) as a yellow solid. HRMS m/z (M+H) 424.1135 found, 424.1137 required.

References: [1]Patent: WO2011/109277,2011,A1 .Location in patent: Page/Page column 88.

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[ 1221343-14-1 ]

References: [1]Chemical Communications,2012,vol. 48,p. 4115 - 4117.
[2]Patent: WO2014/144380,2014,A1 .

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Yield	Reaction Conditions	Operation in experiment
84%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 16h;Inert atmosphere;	Methyl 3-bromo-4-methylbenzoate (3 mL, 19.2 mmol) was dissolved in 1,4-dioxane (96 mL), and bis(pinacolato)diboron (7.31 g, 28.2 mmol), potassium acetate (5.65 g, 57.6 mmol), and Pd(dppf)Cl2 (2.8 g, 3.84 mmol) were added thereto. The resulting mixture was replaced with argon, and stirred at 90C for 16 hours. The mixture was cooled to room temperature, and water was added. Then, the mixture was extracted with EtOAc. An organic layer was dried over magnesium sulfate, concentrated, and then purified using silica gel chromatography to obtain the title compound (off-white solid, 4.46 g, and 84% yield). 1H NMR (300 MHz, CDCl3) delta 8.40 (d, 1H), 7.97 (dd, 1H), 7.23 (d, 1H), 3.94-3.87 (m, 3H), 2.58 (s, 3H), 1.35 (d, 12H).

References: [1]Chemical Communications,2012,vol. 48,p. 4115 - 4117.
[2]Patent: EP2963027,2016,A1 .Location in patent: Paragraph 0470; 0471; 0472.
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 4869 - 4881.

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References: [1]Chemical Communications,2012,vol. 48,p. 8273 - 8275.

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[ 1459216-73-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In 1,4-dioxane; water; at 120℃; for 0.5h;Microwave irradiation;	A mixture of (R)-6-bromo-N2-(1-(4-chlorophenyl)ethyl)pyrazine-2,3-diamine (325 mg, 1.0mmol), <strong>[882679-40-5]methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate</strong> (357 mg, 1.3mmol), Pd(dppf)Cl2 (73 mg, 0.1 mmol), and Cs2CO3 (650 mg, 2 mmol) in 1,4-dioxane (3.0 mL)and H2O (1.0 mL) was heated under microwave irradiation at 120 C for 30 min. The solid was removed via filtration and the solution was partitioned between H2O (5 mL) and EtOAc (20 mL).The EtOAc layer was concentrated and purified by column chromatography (50% EtOAc inpetroleum ether) and provided the title compound (340 mg, 86% yield).

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 5533 - 5539.

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Yield	Reaction Conditions	Operation in experiment
65%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; at 90℃; for 18h;Inert atmosphere;	Compound 7.1. Methyl 4-methyl-3-(2-methyl-lH-imidazol-5-yl)benzoate. To a solution of methyl 4-methyl-3-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 600 mg, 2.17 mmol) in dioxane (20 mL) was added 2-methyl-4-bromo imidazole (419 mg, 2.6 mmol), Pd(dppi)Cl2*CH2Cl2 (180 mg, 0.22 mmol). The mixture was degassed argon and stirred for 10 minutes then aqueous potassium carbonate (1M, 10 mL, 10 mmol) was added and the mixture was stirred at 90 C for 18 h. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc and filtered through Celite. The organic phase was washed by brine, dried (MgSC>4), filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (0-5 % MeOH in EtOAc) to yield the title compound as a foam (324 mg, 65%). m/z (ES+) 231 (M+H)+. NMR (400 MHz, CDC13) delta 8.30 (br s, 1H), 7.86 (dd, J= 7.9, 1.9 Hz, 1H), 7.32 (d, J= 7.9 Hz, 1

References: [1]Patent: WO2014/8197,2014,A1 .Location in patent: Page/Page column 77.

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Yield	Reaction Conditions	Operation in experiment
41%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 18h;Inert atmosphere;	Compound 51.1. Methyl 4-methyl-3-(lH-pyrazoI-5-yl)benzoate. To methyl 4- methyl-3-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 800 mg, 2.9 mmol) in dioxane (30 mL) was added 5-iodo-lH-pyrazole (674 mg, 3.5 mmol), and Pd(dppf)Cl2 FontWeight="Bold" FontSize="10" DCM (237 mg, 0.29 mmol). The mixture was degassed with argon and stirred for 10 minutes then an aqueous potassium carbonate solution (2 M, 8 mL) was added. The mixture was heated at 90 C for 18 h, then cooled and diluted with EtOAc and filtered through Celite. The filtrate was washed with brine, dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (Si02; 0-30 % EtOAc in hexanes) to yield 258 mg (41 %) of the title compound as a solid. m/z
41%		Compound 51.1. Methyl 4-methyl-3-(lH-pyrazol-5-yl)benzoate. To methyl 4- methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (compound 5.4, 800 mg, 2.9 mmol) in dioxane (30 mL) was added 5-iodo-lH-pyrazole (674 mg, 3.5 mmol), and Pd(dppf)Cl2 DCM (237 mg, 0.29 mmol). The mixture was degassed with argon and stirred for 10 minutes then an aqueous potassium carbonate solution (2 M, 8 mL) was added. The mixture was heated at 90 C for 18 h, then cooled and diluted with EtOAc and filtered through Celite. The filtrate was washed with brine, dried (MgSC^), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (S1O2; (M0-30 % EtOAc in hexanes) to yield 258 mg (41 %) of the title compound as a solid, m/z (ES+) 217 (M-H)+

References: [1]Patent: WO2014/8197,2014,A1 .Location in patent: Page/Page column 120.
[2]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 135; 136.

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Yield	Reaction Conditions	Operation in experiment
71%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃;Inert atmosphere;	Compound 5.4. Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate. A mixture of methyl 3-iodo-4-methylbenzoate (compound 5.3, 5.00 g, 18.1 mmol), 4,4,4',4',5,5,5',5,-octamethyl-2,2'-bi(l ,3,2-dioxaborolane) (5.20 g, 20.5 mmol), KOAc (5.33 g, 54.3 mmol) and PdCl2(dppf CH2Cl2 (0.74 g, 0.91 mmol) in DMSO (50 mL) was degassed with argon. The mixture was then heated at 80 C under argon overnight. The mixture was allowed to cool then partitioned between EtOAc (400 mL) and water (80 mL). The organic phase was washed with water (80 mL), saturated aqueous NaHC03 (80 mL), brine (80 mL), dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified with silica gel chromatography (hexanes: EtOAc 20: 1) to yield the title compound as a white crystalline solid (3.56 g, 71 %). NMR (400 MHz, CDC13) 5 8.41 (d, J = 1.9 Hz, 1 H), 7.97 (dd, J= 8.0 Hz, 2.0Hz, 1H), 7.23 (d, J= 8.0 Hz, 1H), 3.90 (s, 3H), 2.58
71%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃;Inert atmosphere;	Compound 5.4. Methyl 4-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate. A mixture of methyl 3-iodo-4-methylbenzoate (compound 5.3, 5.00 g, 18.1 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (5.20 g, 20.5 mmol), KOAc (5.33 g, 54.3 mmol) and PdCi2(dppf CH2Ci2 (0.74 g, 0.91 mmol) in DMSO (50 mL) was degassed with argon. The mixture was then heated at 80 C under argon overnight. The mixture was allowed to cool then partitioned between EtOAc (400 mL) and water (80 mL). The organic phase was washed with water (80 mL), saturated aqueous aHC03 (80 mL), brine (80 mL), dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified with silica gel chromatography (hexanes: EtOAc 20: 1) to yield the title compound as a white crystalline solid (3.56 g, 71%). NMR (400 MHz, CDC13) delta 8.41 (d, J= 1.9 Hz, 1H), 7.97 (dd, J= 8.0 Hz, 2.0Hz, 1H), 7.23 (d, J= 8.0 Hz, 1H), 3.90 (s, 3H), 2.58 (s, 3H), 1.35 (s, 12H).

References: [1]Patent: WO2014/8197,2014,A1 .Location in patent: Page/Page column 71; 72.
[2]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 86.

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