630-580-1088 sales@ambeed.com
Structure Search

List Search MOL Search Structure Search

0
Chemistry
Asymmetric Synthesis >>Chiral Building BlocksChiral Catalysts, Chiral Ligands and Chiral ReagentsChiral Resolution ReagentsCatalysis Chemistry >>Achiral Crown LigandsC-H ActivationCarbon-Donor LigandsChiral Crown LigandsCross-CouplingCross-Coupling Using Transition Metal CatalystsDACH or Trost LigandsDiketone LigandsHydrogenationChemical Biology >>Conjugation ChemistryGlycoscienceLinkers and CrosslinkersNucleic Acid ChemistryPEGylation
Peptide ChemistryPhotolabile Protecting GroupHeterocyclic Building Blocks >>Acridinium SeriesAliphatic HeterocyclesAromatic HeterocyclesAzetidinesBenzimidazolesBenzisoxazolesBenzodioxansBenzofuransBenzothiazolesInorganic reagents >>Inorganic reagentOrganic Building Blocks >>Acyl ChloridesAlcoholsAldehydesAliphatic Chain HydrocarbonsAliphatic Cyclic Hydrocarbons
AlkenylsAlkylsAlkynylsAmidesOrganometallic Reagents >>Grignard ReagentsOrganoarsenicOrganobismuthOrganoboronOrganogermaniumOrganolithiumOrganomercuryOrganosiliconOrganotinSpecialty Synthesis >>Enzyme-Mediated SynthesisFluorous SynthesisIonic LiquidsSolid Supported SynthesisStains and Dyes >>
Acid DyesAzoic DyesBasic DyesDirect DyesDisperse DyesDye IntermediatesMordant DyesOil DyesOther Stains and DyesSynthetic Reagents >>Acids and BasesC-C Bond FormationC-X Bond Formation (Halogen)C-X Bond Formation (Non-Halogen)Chelation and Complexation CompoundsCondensation AgentsCouplingDehydrating ReagentsFluorination Reagents
Pharmaceutical Intermediates
Analgesics >>BenzhydrocodoneBicifadineCapsaicinCelecoxibDebio-0827DexamethasoneElagolix SodiumEsketamine HydrochlorideIbuprofen sodiumAnesthetics >>CiprofolEsketamine HydrochlorideFospropofol Fospropofol DisodiumLevobupivacaine RemimazolamRemimazolam BesilateRemimazolam besylateRopivacaineAnti-Addiction Agents >>Kakonein
Lofexidine HydrochlorideVarenicline Anti-inflammatory Agents >>ApremilastAsunaprevirATB-346 RelatedBalsalazide BaricitinibBencycloquidium BromideBudesonideCefiderocol Sulfate TosylateCeftaroline Fosamil AcetateAntibacterials >>AFN-1252 RelatedAlatrofloxacin Bedaquiline FumarateBesifloxacin BrilacidinCaspofungin AcetateCefiderocol Sulfate TosylateCefilavancinCeftaroline Fosamil
Anticonvulsants >>BrivaracetamCannabidiolEscitalopram OxalateEslicarbazepine Acetate RelatedFosphenytoinGabapentin EnacarbilJNJ-10234094LacosamideLevetiracetam RelatedAntidementia Agents >>Azeliragon RelatedDavunetideDonepezil HydrochlorideDonepezil RelatedEnsaculinFlorbetaben Flortaucipir F 18Flutemetamol IdalopirdineAntidepressants >>4-Chlorokynurenine
AgomelatineAgomelatine RelatedAllopregnanolone RelatedAmibegronAmitifadineAripiprazole RelatedBasimglurantBefloxatoneAntiemetics >>AprepitantAprepitant RelatedDolasetron RelatedDolasetron Mesylate HydrateFosaprepitant DimeglumineFosaprepitant RelatedOlanzapinePalonosetron RelatedPalonosetron HydrochlorideAntifungals >>Anidulafungin RelatedCabotegravirMore >>
Inhibitors/Agonists
ADC >>ADC LinkerADC Linker with PayloadADC ToxinAnti-infection >>3CLproAntibacterialAntifungalAntiparasiticAntiprotozoalAntiviralBVDVCMVDengue VirusApoptosis >>Apoptosis InducerBcl-2c-Mycc-RETC/EBPCARDCaspase
DAPKIAPAutophagy >>AutophagyLC3LRRK2LysosomemitoNEETPPTSPHKTFEBULKBiochemical Reagent >>Cationic & Neutral LipidsDendrimersDye ReagentCell Cycle >>APCAurora KinaseBUBCasein KinaseCdc25
CDKChkCRM1DHFRCytoskeleton >>ActinArp2/3 ComplexCytoplasmic dyneinDynaminFAKFilamin-AGap JunctionIntegrinMicrotubule/TubulinDNA Damage >>AP endonucleaseATAD5ATM/ATRBRCADNA Alkylator/CrosslinkerDNA-PKMore >>
Material Science
Aggregation-Induced Emission >>Other AIE BlocksTetraphenylethylene SeriesElectronic Materials >>Battery MaterialsDye-Sensitized Solar Cell (DSSC) MaterialsElectronic MaterialLiquid Crystal (LC) MaterialsMolecular ConductorsOrganic Light-Emitting Diode (OLED) MaterialsOrganic Solar Cell (OPV) MaterialsOrganic Transistor (OFET) MaterialsPerovskite Solar Cell (PSC) MaterialsMagnetic Materials >>Magnetic Ionic LiquidsMagnetic MaterialMagnetic Metal Complexes Organic Radicals Material Building Blocks >>Ligands for Functional Metal ComplexesLiquid Crystal (LC) Building BlocksPhthalocyanine Building BlocksPolymer and Macromolecule Semiconductor Building BlocksSmall Molecule Semiconductor Building BlocksSolubility Enhancing Reagents
Supramolecular Host Materials Nanomaterials >>Carbon NanomaterialsCeramic MembranesDendrimersGold NanoparticlesIron Oxide NanoparticlesMaterials by ApplicationMesoporous MaterialsMetals and Metal AlloysNano Minerals: NanoclaysOptical Materials >>Coumarin DyesCyanine and Squarylium DyesDCM DyesDipyrromethene DyesFluorescence MaterialsFluorescent ProbesHeat and Pressure Sensitive DyesNear-Infrared (NIR) DyesOrganic Non-Linear Optical (NLO) MaterialsOrganic ligands for MOF materials >>Carboxylic MOF ligandsHalogen seriesMOF ligands of nitrogenous carboxylic acids
Nitrogen containing MOF ligandsOrganic frame monomer blockOther MOF ligandsPorphyrin seriesTwo dimensional MOF ligandsOrganic monomer of COF >>Aldehyde based COF monomerAlkynyl COF monomerAmino COF monomerBoric acid COF monomerCyano COF monomerMultifunctional COF monomerOther COF monomerTriphene seriesOrganic Pigments >>Organic PigmentOther Materials >>Mateial OtherPolymer Science >>MonomersPolymer AdditivesPolymerization ReagentsPolymersResins
Life Science
ADC-linkers >>ADC-linkerAmino Acids >>Amino AcidAmino Acid DerivativesAnalytical Science >>Stable IsotopesAPIs >>API
DNA/RNA >>Nucleosides and NucleotidesEnzymes >>EnzymeOther Life Science >>CRISPR/Cas9eIFIRE1Neuronal Signaling
Sigma ReceptorPeptides >>PeptideStandard Substrates >>Standard SubstrateSteroids >>Other Steroids
Contact Us
Home Cart 0 Sign in  
X
Chemistry
Organic Building Blocks
Benzene Compounds
2-Amino-5-bromo-3-methoxybenzonitrile
Chemistry
Organic Building Blocks
Benzene Compounds
Benzene Compounds

[ CAS No. 176718-54-0 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

type HazMat fee
Excepted Quantity Free
Inaccessible (Haz class 6.1), Domestic USD 41.00
Inaccessible (Haz class 6.1), International USD 64.00
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 83.00
Accessible (Haz class 3, 4, 5 or 8), International USD 133.00
3d Animation Molecule Structure of 176718-54-0
Chemical Structure| 176718-54-0
Chemical Structure| 176718-54-0
Structure of 176718-54-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 88K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 176718-54-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 176718-54-0 ]

SDS
Alternatived Products of [ 176718-54-0 ]

Product Details of [ 176718-54-0 ]

CAS No. :176718-54-0 MDL No. :MFCD22570412
Formula : C8H7BrN2O Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :227.06 g/mol Pubchem ID :-
Synonyms :

Calculated chemistry of of [ 176718-54-0 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.75
TPSA : 59.04 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) : -6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.94
Log Po/w (XLOGP3) : 2.17
Log Po/w (WLOGP) : 1.92
Log Po/w (MLOGP) : 1.25
Log Po/w (SILICOS-IT) : 1.76
Consensus Log Po/w : 1.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.92
Solubility : 0.274 mg/ml ; 0.00121 mol/l
Class : Soluble
Log S (Ali) : -3.04
Solubility : 0.206 mg/ml ; 0.000906 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.11
Solubility : 0.175 mg/ml ; 0.000773 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 176718-54-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P264-P270-P280-P301+P310+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P405-P501 UN#:3439
Hazard Statements:H301-H315-H319 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 176718-54-0 ]

* 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 [ 176718-54-0 ]

[ 176718-54-0 ] Synthesis Path-Downstream   1~24

  • 1
  • [ 148932-68-7 ]
  • [ 176718-54-0 ]
Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 11285 - 11290
    Angew. Chem.,2019,vol. 131,p. 11407 - 11412,6
[2]Chemical and Pharmaceutical Bulletin,1996,vol. 44,p. 547 - 551
  • 2
  • [ 176718-54-0 ]
  • [ 176718-55-1 ]
YieldReaction ConditionsOperation in experiment
72.6% With boron tribromide In dichloromethane Ambient temperature;
Reference： [1]Goto; Nakamura; Morioka; Kondo; Naito; Tsutsumi [Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 3, p. 547 - 551]
  • 3
  • [ 99595-85-4 ]
  • [ 176718-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 74.5 percent / SOCl2 / tetrahydrofuran / Ambient temperature 2: 87.5 percent / H2 / 10percent Pd/C / ethyl acetate / 2 h / 760 Torr 3: 78.6 percent / NBS / dimethylformamide / 1 h / Ambient temperature
Reference： [1]Goto; Nakamura; Morioka; Kondo; Naito; Tsutsumi [Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 3, p. 547 - 551]
  • 4
  • [ 4920-80-3 ]
  • [ 176718-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: SOCl2 / CH2Cl2 / 2 h / Heating 2: aq. NH3 / tetrahydrofuran / 0.5 h / Ambient temperature 3: 74.5 percent / SOCl2 / tetrahydrofuran / Ambient temperature 4: 87.5 percent / H2 / 10percent Pd/C / ethyl acetate / 2 h / 760 Torr 5: 78.6 percent / NBS / dimethylformamide / 1 h / Ambient temperature
Reference： [1]Goto; Nakamura; Morioka; Kondo; Naito; Tsutsumi [Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 3, p. 547 - 551]
  • 5
  • [ 15865-57-3 ]
  • [ 176718-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aq. NH3 / tetrahydrofuran / 0.5 h / Ambient temperature 2: 74.5 percent / SOCl2 / tetrahydrofuran / Ambient temperature 3: 87.5 percent / H2 / 10percent Pd/C / ethyl acetate / 2 h / 760 Torr 4: 78.6 percent / NBS / dimethylformamide / 1 h / Ambient temperature
Reference： [1]Goto; Nakamura; Morioka; Kondo; Naito; Tsutsumi [Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 3, p. 547 - 551]
  • 6
  • [ 142596-50-7 ]
  • [ 176718-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 87.5 percent / H2 / 10percent Pd/C / ethyl acetate / 2 h / 760 Torr 2: 78.6 percent / NBS / dimethylformamide / 1 h / Ambient temperature
Reference： [1]Goto; Nakamura; Morioka; Kondo; Naito; Tsutsumi [Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 3, p. 547 - 551]
  • 7
  • [ 176718-54-0 ]
  • sodium 2-amino-5-bromo-3-cyanophenyl sulfate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 72.6 percent / BBr3 / CH2Cl2 / Ambient temperature 2: 49.7 percent / SO3*NMe3, NaOH, NaHCO3 / H2O / 72 h / Ambient temperature
Reference： [1]Goto; Nakamura; Morioka; Kondo; Naito; Tsutsumi [Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 3, p. 547 - 551]
  • 8
  • 2-methylpropyl zinc bromide [ No CAS ]
  • [ 176718-54-0 ]
  • [ 943247-84-5 ]
YieldReaction ConditionsOperation in experiment
97% In tetrahydrofuran at 20℃; for 2h; 36 Example 36: 5-Isobutyl-7-methoxy-N-l,3-thiazol-2-yl-lH-indazol-3-amineI) NaNO2, cone. HCI2J SnCI2 [0378] To a stirred solution of 2-amino-5-bromo-3-methoxybenzonitrile (3.41 g, 15 mmol) in THF (60 mL) were added l,l'-bis(diphenylphosphino)ferrocenedichloro palladium (1.23 g, 1.5 mmol), and 2-methyIpropylzinc bromide (0.5 M in THF, 75 mL, 37.5 mmol) at room temperature under nitrogen atmosphere, and the mixture was stirred for 2 h. To the mixture was added H2O, and the insoluble material was removed by filtration and washed with EtOAc. The organic layer of the filtrate was separated, washed with H2O and brine, dried (MgSO4), filtered, and concentrated in vacuo. Purification by silica gel chromatography (hexane:EtOAc=10:l to 5:1) gave 2.977 g (97%) of 2-amino-5-isobutyl-3- methoxybenzonitrile (compound 36A) as a light yellow oil. 1H NMR (300 MHz, CDCl3) δ 0.88 (d, 6H, 7=6.82 Hz) 1.69 - 1.90 (m, IH) 2.35 (d, 2H, 7=7.19 Hz) 3.86 (s, 3H) 4.43 (brs, 2H) 6.68 (d, IH, 7=1.51 Hz) 6.76 (d, IH, 7=1.89 Hz). MS (ES) [m+H] calc'd for C12Hi6N2O, 205; found 205.[0379] 5-Isobutyl-7-methoxy-lH-indazol-3-amine (compound 36B) was prepared in 94% yield from 2-amino-5-isobutyl-3-methoxybenzonitrile according to a procedure analogous to that outlined in Example 28. 1H NMR (300 MHz, DMSO-cfe) δ 0.88 (d, 6H, 7=6.44 Hz) 1.77 - 1.95 (m, IH) 2.46 (d, 2H, 7=7.19 Hz) 3.86 (s, 3H) 5.1 1 (s, 2H) 6.54 (s, IH) 6.97 (s, IH) 11.34 (s, IH). MS (ES) [m+H] calc'd for Ci2H17N3O, 220; found 220. [0380] iV-(5-Isobutyl-7-methoxy-lH-indazol-3-yl)thiourea (compound 36C) was prepared in 96% yield from 5-isobutyl-7-methoxy-lH-indazol-3-arnine according to a procedure analogous to that outlined in Example 9. 1H NMR (300 MHz, DMSO-^6) δ 0.90 (d, 6H, 7=6.44 Hz) 1.82 - 1.97 (m, IH) 2.44 - 2.52 (m, 2H) 3.92 (s, 3H) 6.70 (s, IH) 7.52 (s, IH) 8.63 (brs, IH) 9.21 (brs, IH) 10.66 (s, IH) 12.74 (s, IH). MS (ES) [m+H] calc'd forCi3Hi8N4OS, 279; found 279. " [0381] The title compound was prepared in 47% yield from N-(5-isobutyl-7-methoxy-lH- indazol-3-yl)thiourea according to a procedure analogous to that outlined in Example 28. 1H NMR (300 MHz, DMSOd6) δ 0.90 (d, 6H, 7=6.44 Hz) 1.81 - 1.97 (m, IH) 2.49 - 2.50 (m, 2H) 3.92 (s, 3H) 6.68 (s, IH) 6.95 (d, IH, 7=3.79 Hz) 7.32 (d, IH, 7=3.79 Hz) 7.41 (s, IH) 1 1.08 (brs, IH) 12.36 (s, IH). MS (ES) [m+H] calc'd for C15H18N4OS, 303; found 303.
97% Stage #1: 2-methylpropyl zinc bromide; 2-amino-3-methoxy-5-bromobenzonitrile In tetrahydrofuran at 20℃; for 2h; Stage #2: With water In tetrahydrofuran 100 To a tetrahydrofuran solution (60 mL) of 2-amino-5-bromo- 3-methoxybenzonitrile (3.41 g) and 1,1'- bis (diphenylphosphino) ferrocenepalladium(II) dichloromethane complex (3.41 g) was added dropwise 2-methylpropylzinc bromide (0.5M tetrahydrofuran solution, 75 mL) at room temperature and the mixture was stirred for 2 hr. To the reaction mixture was added water, and the insoluble materials were filtered and washed with ethyl acetate. The organic layer in the mother liquor was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10:1 - 5:1) to give the title compound (2.97 g, yield 97%) pale-yellow oil. MS: 205 (MH+) .
Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2007/75847, 2007, A2 Location in patent: Page/Page column 124-125
[2]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/156757, 2008, A1 Location in patent: Page/Page column 161
  • 9
  • [ 176718-54-0 ]
  • [ 1093965-94-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 2 h / 20 °C 2.1: boron tribromide / dichloromethane / 20 °C / Cooling with ice 2.2: Cooling with ice
Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/156757, 2008, A1
  • 10
  • [ 176718-54-0 ]
  • [ 1093965-95-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 2 h / 20 °C 2.1: boron tribromide / dichloromethane / 20 °C / Cooling with ice 2.2: Cooling with ice 3.1: potassium carbonate / N,N-dimethyl-formamide / 50 °C
Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/156757, 2008, A1
  • 11
  • [ 176718-54-0 ]
  • [ 1093965-96-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 2 h / 20 °C 2.1: boron tribromide / dichloromethane / 20 °C / Cooling with ice 2.2: Cooling with ice 3.1: potassium carbonate / N,N-dimethyl-formamide / 50 °C 4.1: hydrogenchloride; sodium nitrite / water / 0.75 h / -2 - 0 °C 4.2: 0 - 20 °C
Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/156757, 2008, A1
  • 12
  • [ 176718-54-0 ]
  • [ 1093966-19-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran / 2 h / 20 °C 2.1: boron tribromide / dichloromethane / 20 °C / Cooling with ice 2.2: Cooling with ice 3.1: methanesulfonyl chloride; triethylamine / ethyl acetate / 1 h / Cooling with ice 3.2: 4 h / 80 °C
Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2008/156757, 2008, A1
  • 13
  • [ 176718-54-0 ]
  • C46H60N2O4Si2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 0 °C 1.2: 20 h / 0 - 20 °C 2.1: boron tribromide / toluene / 24 h / Reflux 3.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C 4.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine / 27 h / Reflux; Inert atmosphere 5.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; toluene; ethanol / 20 h / Inert atmosphere; Reflux
Reference： [1]Paintner, Tobias; Björk, Jonas; Du, Ping; Klyatskaya, Svetlana; Paszkiewicz, Mateusz; Hellwig, Raphael; Uphoff, Martin; Öner, Murat A.; Cuniberto, Edoardo; Deimel, Peter S.; Zhang, Yi-Qi; Palma, Carlos-Andres; Allegretti, Francesco; Ruben, Mario; Barth, Johannes V.; Klappenberger, Florian [Angewandte Chemie - International Edition, 2019, vol. 58, # 33, p. 11285 - 11290][Angew. Chem., 2019, vol. 131, p. 11407 - 11412]
  • 14
  • [ 176718-54-0 ]
  • C8H5BrINO [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: 2-amino-3-methoxy-5-bromobenzonitrile With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With potassium iodide In water at 0 - 20℃; for 20h;
Reference： [1]Paintner, Tobias; Björk, Jonas; Du, Ping; Klyatskaya, Svetlana; Paszkiewicz, Mateusz; Hellwig, Raphael; Uphoff, Martin; Öner, Murat A.; Cuniberto, Edoardo; Deimel, Peter S.; Zhang, Yi-Qi; Palma, Carlos-Andres; Allegretti, Francesco; Ruben, Mario; Barth, Johannes V.; Klappenberger, Florian [Angewandte Chemie - International Edition, 2019, vol. 58, # 33, p. 11285 - 11290][Angew. Chem., 2019, vol. 131, p. 11407 - 11412]
  • 15
  • [ 176718-54-0 ]
  • C7H3BrINO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 0 °C 1.2: 20 h / 0 - 20 °C 2.1: boron tribromide / toluene / 24 h / Reflux
Reference： [1]Paintner, Tobias; Björk, Jonas; Du, Ping; Klyatskaya, Svetlana; Paszkiewicz, Mateusz; Hellwig, Raphael; Uphoff, Martin; Öner, Murat A.; Cuniberto, Edoardo; Deimel, Peter S.; Zhang, Yi-Qi; Palma, Carlos-Andres; Allegretti, Francesco; Ruben, Mario; Barth, Johannes V.; Klappenberger, Florian [Angewandte Chemie - International Edition, 2019, vol. 58, # 33, p. 11285 - 11290][Angew. Chem., 2019, vol. 131, p. 11407 - 11412]
  • 16
  • [ 176718-54-0 ]
  • C9H7BrINO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 0 °C 1.2: 20 h / 0 - 20 °C 2.1: boron tribromide / toluene / 24 h / Reflux 3.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C
Reference： [1]Paintner, Tobias; Björk, Jonas; Du, Ping; Klyatskaya, Svetlana; Paszkiewicz, Mateusz; Hellwig, Raphael; Uphoff, Martin; Öner, Murat A.; Cuniberto, Edoardo; Deimel, Peter S.; Zhang, Yi-Qi; Palma, Carlos-Andres; Allegretti, Francesco; Ruben, Mario; Barth, Johannes V.; Klappenberger, Florian [Angewandte Chemie - International Edition, 2019, vol. 58, # 33, p. 11285 - 11290][Angew. Chem., 2019, vol. 131, p. 11407 - 11412]
  • 17
  • [ 176718-54-0 ]
  • C20H28BrNO2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium nitrite; hydrogenchloride / water / 0.5 h / 0 °C 1.2: 20 h / 0 - 20 °C 2.1: boron tribromide / toluene / 24 h / Reflux 3.1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 20 °C 4.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine / 27 h / Reflux; Inert atmosphere
Reference： [1]Paintner, Tobias; Björk, Jonas; Du, Ping; Klyatskaya, Svetlana; Paszkiewicz, Mateusz; Hellwig, Raphael; Uphoff, Martin; Öner, Murat A.; Cuniberto, Edoardo; Deimel, Peter S.; Zhang, Yi-Qi; Palma, Carlos-Andres; Allegretti, Francesco; Ruben, Mario; Barth, Johannes V.; Klappenberger, Florian [Angewandte Chemie - International Edition, 2019, vol. 58, # 33, p. 11285 - 11290][Angew. Chem., 2019, vol. 131, p. 11407 - 11412]
  • 18
  • [ 321-23-3 ]
  • [ 176718-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: 3 h / 60 °C 2.1: acetic acid; iron / ethanol; water / 6 h / 80 °C 3.1: sodium sulfate; hydrogenchloride / water; 1,4-dioxane / 0.17 h / 50 °C 3.2: 6 h / 80 °C 4.1: sulfuric acid / 1 h / 40 °C 5.1: sodium hydroxide; dihydrogen peroxide / 1 h / 60 °C 6.1: thionyl chloride / chloroform / 3 h / 60 °C 7.1: ammonium hydroxide / 0.5 h / 20 °C 8.1: phosphorus pentoxide / toluene / 1 h / 110 °C
Reference： [1]Current Patent Assignee: WUXI SHUANGQI TECH - CN112300028, 2021, A
  • 19
  • [ 103966-66-1 ]
  • [ 176718-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: acetic acid; iron / ethanol; water / 6 h / 80 °C 2.1: sodium sulfate; hydrogenchloride / water; 1,4-dioxane / 0.17 h / 50 °C 2.2: 6 h / 80 °C 3.1: sulfuric acid / 1 h / 40 °C 4.1: sodium hydroxide; dihydrogen peroxide / 1 h / 60 °C 5.1: thionyl chloride / chloroform / 3 h / 60 °C 6.1: ammonium hydroxide / 0.5 h / 20 °C 7.1: phosphorus pentoxide / toluene / 1 h / 110 °C
Reference： [1]Current Patent Assignee: WUXI SHUANGQI TECH - CN112300028, 2021, A
  • 20
  • [ 59557-91-4 ]
  • [ 176718-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium sulfate; hydrogenchloride / water; 1,4-dioxane / 0.17 h / 50 °C 1.2: 6 h / 80 °C 2.1: sulfuric acid / 1 h / 40 °C 3.1: sodium hydroxide; dihydrogen peroxide / 1 h / 60 °C 4.1: thionyl chloride / chloroform / 3 h / 60 °C 5.1: ammonium hydroxide / 0.5 h / 20 °C 6.1: phosphorus pentoxide / toluene / 1 h / 110 °C
Reference： [1]Current Patent Assignee: WUXI SHUANGQI TECH - CN112300028, 2021, A
  • 21
  • N-(4-bromo-2-methoxyphenyl)-2-(hydroxyimino)acetamide [ No CAS ]
  • [ 176718-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfuric acid / 1 h / 40 °C 2: sodium hydroxide; dihydrogen peroxide / 1 h / 60 °C 3: thionyl chloride / chloroform / 3 h / 60 °C 4: ammonium hydroxide / 0.5 h / 20 °C 5: phosphorus pentoxide / toluene / 1 h / 110 °C
Reference： [1]Current Patent Assignee: WUXI SHUANGQI TECH - CN112300028, 2021, A
  • 22
  • 5-bromo-7-methoxyindoline-2,3-dione [ No CAS ]
  • [ 176718-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium hydroxide; dihydrogen peroxide / 1 h / 60 °C 2: thionyl chloride / chloroform / 3 h / 60 °C 3: ammonium hydroxide / 0.5 h / 20 °C 4: phosphorus pentoxide / toluene / 1 h / 110 °C
Reference： [1]Current Patent Assignee: WUXI SHUANGQI TECH - CN112300028, 2021, A
  • 23
  • [ 864293-44-7 ]
  • [ 176718-54-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / chloroform / 3 h / 60 °C 2: ammonium hydroxide / 0.5 h / 20 °C 3: phosphorus pentoxide / toluene / 1 h / 110 °C
Reference： [1]Current Patent Assignee: WUXI SHUANGQI TECH - CN112300028, 2021, A
  • 24
  • [ 1227361-07-0 ]
  • [ 176718-54-0 ]
YieldReaction ConditionsOperation in experiment
93.1% With phosphorus pentoxide In toluene at 110℃; for 1h; 1.8; 2.8; 3.8 (4) Synthesis of compound I Add 80g (326.5mmol) of compound IX, 400ml of toluene, 232g (1632.5mmol) of phosphorus pentoxide into the reaction flask, heat at 110°C and reflux for 1h, and follow the reaction by HPLC until the reaction of compound IX is complete; quench into 400ml of ice water and separate into layers , The organic phase was concentrated to dryness, methanol beating, the solid was filtered, and dried to obtain 69 g of compound I. The molar yield was 93.1%.
Reference： [1]Current Patent Assignee: WUXI SHUANGQI TECH - CN112300028, 2021, A Location in patent: Paragraph 0032; 0048-0051; 0052; 0068-0069; 0070; 0086-0087

Tags: 176718-54-0 synthesis path| 176718-54-0 SDS| 176718-54-0 COA| 176718-54-0 purity| 176718-54-0 application| 176718-54-0 NMR| 176718-54-0 COA| 176718-54-0 structure

Related Products
Historical Records