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[ CAS No. 50998-17-9 ] {[proInfo.proName]}

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Chemical Structure| 50998-17-9
Chemical Structure| 50998-17-9
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Product Details of [ 50998-17-9 ]

CAS No. :50998-17-9 MDL No. :MFCD00837757
Formula : C8H5BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :NOYFLUFQGFNMRB-UHFFFAOYSA-N
M.W : 209.04 Pubchem ID :610939
Synonyms :

Calculated chemistry of [ 50998-17-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 47.24
TPSA : 25.78 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.96 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : 2.27
Log Po/w (WLOGP) : 2.39
Log Po/w (MLOGP) : 1.61
Log Po/w (SILICOS-IT) : 2.65
Consensus Log Po/w : 2.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.24
Solubility : 0.121 mg/ml ; 0.000577 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 0.745 mg/ml ; 0.00356 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.19
Solubility : 0.0136 mg/ml ; 0.0000652 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.63

Safety of [ 50998-17-9 ]

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

Application In Synthesis of [ 50998-17-9 ]

* 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 [ 50998-17-9 ]
  • Downstream synthetic route of [ 50998-17-9 ]

[ 50998-17-9 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 50998-17-9 ]
  • [ 6298-37-9 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 11, p. 2809 - 2812
[2] Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737
  • 2
  • [ 50998-17-9 ]
  • [ 7467-91-6 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 11, p. 5351 - 5358
[2] Journal of the American Chemical Society, 2016, vol. 138, # 41, p. 13493 - 13496
[3] Organic Letters, 2017, vol. 19, # 11, p. 3033 - 3036
  • 3
  • [ 50998-17-9 ]
  • [ 97674-02-7 ]
  • [ 83570-42-7 ]
Reference: [1] Patent: US2005/256309, 2005, A1, . Location in patent: Page/Page column 35
[2] Patent: US2005/272736, 2005, A1, . Location in patent: Page/Page column 35
[3] Patent: WO2016/30443, 2016, A1, . Location in patent: Page/Page column 80
[4] Patent: WO2017/144633, 2017, A1, . Location in patent: Page/Page column 95
[5] Patent: WO2017/144639, 2017, A1, . Location in patent: Page/Page column 80
  • 4
  • [ 3476-89-9 ]
  • [ 91-19-0 ]
  • [ 50998-17-9 ]
  • [ 76982-23-5 ]
YieldReaction ConditionsOperation in experiment
35% With bromine In acetonitrile for 2.5 h; Reflux; Inert atmosphere General procedure: Bromine was added dropwise to a magnetically stirred refluxing solution of quinoxaline (1) or tetrahydroquinoxaline 15 or 19 in the relevant solvent. The resulting reaction mixture was heated at reflux temperature. The reaction was monitored by TLC or 1H NMR spectroscopy. After the desired time, the resulting reaction mixture was allowed to cool to room temperature and the solvent was removed under reduced pressure. The mixture was diluted with a saturated solution of sodium carbonate (10mL) and the mixture was extracted with ethyl acetate (2×25mL). Combined organic layers were washed with water, dried over Na2SO4 and concentrated. The crude was purified appropriate method described in below.
Reference: [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632
  • 5
  • [ 34413-35-9 ]
  • [ 50998-17-9 ]
  • [ 76982-23-5 ]
Reference: [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632
[2] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632
  • 6
  • [ 2423-66-7 ]
  • [ 50998-17-9 ]
  • [ 76982-23-5 ]
Reference: [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632
[2] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632
  • 7
  • [ 528852-07-5 ]
  • [ 50998-17-9 ]
  • [ 76982-23-5 ]
Reference: [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632
  • 8
  • [ 91-19-0 ]
  • [ 50998-17-9 ]
  • [ 76982-23-5 ]
Reference: [1] Tetrahedron, 2017, vol. 73, # 12, p. 1618 - 1632
  • 9
  • [ 50998-17-9 ]
  • [ 201230-82-2 ]
  • [ 130345-50-5 ]
Reference: [1] Tetrahedron, 2007, vol. 63, # 27, p. 6252 - 6258
  • 10
  • [ 50998-17-9 ]
  • [ 73183-34-3 ]
  • [ 1167418-13-4 ]
YieldReaction ConditionsOperation in experiment
98% With potassium acetate In 1,4-dioxane at 23 - 90℃; Example 60. 6-Quinoxaline boronic acid, pinacol ester (S50)To 6-bromoquinoxaline (418 mg, 2.00 mmol, 1.00 equiv) in dioxane (10 niL) at 23 0C was added PdCl2(dppf) -CH2Cl2 (163 mg, 0.200 mmol, 0.100 equiv), bis(pinacolato)diborone (610 mg, 2.40 mmol, 1.20 equiv), and KOAc (392 mg, 4.00 mmol, 2.00 equiv). After stirring for 1.5 hr at 900C, the reaction mixture was cooled to 23 0C and concentrated in vacuo. The residue was dissolved in CH2Cl2 and filtered through a plug of Celite. After the removal of CH2Cl2, the residue was purified by chromatography on silica gel eluting with hexanes/EtOAc 4:1 (v/v) to afford 500 mg of the title compound as a colorless solid (98percent yield).R/= 0.45 (hexanes/EtOAc 1:1 (v/v)). NMR Spectroscopy: 1H NMR (500 MHz, CDCl3, 23 0C, δ): 8.86-8.82 (m, 2H), 8.59 (s, IH), 8.12 (dd, /= 8.0 Hz, 2.0 Hz, IH), 8.06 (d, / = 8.0 Hz, IH), 1.37 (s, 12H). 13C NMR (125 MHz, CDCl3, 23 0C, δ): 145.53, 145.03, 144.37, 142.41, 137.31, 134.75, 131.90 (br), 128.44, 84.36, 24.86. Mass Spectrometry: HRMS-FIA (m/z): Calcd for [M + H]+, 257.14558. Found, 257.14440.
Reference: [1] Organic Letters, 2009, vol. 11, # 13, p. 2860 - 2863
[2] Patent: WO2010/59943, 2010, A2, . Location in patent: Page/Page column 86
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4735 - 4751
[4] Journal of the American Chemical Society, 2017, vol. 139, # 24, p. 8267 - 8276
[5] Organic Letters, 2018, vol. 20, # 6, p. 1530 - 1533
[6] Patent: CN105254613, 2016, A, . Location in patent: Paragraph 0095; 0096; 0097
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