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[ CAS No. 100397-96-4 ] {[proInfo.proName]}

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Chemical Structure| 100397-96-4
Chemical Structure| 100397-96-4
Structure of 100397-96-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 100397-96-4 ]

CAS No. :100397-96-4 MDL No. :MFCD04114399
Formula : C13H10BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :NKFPGRBMSCKIBN-UHFFFAOYSA-N
M.W : 276.13 Pubchem ID :21847953
Synonyms :

Calculated chemistry of [ 100397-96-4 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 66.62
TPSA : 29.96 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) : -5.98 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.17
Log Po/w (XLOGP3) : 2.82
Log Po/w (WLOGP) : 3.27
Log Po/w (MLOGP) : 2.34
Log Po/w (SILICOS-IT) : 3.88
Consensus Log Po/w : 2.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.69
Solubility : 0.057 mg/ml ; 0.000206 mol/l
Class : Soluble
Log S (Ali) : -3.11
Solubility : 0.216 mg/ml ; 0.000782 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.75
Solubility : 0.000496 mg/ml ; 0.00000179 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.57

Safety of [ 100397-96-4 ]

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 [ 100397-96-4 ]

* 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 [ 100397-96-4 ]
  • Downstream synthetic route of [ 100397-96-4 ]

[ 100397-96-4 ] Synthesis Path-Upstream   1~5

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YieldReaction ConditionsOperation in experiment
92%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at 0℃; for 0.5 h; Inert atmosphere
Stage #2: at -65℃; for 1.25 h; Inert atmosphere
To a solution of LDA (51 ml, 2M in THF) in THF (50 mL), was slowly added 4-methylpyridine (9.5 g, 102 mmol) at 0° C. under N2.
After 30 minutes the resulting anion was cooled to -65° C.
In a separate round bottom flask, 4-bromo-N-methoxy-N-methylbenzamide was dissolved in THF (50 ml) and cooled to -65° C. under N2.
To this, a freshly prepared anion (1.2 eq) solution was slowly added over a period of 45 minutes.
After an additional 30 minutes, AcOH (50 ml) was slowly added and the reaction was allowed to warm up to room temperature.
The mixture was basified to pH7 and extracted with EA.
The organic extract was washed with brine, dried over Na2SO4, filtered and concentrated.
The residue was recrystallized from (PE:EA=10:1) to give the titled product as a yellow solid (5.2 g, yield: 92percent); MS (ESI) m/z=276 [M+H]+.
Reference: [1] Patent: US2013/158031, 2013, A1, . Location in patent: Paragraph 0180; 0181
[2] MedChemComm, 2013, vol. 4, # 2, p. 443 - 449
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YieldReaction ConditionsOperation in experiment
72.4%
Stage #1: With n-butyllithium In tetrahydrofuran at -78 - 22℃; for 20.5 h;
I. Preparation Examples PRECURSOR 1: 4-(3-(4-bromophenyl)-1-methyl-1H-pyrazol-4-yl)pyridine 1) (1-(4-bromophenyl)-2-(pyridin-4-yl)ethanone 4-Methylpyridine (10.9 g, 117 mmol) was dissolved in THF (150 ml) and cooled to -78° C. with stirring.
Butyllithium (40 ml, 100 mmol) was added slowly to the solution.
The resulting solution was stirred at -78° C. for 30 min.
A solution of 4-bromobenzonitrile (21.84 g, 120 mmol) in THF (150 ml) was added slowly and the reaction mixture was stirred for 2 h at -78° C.
The resulting solution was allowed to warm and it was stirred at 22° C. for 18 h.
Water was added, and then acidified with 48percent hydrobromic acid.
The solvent was removed on the rotary evaporator and the resulting acidic aqueous solution was refluxed for 2 h.
The cooled aqueous solution was extracted several times with diethyl ether, and upon neutralization of the acidic aqueous layer.
The 4-phenacylpyridine precipitated as a yellow solid (1-(4-bromophenyl)-2-(pyridin-4-yl)ethanone (20 g, 72.4 mmol, 72.4percent yield)). LC-MS (Method B): m/z 278 (M+H), RT: 1.86 min.
Reference: [1] Patent: US2014/148461, 2014, A1, . Location in patent: Paragraph 0334-0335
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Reference: [1] MedChemComm, 2013, vol. 4, # 2, p. 443 - 449
[2] Patent: US2013/158031, 2013, A1,
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Reference: [1] Justus Liebigs Annalen der Chemie, 1956, vol. 600, p. 176,188
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Reference: [1] Justus Liebigs Annalen der Chemie, 1956, vol. 600, p. 176,188
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