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[ CAS No. 1034467-80-5 ] {[proInfo.proName]}

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Chemical Structure| 1034467-80-5
Chemical Structure| 1034467-80-5
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Product Details of [ 1034467-80-5 ]

CAS No. :1034467-80-5 MDL No. :MFCD18384289
Formula : C8H8FN Boiling Point : -
Linear Structure Formula :- InChI Key :HDIKFKIIABQSPW-UHFFFAOYSA-N
M.W : 137.15 Pubchem ID :57690831
Synonyms :

Calculated chemistry of [ 1034467-80-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.66
TPSA : 12.89 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) : -5.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.0
Log Po/w (XLOGP3) : 2.2
Log Po/w (WLOGP) : 2.46
Log Po/w (MLOGP) : 1.91
Log Po/w (SILICOS-IT) : 2.86
Consensus Log Po/w : 2.28

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.45
Solubility : 0.482 mg/ml ; 0.00351 mol/l
Class : Soluble
Log S (Ali) : -2.1
Solubility : 1.08 mg/ml ; 0.00786 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.87
Solubility : 0.184 mg/ml ; 0.00134 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 1034467-80-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1034467-80-5 ]

* 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 [ 1034467-80-5 ]
  • Downstream synthetic route of [ 1034467-80-5 ]

[ 1034467-80-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 171197-80-1 ]
  • [ 411235-57-9 ]
  • [ 1034467-80-5 ]
YieldReaction ConditionsOperation in experiment
63% With potassium phosphate In water; toluene at 100℃; for 4 h; Preparation 46; 5-Cyclopropyl-2-fluoro-pyridine; In a flask, combine 2-fluoro-5-iodo-pyridine (1.12 g, 5 mmol), cyclopropylboronic acid (645 mg, 7.5 mmol), palladium acetate (56 mg, 0.25 mmol), potassium phosphate (3.2 g, 15 mmol), and toluene-water (20: 1, 21 mL). Heat the mixture at 100 0C for 4 hours. Dilute the mixture with chloroform-isopropanol (3: 1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (20 percent ethyl acetate in hexane) to afford the title compound (430 mg, 63 percent) as a pale yellow oil. 1H νMR (400 MHz-CDCl3) δ 7.99 (d, J= 3 Hz, IH), 7.39 (td, J= 3, 5 Hz, IH), 6.79 (dd, J= 3, 8 Hz, IH), 0.96-1.02 (m, 2H), 0.63-0.69 (m, 2H).
63% With potassium phosphate In water; toluene at 100℃; for 4 h; Preparation 145-Cyclopropyl-2-fluoro-pyridineCombine 2-fluoro-5-iodo-pyridine (1.12 g, 5 mmol), cyclopropylboronic acid (645 mg, 7.5 mmol), palladium acetate (56 mg, 0.25 mmol) and potassium phosphate (3.2 g, 15 mmol) in toluene/water (20: 1, 21 mL). Heat the mixture at 100 0C for 4 h. Dilute the mixture with chloroform-IPA (3:1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (20 percent ethyl acetate in hexane) to afford the title compound as a pale yellow oil (430 mg, 63 percent).
Reference: [1] Patent: WO2008/76705, 2008, A1, . Location in patent: Page/Page column 19
[2] Patent: WO2008/144222, 2008, A2, . Location in patent: Page/Page column 13
  • 2
  • [ 766-11-0 ]
  • [ 411235-57-9 ]
  • [ 1034467-80-5 ]
YieldReaction ConditionsOperation in experiment
647 mg With potassium phosphate; palladium diacetate; tricyclohexylphosphine In water; toluene at 80℃; for 16 h; Inert atmosphere 5-Bromo-2-fluoro - pyridine (1.41 g, 8 mmol) and cyclopropyl boronicacid (1.37 g, 16 mmol) mixed in toluene / water (26 mL / 1.3 mL), to which was added potassium phosphate (7.46 Under g, 28 mmol), argon was added theretopalladium acetate (90 mg, 0.4 mmol) and tricyclohexylphosphine (224 mg, 0.8mmol), the mixture was heated to 80  °C the reaction 16h. After completion of the reaction by TLC, cooled to room temperature,water was added thereto, extracted with ethyl acetate, the organic phase wasdried over anhydrous sodium sulfate, filtered, and the solvent was evaporatedto dryness, purified by silica gel column chromatography to give 5-cyclopropyl-2-fluoro- pyridine (yellow oil, 647 mg). 
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5579 - 5598
[2] Patent: CN103420977, 2016, B, . Location in patent: Paragraph 0229-0232
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