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[ CAS No. 1227493-96-0 ] {[proInfo.proName]}

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Chemical Structure| 1227493-96-0
Chemical Structure| 1227493-96-0
Structure of 1227493-96-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1227493-96-0 ]

CAS No. :1227493-96-0 MDL No. :MFCD16609917
Formula : C8H5BrFN Boiling Point : -
Linear Structure Formula :- InChI Key :CIRXFJXMJOVFMR-UHFFFAOYSA-N
M.W : 214.03 Pubchem ID :70829137
Synonyms :

Calculated chemistry of [ 1227493-96-0 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 45.96
TPSA : 15.79 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) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.86
Log Po/w (XLOGP3) : 2.84
Log Po/w (WLOGP) : 3.49
Log Po/w (MLOGP) : 2.73
Log Po/w (SILICOS-IT) : 3.62
Consensus Log Po/w : 2.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.56
Solubility : 0.0587 mg/ml ; 0.000274 mol/l
Class : Soluble
Log S (Ali) : -2.83
Solubility : 0.317 mg/ml ; 0.00148 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.42
Solubility : 0.00812 mg/ml ; 0.0000379 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 1227493-96-0 ]

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 [ 1227493-96-0 ]

* 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.

  • Downstream synthetic route of [ 1227493-96-0 ]

[ 1227493-96-0 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1427502-92-8 ]
  • [ 4637-24-5 ]
  • [ 1227493-96-0 ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: 2-bromo-1-fluoro-3-methyl-4-nitrobenzene; <i>N</i>,<i>N</i>-dimethyl-formamide dimethyl acetal In 1,4-dioxane; 1-methyl-pyrrolidin-2-one at 100℃; for 18h; Stage #2: With iron; acetic acid for 2h; Reflux; Step 2 To a stirring solution of 2-bromo-1-fluoro-3-methyl-4-nitrobenzene (3.0 g, 12.68 mmol, 1 eq) in 1,4-dioxane (25 mL) were slowly added N,N-dimethylformamide dimethylacetal (7.6 g, 64.10 mmol, 5 eq) and pyrrolidine (0.9 g, 12.82 mmol, 1eq), and the reaction mixture was stirred for 18 h at 100°C. The reaction mixture was then concentrated and to the residue were added acetic acid (30 mL) and iron powder (7.17 g, 128 mmol, 10 eq). The reaction mixture was refluxed for 2 h, cooled to room temperature and filtered through a celite bed. The filtrate was neutralised by 50% sodium hydroxide solution and extracted by ethyl acetate (2 x 250 mL). The combined organic layers were washed with water (100 mL) and brine (100 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The cmde residue was purified by column chromatography (230-400 mesh silica gel; 20% ethyl acetate/hexane) to afford compound 4-bromo-5-fluoro-1H-indole (1.7 g, 63%) as a brown liquid.
  • 2
  • [ 1227493-96-0 ]
  • [ 2668261-97-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C
  • 3
  • [ 1227493-96-0 ]
  • [ 2668261-98-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 1.2: 2 h / 20 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C 3.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 16 h / 90 °C / Inert atmosphere
  • 4
  • [ 1227493-96-0 ]
  • [ 86864-60-0 ]
  • [ 2668261-96-7 ]
YieldReaction ConditionsOperation in experiment
98% Stage #1: 4-bromo-5-fluoro-1H-indole With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: 2-(tert-butyldimethylsilyloxy)ethyl bromide In N,N-dimethyl-formamide at 20℃; for 2h; Step 3 To a solution of 4-bromo-5-fluoro-1H-indole (0.5 g, 2.336 mmol, 1 eq.) in DMF (5 mL) was added sodium hydride (0.130 g, 2.80 mmol, 1.2 eq) at 0°C, and the solution was stirred at RT for half an hour, followed by addition of (2-bromoethoxy)(tert-butyl)dimethylsilane (1.17 g, 4.67 mmol, 2.0 eq) and the reaction mixture was stirred at RT for 2 h. After completion (monitored by LCMS), the reaction mixture was diluted with ethyl acetate (20 mL) and the organic layer was washed with cold water (5 x 10 mL) and brine (10 mL), dried over anhydrous Na2SO4 and evaporated under reduced pressure. The cmde residue was purified by column chromatography to afford 4-bromo-1-{2-[(tert- butyldimethylsilyl)oxy]ethyl}-5-fluoro-1H-indole (0.85 g, 98%) as a brown liquid.
  • 5
  • [ 59907-13-0 ]
  • [ 1227493-96-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: acetic acid; nitric acid / 2 h / 20 - 80 °C 2.1: 1,4-dioxane; 1-methyl-pyrrolidin-2-one / 18 h / 100 °C 2.2: 2 h / Reflux
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