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[ CAS No. 408492-27-3 ] {[proInfo.proName]}

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Chemical Structure| 408492-27-3
Chemical Structure| 408492-27-3
Structure of 408492-27-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 408492-27-3 ]

CAS No. :408492-27-3 MDL No. :MFCD09746195
Formula : C11H14BCl2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :PEFDHAOFDBNZEQ-UHFFFAOYSA-N
M.W : 273.95 Pubchem ID :44516386
Synonyms :

Calculated chemistry of [ 408492-27-3 ]

Physicochemical Properties

Num. heavy atoms : 17
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 : 70.73
TPSA : 31.35 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 3.76
Log Po/w (WLOGP) : 2.69
Log Po/w (MLOGP) : 1.67
Log Po/w (SILICOS-IT) : 2.58
Consensus Log Po/w : 2.14

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.1
Solubility : 0.0216 mg/ml ; 0.000079 mol/l
Class : Moderately soluble
Log S (Ali) : -4.11
Solubility : 0.0212 mg/ml ; 0.0000774 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.86
Solubility : 0.00383 mg/ml ; 0.000014 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.75

Safety of [ 408492-27-3 ]

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 [ 408492-27-3 ]

* 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 [ 408492-27-3 ]
  • Downstream synthetic route of [ 408492-27-3 ]

[ 408492-27-3 ] Synthesis Path-Upstream   1~10

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Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 49, p. 17197 - 17202
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Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 49, p. 17197 - 17202
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Reference: [1] Journal of the American Chemical Society, 2018, vol. 140, # 49, p. 17197 - 17202
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Reference: [1] Journal of the American Chemical Society, 2003, vol. 125, # 26, p. 7792 - 7793
[2] Synthesis, 2011, # 6, p. 857 - 859
  • 5
  • [ 557-21-1 ]
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Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 33, p. 11389 - 11391
  • 6
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  • [ 73183-34-3 ]
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YieldReaction ConditionsOperation in experiment
88% at 100℃; for 1 h; Inert atmosphere Intermediate 24:-dichloro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridineUnder an atmosphere of nitrogen, a mixture of 2,6-dichloropyridine (3g, 20.3mmol), 4,4,4,,4,,5,5,5,,5'-octamethyl-2,2,-bi-1 ,3,2-dioxaborolane (5.92g, 23.3mmol), 1 ,10- phenanthroline (145mg, 0.81 mmol) and chlorobis(1 ,5-cyclooctadiene)iridium(l) dimer (267mg, 0.30mmol) was treated with 1 ,2-dichloroethane (20ml_). Nitrogen was passed through the mixture for 5 minutes after which time the mixture was heated at 100°C for 1 hour. The cooled reaction mixture was poured into a mixture of diethyl ether (150ml_) and aqueous sodium hydroxide solution (4M, 200ml_) and the phases were separated. The aqueous phase was ice-cooled and acidified with aqueous hydrochloric acid (5M) and the resulting precipitate was filtered, washed with water and dried to afford the title compound (4.9g, 17.9mmol, 88percent yield). LCMS (Method A): Rt 0.74 minutes; m/z 192,194 (ionised as the boronic acid) (MH+). NMR (400MHz, dmso-d6) δ 1.28 (12H, s), 7.57 (2H, s).
58% With 1,10-Phenanthroline In 1,2-dichloro-ethane at 100℃; for 15 h; To a mixture of 2, 6-dichloropyridine (3.28 g, 22.2 mmol) and bis (pinacolato) diboron (6.2 g, 24.4 mmol) was added 1,10-phenanthroline (0.24 g, 1.3 mmol) and CHLORO-1, 5-cyclooctadiene iridium (I) dimer (0.44 g, 0.66 mmol) under nitrogen followed by anhydrous 1,2- dichloroethane. Nitrogen was bubbled through the mixture for 5 minutes and the reaction was then heated with stirring at 100 °C for 15 hours under an atmosphere of nitrogen. The mixture was allowed to cool to room temperature, poured onto DIETHYLETHER/4N sodium hydroxide (50 ml/200 ml) and the phases separated. The aqueous phase was acidified with 6N hydrochloric acid and the resulting solid was filtered, washed with water and dried on the sinter to yield the pinacol ester of 2, 6-dichloropyridin-4-ylboronic acid (3.5 g, 58 percent) as a grey solid.
58% With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine In tetrahydrofuran at 80℃; for 19 h; Inert atmosphere; Glovebox Example 4
Borylation of Pyridines
Borylation of 2,6-Dichloropyridine
An oven-dried 3 mL screw-cap Wheaton® vial was charged inside a nitrogen-filled glovebox with [Ir(OMe)cod]2 (3.3 mg, 0.005 mmol) and dtbpy (2.7 mg, 0.01 mmol). THF (1.5 mL) was added, followed by B2pin2 (127 mg, 0.5 mmol) and 2,6-dichloropyridine (147 mg, 1.0 mmol). The vial was capped and heated outside of the glovebox at 80° C. for 19 h. The reaction solvent was removed on a rotary evaporator, and the residue was purified by flash column chromatography using hexanes-EtOAc mixtures as eluent providing 2,6-dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine as a white solid (160 mg, 58percent): 1H NMR (300 MHz, CDCl3) δ 7.57 (s, 1H), 1.33 (s, 12H)
4.8 g With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,10-Phenanthroline In 1,2-dichloro-ethane at 100℃; for 15 h; Inert atmosphere; Sealed tube 2,6-Dichloropyridine (20.3 mmol, 3.0 g), bis-(pinacolato)diboron (22.3 mmol, 5.66 g) and 1,10-phenantroline (1.2 mmol, 0.212 g) were dissolved in dry 1,2- dichloroethane (100 ml) , degassed and purged with Ar for 5 minutes. Chloro-1,5- cyclooctadiene iridium(I) dimer (0.445 g, 0.7 mmol) was added and the resulting reaction mixture was stirred at 100°C for 15 hours in sealed tube conditions. Aftercompletion of the reaction the contents were cooled, filtered through Celite and 1,2- dichloroethane was evaporated with vacuum. The crude residue was dissolved in diethyl ether and washed with sodium hydroxide (4N solution in water). The aqueous layer was acidified to pH=1 with HC1 (6N solution in water) and resulting solid was filtered off and washed with water. 4.8 g of the title compound was obtained as a grey solid.

Reference: [1] Organic Letters, 2009, vol. 11, # 16, p. 3586 - 3589
[2] Journal of the American Chemical Society, 2015, vol. 137, # 25, p. 8058 - 8061
[3] Organic and Biomolecular Chemistry, 2014, vol. 12, # 37, p. 7318 - 7327
[4] Patent: WO2011/110575, 2011, A1, . Location in patent: Page/Page column 73
[5] Journal of the American Chemical Society, 2018, vol. 140, # 49, p. 17197 - 17202
[6] Advanced Synthesis and Catalysis, 2010, vol. 352, # 10, p. 1662 - 1666
[7] Patent: WO2004/46133, 2004, A1, . Location in patent: Page 34
[8] Patent: US2015/65743, 2015, A1, . Location in patent: Paragraph 0370; 0371
[9] Synlett, 2009, # 1, p. 147 - 150
[10] Tetrahedron Letters, 2009, vol. 50, # 45, p. 6176 - 6179
[11] Journal of the American Chemical Society, 2010, vol. 132, # 33, p. 11389 - 11391
[12] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6622 - 6625
[13] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 10, p. 3001 - 3006
[14] Patent: WO2014/128223, 2014, A1, . Location in patent: Page/Page column 14; 15
[15] Organometallics, 2017, vol. 36, # 17, p. 3429 - 3434
[16] Patent: US2018/51042, 2018, A1, . Location in patent: Paragraph 0052
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YieldReaction ConditionsOperation in experiment
67% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In N,N-dimethyl-formamide at 90℃; for 3 h; Inert atmosphere Example 18.N-(3-fluoro-6’-(5-( 1-methyl-i H-pyrazol-4-yl)-1H-bzd[d}iniidazo1 i-yl)-[2,4’-bipyridinj-2-yl)cyclopropaiiesulfonamide. .a) 2,6-Dichloro-4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)pyridine. A solution of 2,6-dichloro-4-iodopyridine (15 g, 54.9 mmol) in DMF (150 ml)was degassed by N2 bubbling for 5 mm. Bispinacolato diborane (17.63 g, 82.4 mrnol,1.5 eq) was added and the mixture was degassed for another 5 mm. Pd(dppf)C12 (2.24 g,2.7 mmol, 0.05 eq) and potassium acetate (8.07 g, 82.4 mmol, 1.5 eq) were addedsequentially using the procedure of Intermediate Example 1 and the mixture was then heated at 90 °C for 3 h. The reaction mixture was then quenched and extracted as in Intermediate Example 1. The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica gel, 50 percent ethyl acetate in hexane) to afford the title product in 67 percent yield (10 g). 1H NMR (300 MHz, CDCl3)o7.59 (s5 2H), 1.35 (s, 611), 1.26 (s, 6H).
Reference: [1] Patent: WO2014/162039, 2014, A1, . Location in patent: Page/Page column 54; 55
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YieldReaction ConditionsOperation in experiment
58% at 100℃; for 15 h; Description 6 2*6-DICHLORO-4-(3-METHVL-2-PYRIDYL) PERIDINE To a mixture of 2, 6-dichloropyridine (3.28 g, 22.2 mmol) and bis (PINACOLATO) diboron (6.2 g, 24.4 mmol) was added 1, 10-phenanthroline (0.24 g, 1. 3 mmol) and CHLORO-1, 5-CYCLOOCTADIENE iridium (I) dimer (0.44 g, 0.66 mmol) under nitrogen followed by anhydrous 1, 2-dichloroethane. Nitrogen was bubbled through the mixture for 5 min and the reaction was then heated with stirring at 100 C for 15 h under an atmosphere of nitrogen. The mixture was allowed to cool to room temperature, poured onto DIETHYLETHER/4N sodium hydroxide (50 ML/200 ML) and the phases separated. The aqueous phase was acidified with 6N hydrochloric acid and the resulting solid was filtered, washed with water and dried on the sinter to yield pinacol 2,6-dichloropyridine-4-boronate (3.5 g, 58 percent) as a grey solid, MS: (ES (M+1)) 274/276. LH NMR (360 MHz, DMSO) 8 1.30 (12H, s), 7.57 (2H, s) ppm
Reference: [1] Patent: WO2004/74290, 2004, A1, . Location in patent: Page 38
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Reference: [1] Dalton Transactions, 2015, vol. 44, # 29, p. 13007 - 13016
[2] Journal of Organic Chemistry, 2015, vol. 80, # 16, p. 8341 - 8353
[3] Journal of the American Chemical Society, 2003, vol. 125, # 26, p. 7792 - 7793
[4] Advanced Synthesis and Catalysis, 2004, vol. 346, # 13-15, p. 1655 - 1660
[5] Patent: US2004/30197, 2004, A1, . Location in patent: Page 14; 17
[6] Synthesis, 2011, # 6, p. 857 - 859
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YieldReaction ConditionsOperation in experiment
71% at 80 - 90℃; The reaction liquid was cooled to 0 ° C, filtered, and the solvent was evaporated to dryness, and then sulfolane was added, and the intermediate was rectified to obtain 2,6-dichloropyridine-4-(ditetrahydropyrrolyl)borate in a yield of 78percent.After heating and melting the pinacol (18.4 g, 0.16 mol), the temperature was 80-90 ° C, and the mixture was dropped into the above intermediate.During the dropwise addition, the tetrahydropyrrole formed was separated and completely exchanged. After cooling, the ethanol and n-heptane mixed solvent were beaten to obtain 38.9 g of a pale yellow solid, and the yield was 71percent.
Reference: [1] Patent: CN107987097, 2018, A, . Location in patent: Paragraph 0016; 0019; 0023; 0027
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