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[ CAS No. 381233-75-6 ] {[proInfo.proName]}

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Chemical Structure| 381233-75-6
Chemical Structure| 381233-75-6
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Product Details of [ 381233-75-6 ]

CAS No. :381233-75-6 MDL No. :MFCD08688586
Formula : C5H3BrINO Boiling Point : -
Linear Structure Formula :- InChI Key :WAUPPDAXWKLNNU-UHFFFAOYSA-N
M.W : 299.89 Pubchem ID :12027787
Synonyms :

Calculated chemistry of [ 381233-75-6 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.48
TPSA : 32.86 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) : -7.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.66
Log Po/w (XLOGP3) : 1.28
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 1.97
Log Po/w (SILICOS-IT) : 3.22
Consensus Log Po/w : 1.97

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.0
Solubility : 0.301 mg/ml ; 0.001 mol/l
Class : Soluble
Log S (Ali) : -1.57
Solubility : 8.08 mg/ml ; 0.0269 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.72
Solubility : 0.0567 mg/ml ; 0.000189 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.14

Safety of [ 381233-75-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 381233-75-6 ]

* 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 [ 381233-75-6 ]
  • Downstream synthetic route of [ 381233-75-6 ]

[ 381233-75-6 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 13466-38-1 ]
  • [ 381233-75-6 ]
YieldReaction ConditionsOperation in experiment
92.6% With N-iodo-succinimide In acetonitrile at 82℃; for 0.333333 h; Will contain 5-bromo-2-hydroxypyridine (2.5 g, 14.4 mmol), A mixture of iodosuccinimide (4.7 g, 20.9 mmol) and acetonitrile (40 mL) was stirred at 82 ° C for 20 min. After cooling to room temperature, filtration, the cake was recrystallized from ethyl acetate to give 5-bromo-2-hydroxy-3-iodopyridine (65) (4.0 g). The yield was 92.6percent.
83% With N-iodo-succinimide In acetonitrile for 4 h; Reflux To 5-bromo-2-hydroxypyridine I (5g, 29mmol) was added solid N Jodosuccinimide (7.lg, 32mmol) in acetonitrile (l2OmL). The solution was stirred at reflux for 4 hours and followed by TLC. The solution was cooled to room temperature, filteredand washed with methanol. 5-bromo-2-hydroxy-3-.iodopyridine 2 was obtained as a pink solid (yield: 83percent).
33% With N-iodo-succinimide In N,N-dimethyl-formamide at 50℃; for 6 h; Synthesis of 5-bromo-3-iodopyridin-2-ol (218): 5-Bromopyridin-2-ol (1.74 g, 10 mmol) was dissolved in DMF (40 mL) and NIS (2.7 g, 12 mmol) was added at room temperature. The reaction mixture was heated at 50 °C for 6 h. The reaction mixture was cooled down to room temperature, poured into 50 mL of water, extracted with EtOAc (60 mL X 3). The combined organic layers were washed with brine, dried over anhydrous Na2S04, and concentrated under reduced pressure to give 5-bromo-3-iodopyridin-2-ol (218) as yellow solid (1.0 g, 33percent yield). LCMS: m/z 301.9 [M+H]+; tR = 1.34 min.
Reference: [1] Patent: CN108084186, 2018, A, . Location in patent: Paragraph 0187-0188
[2] Synlett, 2003, # 11, p. 1678 - 1682
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 4, p. 1644 - 1668
[4] Patent: WO2015/132727, 2015, A1, . Location in patent: Page/Page column 22; 28
[5] Heterocycles, 2002, vol. 57, # 1, p. 55 - 71
[6] Patent: WO2015/3166, 2015, A1, . Location in patent: Paragraph 00691
  • 2
  • [ 13466-38-1 ]
  • [ 381233-75-6 ]
YieldReaction ConditionsOperation in experiment
86% With N-iodo-succinimide In toluene at 90℃; for 0.333333 h; Inert atmosphere To a solution of 5-bromo-2-(1H)-pyridone (18.8 gf 10.8 mmol) in dry toluene {400 ml_) was added N-iodosuccinimide (24.3 g, 10.8 mmol) under nitrogen. The reaction mixture was stirred at 90 °C for 20 minutes then cooled to 25 °C. The precipitate was filtered off and washed with methanol, dried under vacuum to give the pink-orange color solid 28.0 g (86percent). 1H NMR (300 MHz, CDCi3 ) δ 8.1 (s, 1 H), 7.6 (s, 1 H). Mass caicuiated for formula C5H3BrINO 298.84, observe MS ES+: 300.0/302.0.
Reference: [1] Patent: WO2010/118207, 2010, A1, . Location in patent: Page/Page column 282-283
  • 3
  • [ 1072-97-5 ]
  • [ 381233-75-6 ]
Reference: [1] Heterocycles, 2002, vol. 57, # 1, p. 55 - 71
  • 4
  • [ 381233-75-6 ]
  • [ 928653-73-0 ]
YieldReaction ConditionsOperation in experiment
82% at 160℃; for 4 h; 2 (9g, 3Ommol) was dissolved in phenyiphosphonic dichloride 90percent (l0OmL,0.3mol). The mixture was stirred and heated (160°C) for 4 hours and followed by TLC. At room temperature, it was introduced drops in a vial of 1 L filled with water and cooled at 0°C. The solution was neutralized by addition of NH4OH solution. The mixture wasextracted in ethyl acetate. The product was obtained as a white solid, 5-bromo-2-chloro-3- iodopyridine 3 (yield: 82percent),
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 4, p. 1644 - 1668
[2] Patent: WO2015/132727, 2015, A1, . Location in patent: Page/Page column 22; 23; 28
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