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CAS No. : | 60770-67-4 | MDL No. : | MFCD12406296 |
Formula : | C8H5IO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LNRVLSJOGUTLDU-UHFFFAOYSA-N |
M.W : | 244.03 | Pubchem ID : | 10083161 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 48.93 |
TPSA : | 13.14 Ų |
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) : | -5.68 cm/s |
Log Po/w (iLOGP) : | 2.26 |
Log Po/w (XLOGP3) : | 2.97 |
Log Po/w (WLOGP) : | 3.04 |
Log Po/w (MLOGP) : | 2.46 |
Log Po/w (SILICOS-IT) : | 3.41 |
Consensus Log Po/w : | 2.83 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.89 |
Solubility : | 0.0314 mg/ml ; 0.000129 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.91 |
Solubility : | 0.301 mg/ml ; 0.00123 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.24 |
Solubility : | 0.0139 mg/ml ; 0.0000571 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.9 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Entspr. 3-Hydroxy-2,3-dihydroverb. (IVl), HCl/EtOH, Δ; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With sodium t-butanolate In N,N-dimethyl-formamide at 110℃; for 24h; | 7.a Step 7a. 2-(Benzofuran-5-ylthio)-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-4-amine (Compound 0205-10) A mixture of compound 0204 (1.0 g, 3.5 mmol), 5-iodobenzofuran (1.2 g, 4.92 mmol), neocuproine hydrate (73 mg, 0.35 mmol), CuI (67 mg, 0.35 mmol) and NaO-t-Bu (403 mg, 4.2 mmol) in anhydrous DMF (20 mL) was stirred for 24 h at 110° C. (oil bath) under nitrogen atmosphere. The solvent was removed under high vacuum and the crude purified by column chromatography on silica gel (CH2Cl2/MeOH=50/1) to give the title compound 0205-10 as a yellow solid (0.44 g, 31%): LCMS: 403 [M+1]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 25℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: catacxium A; 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; palladium diacetate / isopropyl alcohol / 16 h / 75 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: N,N-dimethyl-formamide / 20 °C / Inert atmosphere; Schlenk technique |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; palladium diacetate; catacxium A In isopropyl alcohol at 75℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In toluene at 50℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With potassium phosphate; copper(l) iodide; N-(2-phenylphenyl)-N′-benzyl oxalamide In acetonitrile at 90℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 3-Fluoropyridine; bis(acetylacetonate)nickel(II); lithium chloride; magnesium chloride; zinc In N,N-dimethyl-formamide at 25℃; for 12h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 16 h / 20 °C / Inert atmosphere 2: trifluorormethanesulfonic acid; tetrabutylammomium bromide / chloroform / 1 h / 0 °C / Molecular sieve; Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / 16 h / 20 °C / Inert atmosphere 2: trifluorormethanesulfonic acid; tetrabutylammomium bromide / chloroform / 1 h / 0 °C / Molecular sieve; Inert atmosphere; Sealed tube 3: bis(trifluoromethanesulfonyl)amide; 1,1,1,3',3',3'-hexafluoro-propanol; water / 0.12 h / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With pyridine; nickel(II) iodide; 4,5-dihydro-2-(pyridin-2-yl)-1H-imidazole; magnesium chloride; zinc In N,N-dimethyl acetamide at 20℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With (1,2-dimethoxyethane)dichloronickel(II); 4,4'-Dimethoxy-2,2'-bipyridin; magnesium bromide; zinc In N,N-dimethyl acetamide at 40℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With bis(acetylacetonate)nickel(II); 4,4'-Dimethoxy-2,2'-bipyridin; magnesium bromide; zinc In N,N-dimethyl acetamide at 40℃; for 12h; Schlenk technique; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With polyphosphoric acid In toluene for 12h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 24 h / Reflux; Inert atmosphere 2: polyphosphoric acid / toluene / 12 h / Reflux; Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With potassium fluoride; palladium diacetate; copper(II) bis(trifluoromethanesulfonate) Schlenk technique; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With copper nitrate hemi(pentahydrate); 4,4'-bis(carbomethoxy)-2,2'-bipyridine; sodium amide; In N,N-dimethyl-formamide; at 130℃; for 20h; | General procedure: Under air atmosphere, a reaction tube was charged with aryl iodides (0.5 mmol), Ph3P+CF2CO2- (268 mg, 0.75 mmol, 1.5equiv), L4 (6.3 mg, 5 mol %), Cu (NO3)2·2.5H2O (143 mg, 0.65 mmol, 1.3 equiv), NaNH2 (39 mg, 1.0 mmol, 2.0 equiv) and dry DMF (4 mL). The resulting mixture was stirred at 130C for 15 h. After being cooled to room temperature, the mixture was filtered through a pad of Celite. The solid was washed with DCM, and the combined organic phase was washed with water (15 mL × 3). The organic layer was further washed with saturated sodium sulfite and saturated brine, and then dried with sodium sulfate. After the solvent was removed by concentration under vacuum, the residue was subjected to flash column chromatography to afford the final product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 1,2-dimethoxyethane / 12 h / 70 °C / Inert atmosphere; Schlenk technique 2: tributylphosphine / dichloromethane / 2 h / 40 °C / Inert atmosphere; Schlenk technique; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; potassium carbonate In 1,2-dimethoxyethane at 70℃; for 12h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With 2,2':6,2''-terpyridine; tris-(dibenzylideneacetone)dipalladium(0); potassium <i>tert</i>-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With dimethylsulfide borane complex; (6,6’-dimethyl-2,2'-bipyridine)nickel(II) dibromide; lithium methanolate In N,N-dimethyl acetamide at -19℃; for 12h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With copper(l) iodide; potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate; copper(l) iodide / 1-methyl-pyrrolidin-2-one / 16 h / 100 °C / Inert atmosphere 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate; copper(l) iodide / 1-methyl-pyrrolidin-2-one / 16 h / 100 °C / Inert atmosphere 2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C / Inert atmosphere; Cooling with ice 3: bis(1,5-cyclooctadiene)nickel (0); C15H24N2*H(1+)*BF4(1-); sodium t-butanolate / 1,4-dioxane / 20 h / 110 °C / Inert atmosphere; Glovebox |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With tris-(dibenzylideneacetone)dipalladium(0); 1-iodo-butane; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; chloro-N,N,N',N'-bis(tetramethylene)formamidinium hexafluorophosphate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 120℃; for 16h; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide for 16h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 16 h / Inert atmosphere; Schlenk technique 2: tris(pentafluorophenyl)borate; 4,6,6-trichloro-1-methylbicyclo[3.1.0]hexane / chlorobenzene / 110 h / 140 °C / Glovebox; Inert atmosphere; Schlenk technique |