[ CAS No. 1692-25-7 ] {[proInfo.proName]}

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Quality Control of [ 1692-25-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1692-25-7 ]

Product Citations

Electrostatically Enhanced 3-and 4-Pyridyl Borate Salt Nucleophiles and Bases

Stephen H. Dempsey ; Alex Lovstedt ; Steven R. Kass JOC,2023,88(15):10525-10538. DOI: 10.1021/acs.joc.3c00523 PubMed ID: 37462157

Abstract: A variety of electrostatically enhanced 3- and 4-pyridylborate salt catalysts are reported and show significant improvement over an activated noncharged neutral control compound. Their nucleophilicity in a stoichiometric SN2 reaction and catalytic performance in a urethane synthesis are evaluated along with three methods for rapidly evaluating the basicity of these species. That is, qualitative titrations in CH2Cl2 and CHCl3 were carried out, two separate solution-state IR studies in CCl4 and CDCl3 are reported, and the proton affinities of the anionic components of the salts were computed. Charge differences between the anion and its protonated zwitterionic conjugate acid are evaluated along with the highest occupied molecular orbitals of the anions in relationship to some of the surprising reactivity findings that were observed in the two kinetic studies.

Purchased from AmBeed: 1692-15-5 ; 1692-25-7

Product Details of [ 1692-25-7 ]

CAS No. :	1692-25-7	MDL No. :	MFCD00674177
Formula :	C₅H₆BNO₂	Boiling Point :	-
Linear Structure Formula :	B(OH)₂C₅NH₄	InChI Key :	ABMYEXAYWZJVOV-UHFFFAOYSA-N
M.W :	122.92	Pubchem ID :	2734378
Synonyms :

Calculated chemistry of [ 1692-25-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	34.06
TPSA :	53.35 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) :	-7.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-0.24
Log Po/w (WLOGP) :	-1.24
Log Po/w (MLOGP) :	-1.39
Log Po/w (SILICOS-IT) :	-1.15
Consensus Log Po/w :	-0.81

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.88
Solubility :	16.3 mg/ml ; 0.132 mol/l
Class :	Very soluble
Log S (Ali) :	-0.42
Solubility :	46.5 mg/ml ; 0.378 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.87
Solubility :	16.6 mg/ml ; 0.135 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.85

Safety of [ 1692-25-7 ]

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

Applications of [ 1692-25-7 ]

Pyridin-3-ylboronic acid (CAS: 1692-25-7) can be used in the preparation of Nilotinib (AMN-107) (CAS: 641571-10-0). Nilotinib, also known as AMN107, is a tyrosine kinase inhibitor.

Application In Synthesis of [ 1692-25-7 ]

* 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 [ 1692-25-7 ]

[ 1692-25-7 ] Synthesis Path-Downstream 1~8

1
[ 13195-50-1 ]
[ 1692-25-7 ]
[ 837376-40-6 ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 224 - 239

2
[ 3934-20-1 ]
[ 1692-25-7 ]
[ 483324-01-2 ]

Yield	Reaction Conditions	Operation in experiment
74.6%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; water; at 90℃; for 4h;Inert atmosphere; Green chemistry;	In a 250 mL three-necked flask,2,4-dichloropyrimidine (5.0 g, 33.56 mmol)Dissolved in 1,4-dioxaneAnd water (4: 1, 50 mL) A solution of 3-boronic acid pyridine (4.95 g, 40.27 mmol),Potassium carbonate (9.28 g, 67.12 mmol)And Pd (dppf) Cl2 (2.45 g, 3.36 mmol);The system was replaced with argon three times,Gradually heated to 90 C,Reaction for 4 hours;After the reaction, the system was concentrated under reduced pressure to remove most of the solvent,Ethyl acetate (150 mL)And water (100 mL),Extraction and separation,The aqueous phase was then extracted with ethyl acetate (80 mL)The organic phases were combined,Re-water (80 mL x 2) and saturateWashed with brine (80 mL x 2)Liquid separation,The organic phase was dried over anhydrous sodium sulfate for 3 hours,Filtration and concentration,Crude;The crude product was added petroleum ether (32 mL)And ethyl acetate (6 mL) were stirred for 1 hour,filter,Dried in vacuo to give 4.8 g of 2-chloro-4- (3-pyridyl) pyrimidine,The yield was 74.6%Purity HPLC was greater than 95%.
73%	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; water; for 16h;Heating; Reflux; Inert atmosphere;	Example 11 Preparation of 2-chloro-4-(pyridin-3-yl)pyrimidine[00106] Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen were placed a solution of pyridin-3-ylboronic acid (4.42 g, 36.0 mmol, 1.00 equiv) in THF/H2O (30 mL), a solution of 2,4-dichloropyrimidine (5.40 g, 36.2 mmol, 1.00 equiv) in THF/H2O (30 mL), Na2CO3 (11.5 g, 108 mmol, 3.00 equiv) and PdCl2(PPh3)2 (1.80 g, 2.57 mmol, 0.06 equiv). The resulting solution was heated to reflux for 16 hrs in an oil bath. The reaction mixture was cooled and quenched by the addition of 100 mL of water. The resulting solution was extracted with 5x200 mL of ethyl acetate. The organic layers were combined, washed with 3x200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1: 1). This resulted in 5 g (73%) of 2-chloro-4-(pyridin-3-yl)pyrimidine as a yellow solid.
52%	With bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; for 14h;Reflux; Inert atmosphere;	General procedure: To a solution of 2,4-dichloro-5-methylpyrimidine (500 mg, 3.1 mmol) and 4-trifluoromethoxylphenylboronic acid (644 mg, 3.1 mmol) in dioxane (15 mL), Pd(PPh3)2Cl2 (215 mg, 0.3 mmol) and 2M Na2CO3 (920 mg, 8.7 mmol) were added. The mixture was stirred at reflux for 14 h under N2 atmosphere. The reaction mixture was cooled to room temperature and filtrated. The filtrate was diluted with H2O (100 mL) and then extracted with EtOAc, and the organic layer was dried over anhydrous Na2SO4, After filtration, the filtrate was evaporation and purified by chromatography (petroleum ether/ EtOAc, 5:1) to give the product as oil (700 mg, 73 %).

	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; at 60℃; for 16h;	Step 1.Synthesis of 2-chloro-4-(3-pyridyl)pyrimidine nitrogen was bubbled through a solution of 2,4-dichloropyrimidine (1 eq) in tetrahydrofuran and water (3:1) for 0.5 h. bis(diphenylphosphino)ferrocene Palladium(II)chloride (0.05 eq) followed by pyridine-3-boronic acid (1 eq) and sodium carbonate (3 eq) was added and the mixture was heated to 60 C. for 16 h under nitrogen.The reaction mixture was concentrated and partitioned between ethyl acetate and water.The organic layer was washed with brine and dried with sodium sulfate and concentrated.Purification on silica gel gave 2-chloro-4-(3-pyridyl)pyrimidine. MS: MH+=190.
	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate; In 1,2-dimethoxyethane; water; at 100℃; for 1h;	2-Chloro-4-(pyridin-3-yl)pyrimidine: Pyridin-3-ylboronic acid (263 mg, 2.14 mmol), PEPPSI - IPr (132 mg, 0.195 mmol), and potassium carbonate (2.4 ml of 2 M aqueous solution, 4.8 mmol) were added to 2,4-dichloropyrimidine (290 mg, 1 .95 mmol) in 1 ,2- dimethoxyethane (8 mL) . The reaction mixture was stirred at 100 C for 1 h. The solvents were removed under reduced pressure, and the residue was dissolved in DCM and filtered. The filtrate was purified with silica gel chromatography (20% - 60% EtOAc in hexanes) to yield 150 mg, 40.2 % yield of the title compound. 1H NMR (400 MHz, CHLOROFORM-d) delta 1 H NMR (400 MHz, CHLOROFORM-d) delta 9.28 (br. s., 1 H), 8.79 (d, J = 3.92 Hz, 1 H), 8.73 (d, J = 5.09 Hz, 1 H), 8.46 (d, J = 8.03 Hz, 1 H), 7.72 (d, J = 5.29 Hz, 1 H), 7.49 (dd, 1 H). LCMS: tR = 0.47 min, 93%. MS m/z = 192 (M+H)+.

Reference： [1]Patent: CN106243083,2016,A .Location in patent: Paragraph 0037-0039; 0044-0046; 0051-0053
[2]Patent: WO2011/8788,2011,A1 .Location in patent: Page/Page column 28-29
[3]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 3259 - 3263
[4]Patent: US2004/122237,2004,A1 .Location in patent: Page 179
[5]Patent: WO2013/66839,2013,A2 .Location in patent: Page/Page column 31
[6]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5029 - 5036

3
[ 1692-25-7 ]
[ 33332-28-4 ]
[ 925677-98-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With caesium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 90℃; for 16h;	6-Pyridin-3-ylpyrazin-2-amine An oven dried resealable Schlenk tube was charged with 6-chloropyrazin-2-amine (0.73 g, 5.71 mmol), 3-pyridineboronic acid (0.91 g, 7.42 mmol), dioxane (50 mL) and a 2M aqueous solution of cesium carbonate (8.5 mL, 17.13 mmol). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and 1 ,1'- bis(diphenylphosphino)ferrocene-palladium(ll) dichloride dichloromethane complex (290mg, 0.35 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 9O0C oil bath. After 16h, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. The residue was purified by silica gel flash chromatography (95:5 dichloromethane/methanol) to give the title compound (845 mg, 86percent) as a solid. delta 1H-NMR (CDCI3): 9.18 (s, 1H), 8.67 (d, 1H), 8.38 (s, 1H), 8.25 (m, 1H), 7.99 (s, 1 H), 7.41 (m, 1 H), 4.77 (s, 2H). ESI/MS (m/e, percent): 172 [(M+1)\\ C9H8N4].

Reference： [1]Patent: WO2007/17096,2007,A1 .Location in patent: Page/Page column 51-52

4
[ 1692-25-7 ]
[ 121554-10-7 ]
[ 934470-17-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; at 100℃; for 72h;	Reference Example 11 5-Bromo-2-iodobenzonitrile and 3-pyridylboric acid were dissolved in a mixture solution of aqueous 2 M sodium carbonate solution and toluene, then tetrakis(triphenylphosphine)palladium was added thereto, and the mixture was heated, stirred with heating in an argon atmosphere at 100C for 3 days to obtain 5-bromo-2-pyridin-3-ylbenzonitrile. EI: 258, 260.

Reference： [1]Patent: EP1932832,2008,A1 .Location in patent: Page/Page column 16

5
[ 1692-25-7 ]
[ 19733-56-3 ]

Reference： [1]Organic Process Research and Development,2011,vol. 15,p. 831 - 840

6
[ 3993-78-0 ]
[ 1692-25-7 ]
[ 66521-66-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-ium bromide; palladium diacetate; sodium hydroxide; In water; dimethyl sulfoxide; at 100℃; for 10h;	Pd(OAc)2 (35.00 mg, 0.15 mmol) and 1-(2,6-diisopropylphenyl)-3-(2-oxo-2-(2,4,6-tri-tert-butylphenylamino)ethyl)-1H-imidazol-3-iumbromide (96.00 mg, 0.15 mmol) was dissolved in 10 ml of DMSO : H2O,and 4-chloropyrimidin-2-amine (2.00 g, 15.43 mmol), NaOH (0.93 g, 23.15 mmol),pyridin-3-ylboronic acid (2.28 g, 18.5 mmol) were added. The mixture was heated to 100 oCand stirred for 10h. After cooling, the mixturewas poured into EtOAc (40.0 mL and washed with water (2 ×10.0 mL), brine (2 × 25.0 mL), then dried over MgSO4, evaporation ofthe solvent under reduced pressure provided the crude product, which waspurified by column chromatography (hexane : EtOAc = 1:1) afford product as off white solid 1.92 g, 11.15 mmol) in 72percent yield. 1HNMR (300 MHz, DMSO): delta 9.23(dd, J =1.5 Hz, 1H), 8.68 (dd, J1= 3.0 Hz, J2 = 1.8 Hz,1H), 8.41-8.35 (m, 2H), 7.55-7.50 (m, 1H), 7.20 (d, J1 = 5.1 Hz, 1H), 6.78 (bs, 2H); 13C NMR (75 MHz, CDCl3): delta 163.8, 161.6, 159.4, 151.1, 148.0, 134.1,123.7, 106.0. HRMS(ESI) calcd. for C9H9N4 [M+H]+173.0827, found 173.0825.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6657 - 6661

7
[ 1692-25-7 ]
[ 404844-11-7 ]

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6657 - 6661

8
[ 1196155-38-0 ]
[ 1692-25-7 ]
6-(trifluoromethyl)-[2,3'-bipyridine]-4-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; acetonitrile;	A mixture of <strong>[1196155-38-0]2-chloro-6-(trifluoromethyl)isonicotinonitrile</strong> 1 (125 mg, 0.605 mmol), 3- pyridylboronic acid (90 mg, 0.738 mmol), 2M aq. Na2C03 solution (0.6 mL), and ACN (3 mL) was purged with nitrogen at RT for 3 min. [l, l '-Bis(diphenylphosphino)ferrocene] dichloropalladium(II) complex with DCM (1 : 1) (5 molpercent) was added, and the mixture heated at 100 °C for 4 h. The mixture was concentrated and purified via silica gel chromatography to afford compound 2 (114 mg, 76percent) a as white solid. LCMS Mass: 250 (M++l).

Reference： [1]Patent: WO2016/144703,2016,A1 .Location in patent: Paragraph 00359

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[ 1692-25-7 ]

Abiraterone Acetate Related Intermediates

[ 89878-14-8 ]

3-(Diethylboryl)pyridine

Imatinib Related Intermediates

[ 404844-11-7 ]

4-(Chloromethyl)-N-(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)benzamide

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Organoboron

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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. 1692-25-7 ] {[proInfo.proName]}

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[ 1692-25-7 ] Synthesis Path-Downstream 1~8

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Organoboron

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Pyridines

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