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[ CAS No. 1289131-55-0 ] {[proInfo.proName]}

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Chemical Structure| 1289131-55-0
Chemical Structure| 1289131-55-0
Structure of 1289131-55-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1289131-55-0 ]

CAS No. :1289131-55-0 MDL No. :MFCD22576266
Formula : C8H10BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VDYQLUMBDMESTQ-UHFFFAOYSA-N
M.W : 232.08 Pubchem ID :71303271
Synonyms :

Calculated chemistry of [ 1289131-55-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.13
TPSA : 31.35 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) : -6.51 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.29
Log Po/w (XLOGP3) : 1.7
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 1.08
Log Po/w (SILICOS-IT) : 2.19
Consensus Log Po/w : 1.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.46
Solubility : 0.812 mg/ml ; 0.0035 mol/l
Class : Soluble
Log S (Ali) : -1.97
Solubility : 2.47 mg/ml ; 0.0106 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.56
Solubility : 0.0636 mg/ml ; 0.000274 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.28

Safety of [ 1289131-55-0 ]

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 [ 1289131-55-0 ]

* 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 [ 1289131-55-0 ]
  • Downstream synthetic route of [ 1289131-55-0 ]

[ 1289131-55-0 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 73583-37-6 ]
  • [ 109-86-4 ]
  • [ 1289131-55-0 ]
YieldReaction ConditionsOperation in experiment
26%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.25 h; Inert atmosphere
Stage #2: at 20℃; Inert atmosphere
2-Methoxyethanol (0.820 mL, 10.39 mmol) was dissolved in THF (30 mL) and sodium hydride (60percent w/w) (0.416 g, 10.39 mmol) was added under nitrogen and left to stir at rt for 15 min. 4-bromo-2- chloropyridine (0.577 mL, 5.20 mmol) was added and the reaction was left stirring at rt overnight. More 2-methoxyethanol (0.410 mL, 5.19 mmol) was dissolved in 1 ,2-DME (10 mL) and sodium hydride (60percent w/w) (0.208 mg, 5.19 mmol) was added. The mixture was stirred under nitrogen at rt for 15 min then added to the reaction which was stirred at rt for 3 days. Water was added (40 mL) and the organic product was extracted with EtOAc and washed with brine, dried through a hydrophobic frit and concentrated in vacuo. The residue was purified by silica gel column chromatography [0-20percent EtOAc in cyclohexane] and fractions containing product were concentrated in vacuo to give the title compound as a colourless liquid (314 mg, 1.353 mmol, 26.0 percent yield). LCMS (2 min, Formic Acid): Rt = 0.93 min, MH+ = 232/234.
26%
Stage #1: With sodium hydride In tetrahydrofuran at 20℃; Inert atmosphere
Stage #2: at 20℃;
2-Methoxyethanol (0.820 mL, 10.39 mmol) was dissolved in THF (30 mL) and sodium hydride (60 percent w/w) (0.416 g, 10.39 mmol) was added under nitrogen and left to stir at rt for 15 min. 4-bromo-2- chloropyridine (0.577 mL, 5.20 mmol) was added and the reaction was left stirring at rt overnight. Further 2-methoxyethanol (0.410 mL, 5.19 mmol) was dissolved in 1 ,2-DME (10 mL) and sodium hydride (60 percent w/w) (0.208 mg, 5.19 mmol) was added. After 15 min at rt under nitrogen, this was added to the reaction mixture and left stirring at rt for 3 days. Water was added (40 mL) and the organic product was extracted with ethyl acetate. The organic layer was washed with brine, dried through a hydrophobic frit and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 0-20 percent ethyl acetate in cyclohexane. Fractions containing product were
Reference: [1] Patent: WO2014/78257, 2014, A1, . Location in patent: Page/Page column 117
[2] Patent: WO2014/140077, 2014, A1, . Location in patent: Page/Page column 48
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