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1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one

CAS No.: 1002309-52-5

Category Products

Cat.NO.:A135180 Purity:98%

Product Details of [ 1002309-52-5 ]

CAS No. :	1002309-52-5
Formula :	C₁₂H₁₈BNO₃
M.W :	235.09
SMILES Code :	O=C1C=CC(B2OC(C)(C)C(C)(C)O2)=CN1C
MDL No. :	MFCD11044683
InChI Key :	IJUNZKOKAXJGRQ-UHFFFAOYSA-N
Pubchem ID :	45480194

Safety of [ 1002309-52-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 1002309-52-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	6
Fraction Csp3	0.58
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	68.44
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	40.46 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	0.93
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.68
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.	0.73
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	0.88
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.65

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.08
Solubility	1.96 mg/ml ; 0.00834 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.	-1.37
Solubility	10.1 mg/ml ; 0.0431 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-3.1
Solubility	0.187 mg/ml ; 0.000794 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	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.	-7.07 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<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)	2.97

Application In Synthesis of [ 1002309-52-5 ]

* 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 [ 1002309-52-5 ]

[ 1002309-52-5 ] Synthesis Path-Downstream 1~35

1
[ 81971-39-3 ]
[ 73183-34-3 ]
[ 1002309-52-5 ]

Yield	Reaction Conditions	Operation in experiment
23.6%	With (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 2h;Microwave irradiation;	A solution of 5-bromo-1-methylpyridin-2-one (200.0 mg, 1.06 mmol), bis(pinacolato)diboron (410.0 mg, 1.61 mmol), potassium acetate (270 mg, 2.67 mmol), Pd (dppf)Cl2 (80 mg, 0.11 mmol) in dioxane (5 mL) was heated at 100° C. for 2 h under microwave. The mixture was filtered, washed with water and extracted with ethyl acetate (20 mL*3). The combined organics were dried over Na2SO4, filtered and concentrated to give the crude title compound (59.0 mg, 23.6percent). LCMS (M+H)+ 236.
	With potassium acetate;dichloro(1,1′-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dimethyl sulfoxide; at 80℃; for 0.5h;	To a solution of 5-bromo-1-methylpyridin-2(1H)-one (800 mg) in DMSO (21 ml) was added bis(pinacolato)diboron (1620 mg), potassium acetate (1253 mg) and 1,1′-bis(diphenyl-phosphino)ferrocene-palladium(II)dichloride dichloromethane adduct (213 mg). The reaction mixture was stirred at 80°C for 30 min. The reaction was diluted with water (20 ml) and extracted with EtOAc (3 x 30 ml). The organic layer was dried with Na2SO4 and solvents were reduced under reduced pressure. The crude product was purified by flash chromatography.
	With sodium acetate;dichloro(1,1′-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 120 – 130℃; for 8.5h;	5-Bromo-l-methylpyridin-2 (IH) -one (0.100 g, 0.532 mmol) was suspended in dioxane (2 mL) then added 4,4,5,5- tetramethyl-2- (4,4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) – 1, 3, 2-dioxaborolane (0.203 g, 0.798 mmol), PdC12 (dppf) – CH2C12Adduct (0.0217 g, 0.0266 mmol) and sodium acetate (0.109 g, 1.33 mmol) . The reaction mixture was heated at 120 0C for 5.5 hours then at 130 0C for 3 hours. The reaction mixture was <n=”119″/>filtered through a pad of Celite, washing with MeOH. The filtrate was concentrated under vacuum. The remaining black residue was then dissolved in dichloromethane and filtered through another pad of Celite, washing well with dichloromethane. The filtrate was concentrated under vacuum and the remaining black residue was further dried under high vacuum to afford l-methyl-5- (4,4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2- yl)pyridin-2 (IH) -one as a black solid. MS (ESI pos. ion) m/z: 236.1 (MH+).

	With potassium acetate;palladium bis[bis(diphenylphosphino)ferrocene] dichloride; In dichloromethane; N,N-dimethyl-formamide; at 80℃; for 10h;	Example 9N-(3-fluoro-4-(l-methyl-6-oxo-l,6-dihvdropyridin-3-yl)benzyl)-4-(pyrazin-2-yl)benzamideCompound 21[0174] Step 1: A mixture of 5-bromo-l-methylpyridin-2(lH)-one 21-1 (350 mg, 1.87 mmol), (4,4′,4′,5,5,5′,5′-heptamethyl-[2,2′-bi(l,3,2-dioxaborolan)]-4-yl)methylium 21-2 (617 mg, 2.43 mmol), potassium acetate (550 mg, 5.61 mmol) and Pd(dppf)2Cl2 dichloromethane complex (82 mg, 0.1 mmol) in DMF (10 mL) was stirred at 80 °C for 10 hours. After cooling to room temperature, the mixture was filtered through celite, concentrated by evaporation under reduced pressure and then redistributed between ethyl acetate and water. The organic phase was dried over Na2S04 and concentrated by evaporation under reduced pressure. The resulting residue was subjected to silica gel column chromatography with 1: 1 ethyl acetate/hexanes as eluent to give l-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2(lH)-one 21-3.
	With potassium acetate;dichloro(1,1′-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 115℃;Inert atmosphere; Reflux;	Preparation of Compound 2222a 22b To a dry flask was added 5-bromo-l-methylpyridin-2(lH)-one 22a (1.0 g, 5.32 mmol), potassium acetate (1.57 g, 15.96 mmol, 3.0 equiv), bis(pinacolato)diboron (1.49 g, 5.85 mmol, LI equiv) and 1,4-dioxane (25 mL). Nitrogen was bubbled through the solution for 10 minutes, at which time dichloro[l,l’-bis(diphenylphosphino)ferrocene] palladium (II) dichloromethane adduct (217 mg 0.27 mmol, 0.05 equiv) was added. The reaction mixture was refluxed at 115 °C overnight under nitrogen. After cooling to room temperature, EtOAc (30 mL) was added and the resulting slurry was sonicated and filtered. Additional EtOAc (20 mL) was used to wash the solids. The combined organic extracts was concentrated and purified by flash chromatography (90percent EtOAc/ hexanes) to yield 22b (520 mg).Compound 22 was prepared analogous to the preparation of 2 but using compound 22b.
	With dichloro(1,1′-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 110℃; for 0.5h;	General procedure: A mixture of 3-bromo-1-methylpyridin-2(1H)-one (Step 1 of Example 25, 770 mg, 4.1 mmol),bis(pinacolato)diboron (1248 mg, 4.91 mmol), PdCI2(dppf)CH2CI2 complex (401 mg, 0.491mmol) and potassium acetate (1206 mg, 12.29 mmol) in dioxane (16 mL) was stirred for 2 h at 110 00. The reaction mixture was diluted with toluene, sonicated for 30 mm at 40°C and filtered (the filter cake was rinsed with hot toluene). The filtrate was concentrated to afford the title compound (1.7 g, purity 40percent) as a brown oil. The title compound was prepared using an analogous procedure to that described in Step 2 of Example 25 using 5-bromo-1-methylpyridin-2(1H)-one (ABCR, 1.05 g, 5.58 mmol) and stirringthe reaction mixture for 30 mm at 110°C. The title compound (2.75 g, purity 30percent) was used without purification. Rt: 0.83 mm (LC-MS 1); MS m/z: 236.2 [M+H] (boronic acid) (LC-MS 1).
160 mg	With (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In ethylene glycol; at 80℃; for 3h;	To a stirred suspension of 5-bromo-l-methylpyridin-2(lH)-one (470 mg, 2.49 mmol), potassium acetate (736 mg, 7.49 mmol) and bis(pinacolato)diboron (952 mg, 3.74 mmol) in degassed polyethylene glycol-400 (15 mL) was added [1, 1 ‘- bis(diphenylphosphino)ferrocene]dichloropalladium (II) (204 mg, 0.24 mmol) at RT. The resultant suspension was stirred for 3 h at 80 °C. The reaction mixture was cooled to RT, diluted with ethyl acetate (100 mL) and washed with water (100 mL) followed by brine (100 mL). The organic layer was concentrated and the residue obtained purified by flash column chromatography to afford 160 mg of the titled product; 1H NMR (300 MHz, CDC13) delta 1.30 (s, 12H), 3.54 (s, 3H), 6.53 (d, J = 9.3 Hz, 1H), 7.60 (d, J = 9.0 Hz, 1H), 7.75 (s, 1H); APCI- MS (m/z) 236 (M+H)+.

References: [1]Patent: US2015/111885,2015,A1 .Location in patent: Paragraph 0574; 0575.
[2]Patent: EP2168965,2010,A1 .Location in patent: Page/Page column 33.
[3]Patent: WO2008/8539,2008,A2 .Location in patent: Page/Page column 117-118.
[4]Patent: WO2012/3189,2012,A1 .Location in patent: Page/Page column 81.
[5]Patent: WO2011/60235,2011,A1 .Location in patent: Page/Page column 22.
[6]Patent: WO2015/75665,2015,A1 .Location in patent: Page/Page column 85; 108.
[7]Patent: WO2017/21879,2017,A1 .Location in patent: Page/Page column 64.
[8]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2993 – 2997.

2
[ 445264-61-9 ]
[ 74-88-4 ]
[ 1002309-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 80℃; for 3h;	X. l-Methyl-5-(4,4,5,5-tetramethyl-L3,2-dioxaborolan-2-yl)pyridin-2(lH)-one; A mixture of 2-methoxy-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridine(235 mg, 1.00 mmol) and CH3I (426 mg, 3.00 mmol) was heated at 800C for 3 hours. The mixture was partitioned between ethyl acetate and H2O. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over MgSO4, and evaporated to dryness to afford l-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridin-2(lH)-one that was directly used in next step without further purification.

References: [1]Patent: WO2008/141119,2008,A2 .Location in patent: Page/Page column 96-97.

3
[ 936727-68-3 ]
[ 1002309-52-5 ]
[ 1083167-72-9 ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 120℃; for 0.5h;microwave irradiation;	AO. l-(2.2-Difluorobenzordipi.31dioxol-5-yl)-N-(5-methyl-6-(l-methyl-6-oxo-L6-dihvdropyridin-3-yl)pyridin-2-yl)cvclopropanecarboxamide; To a mixture of l-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)pyridin-2(lH)-one (68 mg, 0.30 mmol), N-(6-chloro-5-methylpyridin-2-yl)-l-(2,2- difluorobenzo[d][l,3]dioxol-5-yl)cyclopropanecarboxamide (88 mg, 0.24 mmol) in DME (1.5 mL) and 2 M Na2CO3 (0.24 mL) was added Pd(PPh3)4 (14 mg, 0.0030 mmol). The mixture was heated in microwave oven at 1200C for 30 min. The mixture was partitioned between ethyl acetate and H2O before the aqueous layer was extracted with ethyl acetate (3x). The combined <n=”120″/>organic layers were washed with brine and dried over MgSO4. After the removal solvent, the residue was purified by column chromatography (10-20percent EtOAc -Hexane) to afford l-(2,2- difluorobenzo[d][l,3]dioxol-5-yl)-N-(5-methyl-6-(l-methyl-6-oxo-l,6-dihydropyridin-3- yl)pyridin-2-yl)cyclopropanecarboxamide (67 mg, 72percent). 1H-NMR (400 MHz, CDCl3) delta 8.06 (d, J = 8.4 Hz, IH), 7.63 (s, IH), 7.57 (d, J = 8.4 Hz, IH), 7.53-7.48 (m, 2H), 7.24 (td, J = 10.0, 1.7 Hz, 2H), 7.12 (d, J = 8.2 Hz, IH), 6.61 (d, J = 9.2 Hz, IH), 3.60 (s, 3H), 2.33 (s, 3H), 1.77 (q, J = 3.6 Hz, 2H), 1.19 (q, J = 3.6 Hz, 2H). MS (ESI) m/e (M+H+) 440.2.

References: [1]Patent: WO2008/141119,2008,A2 .Location in patent: Page/Page column 118-119.

4
[ 64-18-6 ]
[ 1002309-52-5 ]
[ 1162202-99-4 ]
[ 1347541-58-5 ]

Yield	Reaction Conditions	Operation in experiment
		A degassed mixture of 2-bromo-3-(3-pyrrolidin-1-yl-prop-1-ynyl)-imidazo[1,2-a]pyridine-6-carboxylic acid bis-(3-methyl-butyl)amide (200 mg), intermediate 33a) (145 mg), and 2M aqueous sodium carbonate solution (0.8 ml) in DMF (4 ml) was treated with Pd(PPh3)4 (47.3 mg). The reaction mixture was transferred to a pre-heated oil bath (110°C) and stirred in a sealed tube at this temperature overnight. The mixture was diluted with diethyl ether (50 ml) and washed with water (1 x 20 ml). The aqueous layer was extracted with diethyl ether (2 x 20 ml). The combined organic extract was washed with brine (50 ml), dried over sodium sulfate, filtered, and evaporated. The crude product was purified by column chromatography followed by preparative LC-MS.

References: [1]Patent: EP2168965,2010,A1 .Location in patent: Page/Page column 33.

5
[ 1002309-52-5 ]
[ 1225059-25-5 ]
[ 1225059-95-9 ]

Yield	Reaction Conditions	Operation in experiment
40%	With potassium carbonate;(1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 110℃; for 2h;	Example 11 : 5-(5-amino-6-(l-methyl-lH-benzo[dlimidazo Details Products CAS 53-59-8 Read more Products CAS 53-57-6 Read more Products CAS 57-22-7 Read more Reviews There are no reviews yet. Be the first to review “1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one” Cancel reply Your email address will not be published. Required fields are marked * Your rating * Your review * Name * Email * Save my name, email, and website in this browser for the next time I comment. Previous 1-Cyclobutyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole Next (2-Iodophenyl)(trifluoromethyl)sulfane Easy CDMO Easy CDMO is China TOP100 CDMO company. We believe: Easy CDMO, Medicinal Chemical is Big. More than 100 scientists are serving you. Quick Links About Us Products Blog Contacts Support Links Privacy Policy Term And Condition Locations Office address: Chenxun Technology Building, No. 633, Jinzhong Road, Changning District, Shanghai info@easycdmo.com +8602161734564 © Copyright Easy CDMO 2025. All Rights Reserved.