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[ CAS No. 63996-36-1 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 63996-36-1
Chemical Structure| 63996-36-1
Chemical Structure| 63996-36-1
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Product Details of [ 63996-36-1 ]

CAS No. :63996-36-1 MDL No. :MFCD04116231
Formula : C11H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :FBQFCXDBCPREBP-UHFFFAOYSA-N
M.W :234.09 Pubchem ID :1515237
Synonyms :

Calculated chemistry of [ 63996-36-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 57.37
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.4
Log Po/w (XLOGP3) : 3.32
Log Po/w (WLOGP) : 3.51
Log Po/w (MLOGP) : 2.82
Log Po/w (SILICOS-IT) : 3.7
Consensus Log Po/w : 3.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.0
Solubility : 0.0234 mg/ml ; 0.0001 mol/l
Class : Moderately soluble
Log S (Ali) : -3.27
Solubility : 0.127 mg/ml ; 0.000541 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.4
Solubility : 0.00093 mg/ml ; 0.00000397 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.71

Safety of [ 63996-36-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 63996-36-1 ]

* 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 [ 63996-36-1 ]
  • Downstream synthetic route of [ 63996-36-1 ]

[ 63996-36-1 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 63996-36-1 ]
  • [ 129013-83-8 ]
Reference: [1] Patent: US5714496, 1998, A,
  • 2
  • [ 110-86-1 ]
  • [ 589-87-7 ]
  • [ 63996-36-1 ]
  • [ 39795-60-3 ]
  • [ 129013-83-8 ]
Reference: [1] Heterocycles, 2004, vol. 64, p. 499 - 504
[2] Tetrahedron, 2006, vol. 62, # 33, p. 7824 - 7837
  • 3
  • [ 110-86-1 ]
  • [ 622-88-8 ]
  • [ 63996-36-1 ]
  • [ 129013-83-8 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 54, p. 7124 - 7127
  • 4
  • [ 63996-36-1 ]
  • [ 383128-14-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 21, p. 5817 - 5820[2] Angew. Chem., 2017, vol. 129, p. 5911 - 5914,4
  • 5
  • [ 63996-36-1 ]
  • [ 897962-21-9 ]
  • [ 94928-86-6 ]
  • [ 501330-36-5 ]
Reference: [1] Chemical Communications, 2008, vol. 8, # 5, p. 618 - 620
  • 6
  • [ 63996-36-1 ]
  • [ 73183-34-3 ]
  • [ 908350-80-1 ]
YieldReaction ConditionsOperation in experiment
82% With potassium acetate; tricyclohexylphosphine In 1,4-dioxane for 20 h; Inert atmosphere; Reflux 1.
Preparation of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)pyridine
0.39 g (0.4 mmol) of Pd(dba)3 and 0.28 g (1 mmol) of tricyclohexylphosphine are suspended in 10 ml of dry dioxane under a nitrogen atmosphere.
The resulting mixture is stirred at room temperature for 30 minutes.
Subsequently, 5.3 g (15 mmol) of bis(pinacolato)diboron, 2.1 g (21 mmol) of KOAc and 3.3 g (14 mmol) of 2-(4-bromophenyl)pyridine are added gradually.
The reaction mixture is boiled under reflux for 20 hours, cooled and treated with 10 ml of water at room temperature.
The product is extracted with dichloromethane.
The solvent is removed under reduced pressure and the resulting crude product is purified by means of a short silica gel column.
After purification by means of the silica gel column (dichloromethane/hexane, 3:1), 82percent of the desired product is obtained.
1H NMR(CDCl3): δ=1.37(s,12H), 7.22-7.26(m, 1H), 7.72-7.80(m, 2H), 7.92(J=8.4 Hz, 2H), 8.02(J=8.2Hz, 2H), 8.71(J=4.9 Hz, 1H).
11.2 g for 2 h; Inert atmosphere; Reflux First, a solution was added cyclopentyl methyl ether (CPME) in (64 ml) 2-(4- bromophenyl) pyridine (15 g) and bis (pinacolato) diboron (19.5 g), under a nitrogen atmosphere, palladium acetate (Pd ( OAc) 2) (0.4g), triphenylphosphine (PPh3) (1.5g) and potassium acetate (AcOK) (18.9g) was added with stirring at room temperature. After stirring for 2 hours at reflux temperature, the reaction mixture was cooled to room temperature, was added with ethylenediaminetetraacetic acid (EDTA) solution (35 ml) in toluene (500ml). The organic matter to remove salts by water washing operation was purified with activated carbon column chromatography (toluene). There was thus obtained 2- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) pyridine (11.2 g).
Reference: [1] Patent: US2013/231489, 2013, A1, . Location in patent: Paragraph 0184; 0185
[2] Patent: JP5673362, 2015, B2, . Location in patent: Paragraph 1082; 1084
  • 7
  • [ 63996-36-1 ]
  • [ 121-43-7 ]
  • [ 170230-27-0 ]
YieldReaction ConditionsOperation in experiment
65.8%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 16 h; Inert atmosphere
(2) Weigh 5.0 g (21.36 mmol) of compound 1 in a three-30 mL of anhydrous tetrahydrofuran (THF) was added by a syringe under a nitrogen atmosphere,The temperature of the system was lowered to -78 ° C using an acetone / liquid nitrogen bath,11.2 mL (2.5 M) of n-BuLi (n-BuLi) solution was slowly added dropwise with a syringe,The reaction was stirred at -78 ° C for 1 hour.Under nitrogen atmosphere, 7.4 mL (64.08 mmol)(B (OMe) 3),Remove the acetone / liquid nitrogen bath,The reaction was stirred at room temperature for 16 hours.Water quenching reaction,The mixture was extracted with dichloromethane (CH2Cl2)The organic phase was dried over anhydrous sodium sulfate (Na2SO4) and concentrated.With petroleum ether precipitation, a white solid precipitation,The filter cake was filtered and vacuum dried,To give 2.80 g (yield 65.8percent) of a white solid,By NMR characterization,The product was the target product 2:
Reference: [1] Chemistry of Materials, 2016, vol. 28, # 23, p. 8556 - 8569
[2] Patent: CN105859793, 2016, A, . Location in patent: Paragraph 0029; 0030; 0032
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