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[ CAS No. 329214-79-1 ] {[proInfo.proName]}

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Chemical Structure| 329214-79-1
Chemical Structure| 329214-79-1
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Product Details of [ 329214-79-1 ]

CAS No. :329214-79-1 MDL No. :MFCD03084758
Formula : C11H16BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XEMDFESAXKSEGI-UHFFFAOYSA-N
M.W : 205.06 Pubchem ID :2734656
Synonyms :

Calculated chemistry of [ 329214-79-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.55
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 60.71
TPSA : 31.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.84
Log Po/w (WLOGP) : 1.38
Log Po/w (MLOGP) : 0.58
Log Po/w (SILICOS-IT) : 1.31
Consensus Log Po/w : 1.02

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.5
Solubility : 0.648 mg/ml ; 0.00316 mol/l
Class : Soluble
Log S (Ali) : -2.12
Solubility : 1.56 mg/ml ; 0.0076 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.63
Solubility : 0.0481 mg/ml ; 0.000234 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.84

Safety of [ 329214-79-1 ]

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:

Application In Synthesis of [ 329214-79-1 ]

* 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 [ 329214-79-1 ]
  • Downstream synthetic route of [ 329214-79-1 ]

[ 329214-79-1 ] Synthesis Path-Upstream   1~19

  • 1
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  • [ 73183-34-3 ]
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Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4287 - 4299
[2] Tetrahedron Letters, 2002, vol. 43, # 32, p. 5649 - 5651
  • 2
  • [ 108-36-1 ]
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  • [ 4422-32-6 ]
Reference: [1] Chemical Communications, 2008, # 7, p. 889 - 890
[2] Patent: US2009/289547, 2009, A1, . Location in patent: Page/Page column 47
[3] Patent: US2011/155955, 2011, A1, . Location in patent: Page/Page column 7-8
  • 3
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YieldReaction ConditionsOperation in experiment
49% With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; potassium acetate In 1,4-dioxane at 60℃; for 10 h; Inert atmosphere; Sealed tube General procedure: In a nitrogen-filled glove box, Silica-3p-TPP ([P] 0.11 mmol/g, 45.5 mg, 0.005 mmol P, 1 mol percent P), anhydrous, degassed benzene (0.8 mL), and a solution of [PdCl(η3-cinnamyl)]2 (0.65 mg, 0.00125 mmol, 0.5 mol percent Pd) in benzene (0.2 mL) were placed in an oven-dried, 10-mL glass tube containing a magnetic stirring bar. After stirring of the mixture for 5 min, KOAc (147 mg, 1.5 mmol), bis(pinacolato)diboron (2, 140 mg, 0.55 mmol), and p-chlorotoluene (1a, 63.3 mg, 0.50 mmol) were added. The tube was sealed with a screw cap and was removed from the glove box. The mixture was stirred at 25 °C for 10 h, and was filtered through a Celite pad (eluting with Et2O). Solvent was removed under reduced pressure. An internal standard (1,1,2,2-tetrachloroethane) was added to a residue to determine the yield of the product by 1H NMR (95percent). The crude material was then purified by silica gel chromatography to give arylboronate 3a (87.0 mg, 0.40 mmol, 80percent yield).
41% With N-ethyl-N,N-diisopropylamine; triphenylphosphine In methanol at 20 - 50℃; Inert atmosphere Under a nitrogen atmosphere, a reaction vessel of 20 ml in volume was charged with bis(pinacolate)diboron (1.34 g (5.3 mmol)), degassed methanol (7.2 g) and diisopropylethylamine (1.36 g (10.6 mmol)) and stirred at room temperature. The reaction vessel was charged with bis(l,5-cyclooctadiene)nickel (39 mg (0.14 mmol)), triphenylphosphine (74 mg (0.28 mmol)), and 3-chloropyridine (0.40 g (3.52 mmol)) and stirred at 300C for 21 hours, and thereafter stirred at500C for 3 hours. The reaction solution was analyzed by gas chromatography. As a result, 3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)pyridine was contained in an amount of 0.29 g (1.42 mmol, yield: 41percent).
41% With N-ethyl-N,N-diisopropylamine; triphenylphosphine In methanol at 20 - 50℃; for 24 h; Inert atmosphere Under a nitrogen atmosphere, a reaction vessel of 20 ml in volume was charged with bis(pinacolate)diboron (1.34 g (5.3 mmol)), degassed methanol (7.2 g) and diisopropylethylamine (1.36 g (10.6 mmol)) and stirred at room temperature. The reaction vessel was charged with bis(1,5-cyclooctadiene)nickel (39 mg (0.14 mmol)), triphenylphosphine (74 mg (0.28 mmol)), and 3-chloropyridine (0.40 g (3.52 mmol)) and stirred at 30° C. for 21 hours, and thereafter stirred at 50° C. for 3 hours. The reaction solution was analyzed by gas chromatography. As a result, 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine was contained in an amount of 0.29 g (1.42 mmol, yield: 41percent).
Reference: [1] ChemCatChem, 2014, vol. 6, # 5, p. 1340 - 1348
[2] RSC Advances, 2018, vol. 8, # 25, p. 13643 - 13648
[3] Angewandte Chemie - International Edition, 2007, vol. 46, # 28, p. 5359 - 5363
[4] Chemistry Letters, 2014, vol. 43, # 5, p. 584 - 586
[5] Patent: WO2010/110782, 2010, A1, . Location in patent: Page/Page column 46-47
[6] Patent: US2012/123122, 2012, A1, . Location in patent: Page/Page column 13
[7] ACS Catalysis, 2018, vol. 8, # 5, p. 4049 - 4054
[8] Tetrahedron, 2001, vol. 57, # 49, p. 9813 - 9816
[9] Organic and Biomolecular Chemistry, 2015, vol. 13, # 11, p. 3236 - 3242
  • 4
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YieldReaction ConditionsOperation in experiment
85.9% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran at 80℃; for 5 h; Inert atmosphere (1) In a 250 mL three-necked flask, nitrogen was introduced,Add 0.02 mol of 3-bromopyridine to the solution100 ml of tetrahydrofuran (THF)Then 0.024 mol bis (pinacolato) diboron,0.0002 mol of (1,1'-bis (diphenylphosphino) ferrocene) dichloropalladium (II) and0.05 mol of potassium acetate was added,The mixture was stirred,The mixed solution of the above reactants was heated under reflux at a reaction temperature of 80 ° C for 5 hours;After the reaction,Cool and add 100 ml of water, and the mixture was filtered and dried in a vacuum oven.The obtained residue was separated and purified on a silica gel column,To obtain 3-pyridine boronic acid pinacol ester;HPLC purity 99.8percent, yield 85.9percent.
35% With meso-tetra(p-tolyl)porphinato-palladium(II); potassium acetate In 1,4-dioxane at 110℃; for 12 h; General procedure: Aryl/heteroaryl bromide 1 (1 mmol), B2pin2(2), B2npg2(4) orBpin (6, 1.2 mmol), and dioxane (5 mL) are taken into a 25 mLround-bottomed flask. KOAc (2 mmol) was added and stirredthe resultant mixture at room temperature for 5 min, PdII-TpTP(0.15 molpercent) was added, and the contents were refluxed on preheatedoil bath at 110 °C under constant stirring in open-air.The reaction progress was ensured by TLC. After completion ofthe reaction, the mixture was cooled, dilute with water (20 mL)and extracted with tertbutylmethyl ether (3 × 10 mL). The combinedn-hexane layers were concentrated, and the crudeproduct obtained was purified by column chromatography (CC)on silica gel using a mixture of ethyl acetate and hexane (1:30)as eluent.
Reference: [1] ChemCatChem, 2014, vol. 6, # 5, p. 1340 - 1348
[2] Patent: CN106946852, 2017, A, . Location in patent: Paragraph 0055; 0056; 0057; 0058
[3] Inorganic Chemistry, 2016, vol. 55, # 17, p. 8871 - 8880
[4] ACS Catalysis, 2018, vol. 8, # 5, p. 4049 - 4054
[5] Synlett, 2018, vol. 29, # 8, p. 1055 - 1060
[6] European Journal of Organic Chemistry, 2012, # 3, p. 595 - 603
[7] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 897 - 901
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 12, p. 5053 - 5074
[9] Organic and Biomolecular Chemistry, 2016, vol. 14, # 42, p. 10090 - 10094
[10] Journal of the American Chemical Society, 2018, vol. 140, # 27, p. 8429 - 8433
  • 5
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Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5394 - 5397
[2] Organic Syntheses, 2005, vol. 81, p. 89 - 97
  • 6
  • [ 626-55-1 ]
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Reference: [1] Chemical Science, 2015, vol. 6, # 5, p. 2943 - 2951
  • 7
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  • [ 76-09-5 ]
  • [ 121-43-7 ]
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Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 35, p. 10396 - 10400[2] Angew. Chem., 2016, vol. 128, # 35, p. 10552 - 10556,5
  • 8
  • [ 462-08-8 ]
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Reference: [1] Journal of Organic Chemistry, 2013, vol. 78, # 5, p. 1923 - 1933
  • 9
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  • [ 73183-34-3 ]
  • [ 181219-01-2 ]
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Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 11, p. 4287 - 4299
[2] Tetrahedron Letters, 2002, vol. 43, # 32, p. 5649 - 5651
  • 10
  • [ 372-47-4 ]
  • [ 25015-63-8 ]
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Reference: [1] Organic Letters, 2018,
  • 11
  • [ 1120-90-7 ]
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Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 607 - 610
  • 12
  • [ 59-67-6 ]
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Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 22, p. 7440 - 7443
[2] Organic Letters, 2017, vol. 19, # 16, p. 4291 - 4294
  • 13
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Reference: [1] Organic Letters, 2017, vol. 19, # 16, p. 4291 - 4294
  • 14
  • [ 76-09-5 ]
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Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 30, p. 11438 - 11441
  • 15
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Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 975 - 984
  • 16
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Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 22, p. 7440 - 7443
  • 17
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Reference: [1] Journal of Organometallic Chemistry, 2006, vol. 691, # 6, p. 1301 - 1306
  • 18
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Reference: [1] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 975 - 984
  • 19
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  • [ 939430-30-5 ]
Reference: [1] Patent: US2011/155955, 2011, A1,
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