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[ CAS No. 1305208-17-6 ] {[proInfo.proName]}

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Chemical Structure| 1305208-17-6
Chemical Structure| 1305208-17-6
Structure of 1305208-17-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1305208-17-6 ]

CAS No. :1305208-17-6 MDL No. :MFCD20923312
Formula : C6H3BrIN3 Boiling Point : -
Linear Structure Formula :- InChI Key :QYKRPCLDVYDBLC-UHFFFAOYSA-N
M.W : 323.92 Pubchem ID :56923655
Synonyms :

Calculated chemistry of [ 1305208-17-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 54.31
TPSA : 41.57 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) : -6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.23
Log Po/w (XLOGP3) : 1.95
Log Po/w (WLOGP) : 2.32
Log Po/w (MLOGP) : 1.85
Log Po/w (SILICOS-IT) : 3.21
Consensus Log Po/w : 2.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.68
Solubility : 0.0673 mg/ml ; 0.000208 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 1.16 mg/ml ; 0.00357 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.32
Solubility : 0.0156 mg/ml ; 0.0000482 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.23

Safety of [ 1305208-17-6 ]

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 [ 1305208-17-6 ]

* 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 [ 1305208-17-6 ]

[ 1305208-17-6 ] Synthesis Path-Downstream   1~8

YieldReaction ConditionsOperation in experiment
1.02 g With iodine; potassium hydroxide In N,N-dimethyl-formamide at 1 - 40℃; for 1h; 48.1 (1) Synthesis of 6-bromo-3-iodo-1H-indazole [36-1] (hereinafter referred to as a compound [36-1]) General procedure: (1) Synthesis of 6-bromo-3-iodo-1H-indazole [36-1] (hereinafter referred to as a compound [36-1]) To a solution of 6-bromo-1H-indazole (1.11 g) in N,N-dimethylformamide (10 mL) were added iodine (2.17 g) and potassium hydroxide (1.14 g), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was quenched with water, and extracted with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (1.45 g) as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ: 11.22 (1H, s), 7.71 (1H, s), 7.39-7.31 (2H, m).
  • 2
  • [ 1305208-17-6 ]
  • [ 2640092-74-4 ]
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 / 0 - 20 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; 1,4-dioxane / 1 h / 70 °C / Inert atmosphere
  • 3
  • [ 1305208-17-6 ]
  • [ 2640092-77-7 ]
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 / 0 - 20 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; 1,4-dioxane / 1 h / 70 °C / Inert atmosphere 3.1: caesium carbonate; RuPhos precatalyst chloro(2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(ll) / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere
  • 4
  • [ 1305208-17-6 ]
  • [ 2640092-78-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 1.2: 2 h / 0 - 20 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; 1,4-dioxane / 1 h / 70 °C / Inert atmosphere 3.1: caesium carbonate; RuPhos precatalyst chloro(2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(ll) / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h / 20 °C
  • 5
  • [ 1305208-17-6 ]
  • [ 2640092-80-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 1.2: 2 h / 0 - 20 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; 1,4-dioxane / 1 h / 70 °C / Inert atmosphere 3.1: caesium carbonate; RuPhos precatalyst chloro(2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(ll) / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h / 20 °C 5.1: caesium carbonate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / water; 1,4-dioxane / 1 h / 70 °C / Inert atmosphere
  • 6
  • [ 1305208-17-6 ]
  • [ 76-83-5 ]
  • [ 2640092-72-2 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-bromo-3-iodo-1H-pyrazolo[4,3-b]pyridine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: trityl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 2h; 34.2 Step 2. Step 2. 6-Bromo-3-iodo-1-trityl-1H-pyrazolo[4,3-b]pyridine To a suspension of NaH (1.63 g, 40.8 mmol) in DMF (100 ml) at 0° C. was added a solution of 6-bromo-3-iodo-1H-pyrazolo[4,3-b]pyridine (12.0 g, 37.0 mmol) in 20 ml of DMF dropwise. After the addition was complete, the reaction mixture was warmed to r.t and stirred at that temperature for 30 min. The mixture was then cooled back to 0° C. and treated with a solution of (chloromethanetriyl)tribenzene (11.4 g, 40.8 mmol) in 20 ml of DMF. The reaction mixture was stirred at r.t for 2 h. Water was then added and the product was extracted with DCM. The organic phase was concentrated in vacuo. The resultant solid was collected by filtration and air-dried. LC-MS calculated for C25H18BrIN3 (M+H)+: m/z=566.0; found 566.0.
  • 7
  • [ 1305208-17-6 ]
  • [ 2640088-71-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 1.2: 2 h / 0 - 20 °C 2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; 1,4-dioxane / 1 h / 70 °C / Inert atmosphere 3.1: caesium carbonate; RuPhos precatalyst chloro(2-dicyclohexylphosphino-2',6'-diisopropoxy-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(ll) / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 4.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h / 20 °C 5.1: caesium carbonate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / water; 1,4-dioxane / 1 h / 70 °C / Inert atmosphere 6.1: dichloromethane / 1 h / 20 °C
  • 8
  • [ 1150617-54-1 ]
  • [ 1305208-17-6 ]
YieldReaction ConditionsOperation in experiment
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 2h; 34.1 Step 1. Step 1. 6-Bromo-3-iodo-1H-pyrazolo[4,3-b]pyridine To a solution of 6-bromo-1H-pyrazolo[4,3-b]pyridine (8.0 g, 40.4 mmol) in 60 ml of DMF was added 1-iodopyrrolidine-2,5-dione (7.69 g, 44.4 mmol), and the reaction mixture was stirred at r.t for 2 h. The mixture was poured into water (300 ml) and was stirred for another 10 min. The resulting solid was collected by filtration and was washed with water. It was air-dried and used in the next step without further purification. LC-MS calculated for C6H4BrIN3 (M+H)+: m/z=323.9; found 323.9.
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