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[ CAS No. 188057-35-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 188057-35-4
Chemical Structure| 188057-35-4
Chemical Structure| 188057-35-4
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Product Details of [ 188057-35-4 ]

CAS No. :188057-35-4 MDL No. :MFCD11977407
Formula : C5H3BrINO Boiling Point : -
Linear Structure Formula :- InChI Key :AVAHPXWHVGKFQN-UHFFFAOYSA-N
M.W : 299.89 Pubchem ID :19597708
Synonyms :

Calculated chemistry of [ 188057-35-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.68
TPSA : 33.12 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) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 2.21
Log Po/w (WLOGP) : 2.15
Log Po/w (MLOGP) : 1.52
Log Po/w (SILICOS-IT) : 2.59
Consensus Log Po/w : 2.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.58
Solubility : 0.078 mg/ml ; 0.00026 mol/l
Class : Soluble
Log S (Ali) : -2.54
Solubility : 0.865 mg/ml ; 0.00288 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.24
Solubility : 0.172 mg/ml ; 0.000574 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.39

Safety of [ 188057-35-4 ]

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 [ 188057-35-4 ]

* 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 [ 188057-35-4 ]

[ 188057-35-4 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 188057-35-4 ]
  • [ 108-24-7 ]
  • [ 1215106-72-1 ]
YieldReaction ConditionsOperation in experiment
100% at 130℃; for 0.5h; Step 2: Preparation of 6-bromo-2-iodopyridin~3-yl acetate. 6-bromo-2-iodopyridin- 3-ol (150 mg, 0.500 mmol) was added to acetic anhydride (2.4 mL, 25 mmol) at 130 0C. It was allowed to stir for 30 min then concentrated and chased with toluene to give the expected product 6-bromo-2-iodopyridm-3-yl acetate (171 mg, 0.500 mmol, 100 % yield) by NMR. IH NMR (400 MHz, DMSO-d6) δ ppm 7.74 (1 H, d, J=8.28 Hz), 7.62 (1 H, d, J-8.28 Hz), 2.36 (3 H, s). LC-MS retention time: 1.66 min; m/z (MH+): 342, 344. LC data was recorded on a Shimadzu LC-IOAS liquid chromatograph equipped with a Waters SunFire 5u Cl 8 4, 6x5 Omm column using a SPD-IOAV UV- Vis detector at a detector wave length of 22OnM.. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% acetonitrile / 90% H2O / 0.1% trifluoroacetic acid and solvent B was 10% H2O / 90% acetonitrile / 0,1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.
100% at 130℃; for 0.5h; 2 6-bromo-2-iodopyridin- 3-ol (150 mg, 0.500 mmol) was added to acetic anhydride (2.4 mL, 25 mmol) at 130 °C. It was allowed to stir for 30 min then concentrated and chased with toluene to give the expected product 6-bromo-2-iodopyridin-3-yl acetate (171 mg, 0.500 mmol, 100 % yield) by NMR. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.74 (1 H, d, J=8.28 Hz), 7.62 (1 H, d, J=8.28 Hz), 2.36 (3 H, s). LC-MS retention time: 1.66 min; m/z (MH+): 342, 344. LC data was recorded on a Shimadzu LC-10AS liquidchromatograph equipped with a Waters SunFire 5u C18 4.6x50mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% acetonitrile / 90% H20 / 0.1% trifluoroacetic acid and solvent B was 10% H20 / 90% acetonitrile / 0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.
95% at 130℃; for 0.5h; 1.37.2 Step 2: 6-bromo-2-iodopyridin-3-yl acetate Step 2: 6-bromo-2-iodopyridin-3-yl acetate [0286] To a heated acetic anhydride (33 mL) solution at 130 °C was added 6-bromo-2-iodopyridin-3-ol (2.00 g, 6.67 mmol) in one portion. After stirring for 30 min at 130 °C, the mixture was allowed to cool and the acetic anhydride solvent was removed in vacuo. The concentrate was dissolved in EtOAc, washed with saturated aqueous NaHC03, brine, dried over Na2S04, and concentrated under vacuum to afford the title compound as an off-white powder (2.16 g, 95%). MS (ESI) calcd for C7H5BrlN02: 340.9; found: 341.8 and 343.8 [M+H]. *H NMR (400 MHz, CDCI3) δ 7.45 (d, J = 8.0 Hz, 1H), 7.23 (d, J = 8.0 Hz, 1H), 2.40 (s, 3H).
  • 2
  • [ 55717-45-8 ]
  • 6-bromo-2-iodopyridin-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With iodine; potassium carbonate; In tetrahydrofuran; at 20℃; Potassium carbonate (3.18 g, 22.98 mmol, 2.0 equiv) and <strong>[55717-45-8]2-bromo-5-hydroxypyridine</strong> (0501-98) (2.0 g, 11.49 mmol, 1.0 equiv)Dissolved in 50 ml of tetrahydrofuran,Iodine (6.41 g, 25.28 mmol, 2.2 eq.) was added and stirred overnight at room temperature.After the reaction was completed, 25 ml of an aqueous solution of sodium bisulfite was added. Finally, the mixture was extracted with ethyl acetate, and the organic phase was washed with saturated brine and concentrated under reduced pressure.An off-white solid product, 6-bromo-3-hydroxy-2-iodopyridine (3.24 g, yield: 94%) was obtained.
37% With N-iodo-succinimide; In methanol; at 45℃; for 3h; Step 1: Preparation of 6-bromo-2-iodopyridin-3-ol. N-iodosuccinimide (6.47 g, 28.7 mmol) was added to a stirring solution of <strong>[55717-45-8]6-bromopyridin-3-ol</strong> (5 g, 28.7 mmol) in MeOH (144 mL) at 45 0C. It was allowed to stir for 3 hours. The mixture was concentrated and triturated with Et20. The precipitate was discarded and the filtrate was concentrated and triturated with dichloromethane to give the expected product, 1 6-bromo-2-iodopyridin-3-ol (3150 mg, 10.50 mmol, 37 % yield) by LCMS and NMR. IH NMR (400 MHz, DMSOdbeta) delta ppm 11.12 (1 H, s), 7.42 (1 H, d, J=8.28 Hz)5 7.10 (1 H, d, J=8.28 Hz). LC-MS retention time: 1.27 min; m/z (MH+): 300, 302. LC data was recorded on a Shimadzu LC-IOAS liquid chromatograph equipped with a Waters SunFire 5u C18 4.6x50mm column using a SPD-10AV UV- Vis detector at a detector wave length of 22OnM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% acetonitrile / 90% H2O / 0.1% trifluoroacetic acid and solvent B was 10% H2O / 90% acetonitrile / 0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.
37% With N-iodo-succinimide; In methanol; at 45℃; for 3h; N-iodosuccinimide (6.47 g, 28.7 mmol) was added to a stirring solution of <strong>[55717-45-8]6-bromopyridin-3-ol</strong> (5 g, 28.7 mmol) in MeOH (144 mL) at 45 C. It was allowed to stir for 3 hours. The mixture was concentrated and triturated with Et20. The precipitate was discarded and the filtrate was concentrated and triturated with dichloromethane to give the expected product, 16- bromo-2-iodopyridin-3-ol (3150 mg, 10.50 mmol, 37 % yield) by LCMS and NMR. lH MR (400 MHz, DMSO-d6) delta ppm 1 1.12 (1 H, s), 7.42 (1 H, d, J=8.28Hz), 7.10 (1 H, d, J=8.28 Hz). LC-MS retention time: 1.27 min; m/z (MH+): 300, 302. LC data was recorded on a Shimadzu LC-10AS liquid chromatograph equipped with a Waters SunFire 5u C18 4.6x50mm column using a SPD-10AV UV-Vis detector at a detector wave length of 220nM. The elution conditions employed a flow rate of 5 ml/min, a gradient of 100% solvent A / 0% solvent B to 0% solvent A / 100% solvent B, a gradient time of 3 min, a hold time of 1 min, and an analysis time of 4 min where solvent A was 10% acetonitrile / 90% H20 / 0.1% trifluoroacetic acid and solvent B was 10%> H20 / 90%> acetonitrile / 0.1% trifluoroacetic acid. MS data was determined using a Micromass Platform for LC in electrospray mode.
30% With N-iodo-succinimide; In methanol; at 45℃; for 5h; Step 1: 6-bromo-2-iodopyridin-3-ol [0285] A solution of <strong>[55717-45-8]6-bromopyridin-3-ol</strong> (8.00 g, 46.0 mmol) and N-iodosuccinimide (10.34 g, 46.0 mmol) in methanol (180 mL) was heated at 45 C for 5 hours with stirring. The mixture was allowed to cool to room temperature and the solvent was removed under reduced pressure. The resulting solid was triturated with ether and collected by filtration. The solid prooduct was further triturated with DCM and dried to afford the title product as a pale pink powder (4.26 g, 30%). MS (ESI) calcd for C5H3BrlNO: 298.8; found: 301.8 [M+H]. *H NM (400 MHz, CDCI3) delta 7.31 (d, J = 8.0 Hz, 1H), 7.10 (d, 7 = 8.0 Hz, 1H), 5.45 (s, 1H).

  • 3
  • [ 188057-35-4 ]
  • [ 1215106-71-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 0.5 h / 130 °C 2: triethylamine; copper(l) iodide / trans-bis(triphenylphosphine)palladium dichloride / 2 h / 85 °C / Inert atmosphere 3: potassium carbonate; sodium acetate; copper(II) choride dihydrate / palladium dichloride / 20 °C / 15514.9 Torr / Parr bomb 4: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 60 °C 5: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide; tetrahydrofuran / 1 h
  • 4
  • [ 188057-35-4 ]
  • [ 1215107-65-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 0.5 h / 130 °C 2: triethylamine; copper(l) iodide / trans-bis(triphenylphosphine)palladium dichloride / 2 h / 85 °C / Inert atmosphere 3: potassium carbonate; sodium acetate; copper(II) choride dihydrate / palladium dichloride / 20 °C / 15514.9 Torr / Parr bomb 4: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 60 °C
  • 5
  • [ 188057-35-4 ]
  • [ 1215105-46-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 0.5 h / 130 °C 2: triethylamine; copper(l) iodide / trans-bis(triphenylphosphine)palladium dichloride / 2 h / 85 °C / Inert atmosphere 3: potassium carbonate; sodium acetate; copper(II) choride dihydrate / palladium dichloride / 20 °C / 15514.9 Torr / Parr bomb 4: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 60 °C 5: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide; tetrahydrofuran / 1 h 6: caesium carbonate; sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate / palladium diacetate / N,N-dimethyl-formamide; water / 1 h / 60 °C 7: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C
  • 6
  • [ 188057-35-4 ]
  • [ 1215107-71-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 0.5 h / 130 °C 2: triethylamine; copper(l) iodide / trans-bis(triphenylphosphine)palladium dichloride / 2 h / 85 °C / Inert atmosphere 3: potassium carbonate; sodium acetate; copper(II) choride dihydrate / palladium dichloride / 20 °C / 15514.9 Torr / Parr bomb 4: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 60 °C 5: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide; tetrahydrofuran / 1 h 6: caesium carbonate; sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate / palladium diacetate / N,N-dimethyl-formamide; water / 1 h / 60 °C
  • 7
  • [ 188057-35-4 ]
  • [ 1215105-48-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 0.5 h / 130 °C 2: triethylamine; copper(l) iodide / trans-bis(triphenylphosphine)palladium dichloride / 2 h / 85 °C / Inert atmosphere 3: potassium carbonate; sodium acetate; copper(II) choride dihydrate / palladium dichloride / 20 °C / 15514.9 Torr / Parr bomb 4: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 60 °C 5: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide; tetrahydrofuran / 1 h 6: caesium carbonate; sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate / palladium diacetate / N,N-dimethyl-formamide; water / 1 h / 60 °C 7: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 20 °C
  • 8
  • [ 188057-35-4 ]
  • [ 1215107-73-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 0.5 h / 130 °C 2: triethylamine; copper(l) iodide / trans-bis(triphenylphosphine)palladium dichloride / 2 h / 85 °C / Inert atmosphere 3: potassium carbonate; sodium acetate; copper(II) choride dihydrate / palladium dichloride / 20 °C / 15514.9 Torr / Parr bomb 4: sodium hydroxide; water / tetrahydrofuran; methanol / 1 h / 60 °C 5: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide; tetrahydrofuran / 1 h 6: caesium carbonate; sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate / palladium diacetate / N,N-dimethyl-formamide; water / 1 h / 60 °C
  • 9
  • [ 188057-35-4 ]
  • [ 1352880-36-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 0.5 h / 130 °C 2: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3: potassium carbonate / methanol / 50 °C
Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 3 h / 50 °C / Inert atmosphere 2: copper(l) iodide; N-ethyl-N,N-diisopropylamine; potassium carbonate / 60 °C
  • 10
  • [ 188057-35-4 ]
  • [ 1066-54-2 ]
  • [ 2166485-77-2 ]
YieldReaction ConditionsOperation in experiment
67.2% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 50℃; for 3h; Inert atmosphere; 25.25f Step 25f: Preparation of 3-hydroxy-6-bromo-2-(trimethylsilylethynyl)pyridine (6-bromo-2-((trimethylsilyl)ethynyl)pyridin-3-ol) (Compound 0503-98) Under nitrogen protection,6-bromo-3-hydroxy-2-iodopyridine (0502-98) (2.0 g, 6.67 mmol, 1.0 equiv),Trimethylsilylacetylene (655 mg, 6.67 mmol, 1.0 equiv),Cuprous iodide (19 mg, 0.1 mmol, 0.015 equiv) andBistriphenylphosphine dichloropalladium (140 mg, 0.2 mmol, 0.03 equiv)Add to 30 ml of tetrahydrofuran andIn a solution of 15 ml of chloroform,Triethylamine (2.02 g, 20 mmol, 3.0 equiv) was then added dropwise.The mixture is heated to 50 °C,The reaction was stirred for 3 hours.Cool to room temperatureAfter filtration and concentration under reduced pressure, the residue was purified by silica gel column chromatography (eluent: petroleum ether:ethyl acetate=25:1) to give 3-hydroxy-6-bromo-2-(trimethylsilylacetyl). Pyridine (1.21 g, yield: 67.2%).
  • 11
  • [ 188057-35-4 ]
  • [ 220983-57-3 ]
  • [ 2245037-09-4 ]
YieldReaction ConditionsOperation in experiment
90% With di-isopropyl azodicarboxylate; triphenylphosphine In benzene at 20℃; for 4h; Schlenk technique; Inert atmosphere;
Same Skeleton Products
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