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[ CAS No. 205114-16-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 205114-16-5
Chemical Structure| 205114-16-5
Chemical Structure| 205114-16-5
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Product Details of [ 205114-16-5 ]

CAS No. :205114-16-5 MDL No. :MFCD22690570
Formula : C9H5BrFN Boiling Point : -
Linear Structure Formula :- InChI Key :BDFONODCJLSXEP-UHFFFAOYSA-N
M.W : 226.05 Pubchem ID :18186204
Synonyms :

Calculated chemistry of [ 205114-16-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 49.4
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) : -5.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.23
Log Po/w (XLOGP3) : 3.13
Log Po/w (WLOGP) : 3.56
Log Po/w (MLOGP) : 2.98
Log Po/w (SILICOS-IT) : 3.54
Consensus Log Po/w : 3.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.83
Solubility : 0.0334 mg/ml ; 0.000148 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.192 mg/ml ; 0.000851 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.84
Solubility : 0.00327 mg/ml ; 0.0000145 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 205114-16-5 ]

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 [ 205114-16-5 ]

* 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.

  • Downstream synthetic route of [ 205114-16-5 ]

[ 205114-16-5 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 399-52-0 ]
  • [ 75-25-2 ]
  • [ 205114-16-5 ]
YieldReaction ConditionsOperation in experiment
15% With N-benzyl-N,N,N-triethylammonium chloride In water; toluene at 40℃; for 48h; Intermediate 36: 3-bromo-6-fluoroquinoline To a solution of 5-Fluoroindole (2.00 g, 14.8 mmol) and benzyltriethylammonium chloride (168.5 mg, 0.740 mmol) in toluene (3.00 mL) and bromoform (3.00 mL) at 40 °C was added a solution of sodium hydroxide (4.44 g, 1 1 1 mmol) in water (12.0 mL) in a dropwise manner. The reaction then stirred at 40 °C for 48 h. After cooling, the solvent was evaporated and the residue was diluted with methyl tert-butyl ether (100 mL) and water (100 mL). The aqueous layer was extracted with methyl tert-butyl ether. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give 2.00 g of crude material. Purification by silica gel flash chromatography (0-2% ethyl acetate in petroleum ether) provided 3-bromo-6- fluoroquinoline (503 mg, 15% yield) as a white solid. 1 H NMR (400 MHz, CD3OD, δ):8.87 (d, J = 2.0 Hz, 1 H), 8.27 (d, J = 2.0 Hz, 1 H), 8.08 (dd, J = 9.2, 5.6 Hz, 1 H), 7.52 - 7.41 (m, 1 H), 7.35 (dd, J = 8.8, 2.8 Hz, 1 H). (M+1 ): 225.6.
  • 2
  • [ 1421348-79-9 ]
  • [ 205114-16-5 ]
  • [ 1421348-83-5 ]
YieldReaction ConditionsOperation in experiment
5.3% With chloro(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(ll); potassium <i>tert</i>-butylate In tetrahydrofuran for 18h; Reflux; Intermediate 40: tert-butyl 4-((3,3-dimethylcyclobutyl)(6-fluoroquinolin-3-ylamino) methyl)benzoate To a solution containing 2-(dicyclohexylphosphino)-3,6-dimethoxy-2'-4'-6'-tri-i- propyl-1 , 1 '-biphenyl (16.3 mg, 0.0300 mmol), chloro(2-dicyclohexylphosphino-3,6- dimethoxy-2',4',6'-triisopropyl-1 , 1 '-biphenyl)[2-(2-aminoethyl)phenyl]palladium(ll) (25.0 mg, 0.0300 mmol) and 3-bromo-6-fluoroquinoline (164 mg, 0.670 mmol) was added anhydrous tetrahydrofuran (6.00 ml.) and tert-butyl 4-(amino(3,3- dimethylcyclobutyl)methyl)benzoate (175 mg, 0.600 mmol). The mixture was warmed gently and then potassium tert-butoxide (150 mg, 1.30 mmol) was added as a solid. The reaction was then heated at reflux for 18 h. The reaction was then cooled to room temperature and quenched with saturated aqueous ammonium chloride and extracted three times with ethyl acetate. The combined organic layers were dried with sodium sulfate, filtered, and concentrated to give 401 mg of a red oil. Purification by silica gel flash chromatography (0-50% ethyl acetate in heptane) afforded tert-butyl 4-((3,3- dimethylcyclobutyl)(6-fluoroquinolin-3-ylamino)methyl) benzoate (14.0 mg, 5.3% yield) as a brown oil. 1 H NMR (400 MHz, CDCI3, δ): 8.43 (s, 1 H), 7.97 - 7.92 (m, 2H), 7.86 (dd, J = 9.1 , 5.8 Hz, 1 H), 7.43 - 7.37 (m, 2H), 7.10 (td, J = 8.7, 2.7 Hz, 1 H), 7.01 (dd, J = 9.6, 2.7 Hz, 1 H), 6.61 (d, J = 2.5 Hz, 1 H), 4.25 (dd, J = 9.3, 4.6 Hz, 1 H), 2.59 - 2.46 (m, 1 H), 2.00 (s, 1 H), 1 .76 - 1 .67 (m, 2H), 1 .66 - 1.58 (m, 1 H), 1 .56 (s, 9H), 1 .13 (s, 3H), 1 .09 (s, 3H). MS (M+1 ): 435.3.
  • 3
  • [ 205114-16-5 ]
  • [ 1421348-50-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: chloro(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(ll); potassium <i>tert</i>-butylate / tetrahydrofuran / 18 h / Reflux 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 18 h 4: sodium hydroxide / tetrahydrofuran; methanol / 4.5 h / 20 °C
  • 4
  • [ 205114-16-5 ]
  • [ 1421348-84-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: chloro(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(ll); potassium <i>tert</i>-butylate / tetrahydrofuran / 18 h / Reflux 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
  • 5
  • [ 205114-16-5 ]
  • [ 1421348-85-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: chloro(2-dicyclohexylphosphino-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2-aminoethyl)phenyl]palladium(ll); potassium <i>tert</i>-butylate / tetrahydrofuran / 18 h / Reflux 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole / dichloromethane / 18 h
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