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[ CAS No. 903131-13-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 903131-13-5
Chemical Structure| 903131-13-5
Chemical Structure| 903131-13-5
Structure of 903131-13-5 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 903131-13-5 ]

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Product Details of [ 903131-13-5 ]

CAS No. :903131-13-5 MDL No. :MFCD07787361
Formula : C9H5BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :PMIGAISGWPTELT-UHFFFAOYSA-N
M.W : 221.05 Pubchem ID :2763232
Synonyms :

Calculated chemistry of [ 903131-13-5 ]

Physicochemical Properties

Num. heavy atoms : 12
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 : 50.71
TPSA : 39.58 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) : -5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 2.46
Log Po/w (WLOGP) : 2.8
Log Po/w (MLOGP) : 1.6
Log Po/w (SILICOS-IT) : 3.15
Consensus Log Po/w : 2.32

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.32
Solubility : 0.107 mg/ml ; 0.000484 mol/l
Class : Soluble
Log S (Ali) : -2.94
Solubility : 0.257 mg/ml ; 0.00116 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.23
Solubility : 0.013 mg/ml ; 0.000059 mol/l
Class : Moderately soluble

Medicinal Chemistry

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

Safety of [ 903131-13-5 ]

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 [ 903131-13-5 ]

* 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 [ 903131-13-5 ]

[ 903131-13-5 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 52488-36-5 ]
  • [ 1189-71-5 ]
  • [ 903131-13-5 ]
YieldReaction ConditionsOperation in experiment
87% Example 14 Synthesis of 4-bromo-1H-indole-3-carbonitrile (LVII) To a 0 C. solution of 4-bromoindole (5 g, 25.5 mmol) in acetonitrile (50 ml) was added dropwise chlorsulfonylisocyanate (2.37 ml, 27.3 mmol) over a 5 minute period. The reaction mixture was stirred at 0 C. for 2 hours, and TEA (3.77 ml, 27.0) was added dropwise over a 10 minute period. The reaction mixture was allowed reach room temperature overnight, poured into ice/water mixture (200 ml), and the aqueous layer was extracted with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, concentrated, and purified by flash chromatography to afford 4-bromo-1H-indole-3-carbonitrile LVII as an off-white solid (4.9 g, 87% yield).
  • 2
  • [ 903131-13-5 ]
  • [ 4192-77-2 ]
  • 3-(3-cyano-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With tetrabutylammomium bromide; triethylamine;dichlorobis(tri-O-tolylphosphine)palladium; at 110℃; for 20.0h; Synthesis of 3-(3-Cyano-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester (LVIII) A mixture of <strong>[903131-13-5]4-bromo-1H-indole-3-carbonitrile</strong> LVII (2 g, 9.05 mmol), ethyl cinammate (3.19 g, 18.1 mmol), tetrabutylammonium bromide (582 mg, 1.81 mmol), TEA (2.52 ml, 18.1 mmol) and palladium-dichloro-[bis-(tri-ortho-tolyl)phophine] (357 mg, 0.453 mmol) in a sealed vial was stirred at 110 C. for 20 hours. The reaction mixture was cooled to room temperature, partitioned between H2O and DCM, and the aqueous layer was extracted with DCM. The organic extracts were combined, dried over Na2SO4, filtered, concentrated, and purified via flash chromatography (hexane/EtOAc) affording 3-(3-cyano-1H-Indol-4-yl)-3-phenyl-acrylic acid ethyl ester LVIII as a yellow solid (1.57 g, 55% yield).
  • 3
  • [ 903131-13-5 ]
  • [ 73183-34-3 ]
  • 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 19.0h;Inert atmosphere; To a mixture of <strong>[903131-13-5]4-bromo-1H-indole-3-carbonitrile</strong> (905 mg, 4.09 mmol, 1.0 eq.), bis(pinacolato)diboron (1.14 g, 1.1 eq.), potassium acetate (1.21 g, 3.0 eq.) and PdCI2(dppf) (300 mg, 0.1 eq.) was added 1,4-dioxane (30 mL). The resultantsuspension was degassed by vac-purging and heated to 90C for 19 h. The reaction mixture was partitioned between EtOAc (100 mL), water (30 mL) and brine (30 ml). The aqueous phase was re-extracted with EtOAc (3 x 25 mL) and the combined organics were dried over MgSO4. The drying agent was removed by filtration and the solvent removed in vacuo to afford a viscous brown oil thatwas purified by flash chromatography on silica with CH2CI2/EtOAc (1:0-9:1) to afford orange solids (616 mg). Material dissolved in EtOAc (24 mL) and treated with activated carbon (180 mg) at 85 C for 4 h before filtering and removal of solvent in vacuo to afford Intermediate 60 as a pale orange solid (555 mg,50%).1H NMR (DMSO-d5) oH. 12.22 (brs, 1H), 8.28 (d, J=3.0 Hz, 1H), 7.64 (dd, J=8.1,1.1 Hz, 1H), 7.49 (dd, J=7.1, 1.0 Hz, 1H), 7.26 (dd, J=8.2, 7.1 Hz, 1H), 1.35 (5,12H).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 27.0h;Reflux; Intermediate 118: 4-f4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)-l -indole-3- carbonitrile (0806) (0807) A mixture of 4-bromo-l/7i-indole-3-carbonitrile (500.3 mg, 2.26 mmol), 4,4,4',4',5,5,5',5'- octamethyl-2,2'-bi(l,3,2-dioxaborolane) (694.3 mg, 2.73 mmol), [1,1'- 7 s(diphenylphosphino)ferrocene]dichloropalladium(II) (169.6 mg, 0.23 mmol) and potassium acetate (668.8 mg, 6.81 mmol) in 1,4-dioxane (12 mL) was stirred at reflux for 21.5 h. Further 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (288.4 mg, 1.14 mmol) was added after 5.5 h. The mixture was removed from heating and left to cool to rt, after which it was filtered through a 10 g Celite cartridge. This was washed with ethyl acetate (approx. 3 x 10 mL). To the filtrate was added water (10 mL) and brine (30 mL) and the layers separated. The aqueous layer was extracted with further ethyl acetate (2 x 30 mL) and the organic layers combined and filtered through a cartridge fitted with a hydrophobic frit. The filtrate was evaporated in vacuo, redissolved in dichloromethane (approx. 10 mL) and directly applied to the top of a 100 g SNAP cartridge and purified by flash column chromatography. The column was eluted with a gradient of 0% - 40% ethyl acetate in cyclohexane. The required fractions were combined and evaporated in vacuo to give 4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-l indole-3-carbonitrile (80 wt% purity, 481.8 mg, 1.44 mmol, 64 % yield) as a viscous yellow oil which formed light yellow crystals upon standing. (0808) LCMS (2 min High pH): Rt = 1.08 min, [M-H]- = 269.3.
  • 4
  • [ 903131-13-5 ]
  • 4-[6-(morpholin-4-yI)-12-[(1-oxo-1λ4-thiomorpholin-4-yI)methyl]-8-oxa-3,5,10-triazatricyclo-[7.4.0.02,7]trideca1(13),2(7),3,5,9,11-hexaen-4-yl]-1H-indole-3-carbonitrile [ No CAS ]
  • 5
  • [ 903131-13-5 ]
  • N4-((1R,5S,6r)-3-oxabicyclo[3.1.0]hexan-6-yl)-6-((3-cyano-1H-indol-4-yl)methyl)-N2-methylpyridine-2,4-dicarboxamide [ No CAS ]
  • 6
  • [ 52488-36-5 ]
  • [ 135205-66-2 ]
  • [ 903131-13-5 ]
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