Home Cart 0 Sign in  
X

[ CAS No. 5145-71-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 5145-71-1
Chemical Structure| 5145-71-1
Chemical Structure| 5145-71-1
Structure of 5145-71-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 5145-71-1 ]

Related Doc. of [ 5145-71-1 ]

Alternatived Products of [ 5145-71-1 ]

Product Details of [ 5145-71-1 ]

CAS No. :5145-71-1 MDL No. :MFCD00128350
Formula : C11H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :WYFMHHMFUMBCGI-UHFFFAOYSA-N
M.W : 173.21 Pubchem ID :272427
Synonyms :

Calculated chemistry of [ 5145-71-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 11
Fraction Csp3 : 0.09
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.26
TPSA : 14.16 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.5
Log Po/w (XLOGP3) : 3.05
Log Po/w (WLOGP) : 2.49
Log Po/w (MLOGP) : 1.78
Log Po/w (SILICOS-IT) : 2.04
Consensus Log Po/w : 2.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.33
Solubility : 0.0811 mg/ml ; 0.000468 mol/l
Class : Soluble
Log S (Ali) : -3.01
Solubility : 0.168 mg/ml ; 0.000969 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.42
Solubility : 0.0656 mg/ml ; 0.000378 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.24

Safety of [ 5145-71-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5145-71-1 ]

* 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 [ 5145-71-1 ]

[ 5145-71-1 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 696-59-3 ]
  • [ 104-94-9 ]
  • [ 5145-71-1 ]
YieldReaction ConditionsOperation in experiment
98% With magnesium iodide etherate; In acetonitrile; at 80℃; for 2h; General procedure: A Schlenk reaction tube was charged with primary aromatic amine (5.0 mmol), 2,5-dimethoxytetrahydrofuran (6.0 mmol), MgI2 etherate (10percent mmol), and acetonitrile (10 mL). The reaction mixture was stirred at 80 °C for several hours and then concentrated in vacuo. The residue was purified by flash column chromatography on a silica gel to give the desired product.
96% With ionic liquid immobilized on gamma-Fe2O3(at)SiO2 nanoparticles; In water; at 100℃; for 0.5h; General procedure: To a solution of amine (1 mmol) in water (2 ml) was added tetrahydro-2,5-dimethoxyfuran (1.1 mmol) and gamma-Fe2O3(at)SiO2?Sb-IL (0.08 g). The reaction mixture was stirred at 100 °C for a certain period of time as required to complete the reaction. During that time, the reaction was monitored constantly by TLC. After completion of the reaction, the catalyst was removed by using a magnet and washed with ethyl acetate. The aqueous solution was extracted by ethyl acetate (3 × 5 ml). The combined organic phase was dehydrated with anhydrous sodium sulfate. After the evaporation of the solvent, the residue was purified by silica gel flash chromatography using petroleum ether/ethyl acetate as the eluent to afford the pure product.
95% With bismuth (III) nitrate pentahydrate; at 20℃; for 0.0833333h;Sonication; Neat (no solvent); General procedure: Amine 2 (1.0 mmol), 2,5-dimethoxytetrahydrofuran (1, 1.2 mmol) and bismuth nitrate pentahydrate (24 mg, 5 molpercent) was irradiated in a B5510-DTH (Branson ultrasonic cleaner; Model-5510, frequency 42 kHz with an output power 135 Watts), as specified in Table 2. After completion of the reaction (monitored by TLC) diethyl ether (10 mL) was added to the reaction mixture and filtered. Pure product was isolated from the reaction mixture after evaporation of ether.
95% With L-(+)-tartaric acid-choline chloride based deep eutectic solvent; at 90℃; for 0.5h;Green chemistry; General procedure: Amine (1 mmol), 2,5-dimethoxytetrahydrofuran (1.1 mmol)and L-(+)-tartaric acid?choline chloride based DES (1.5 g) were added to a 50 mL round bottom flask and the reaction mixturewas stirred at 90 °C. The progress of the reaction was monitoredby TLC. After completion of the reaction, the mixture was cooled to room temperature and the product was extracted with ethyl acetate.After the evaporation of the solvent, the residue was purified by columnchromatography on silica gel to afford the pure product. The DES wasdried under vacuumand reused for the next cycle.
93% With bismuth (III) nitrate pentahydrate; at 90℃; for 0.166667h;Microwave irradiation; A mixture of 4-methoxyaniline (2.50 g, 20 mmol), 2,5-dimethoxytetrahydrofuran(3.20 g, 24 mmol) and bismuth(III) nitrate pentahydrate (0.6 g ) was placed in a three-necked flask in a microwave oven equipped with a temperature sensor and a reflux condenser. Then the mixture was irradiated for 10 min (300W) at 90 oC. After completion of the reaction, the mixture was cooled and extracted with diethyl ether (3 × 50 mL). The combined organic layers were driedwith anhydrous magnesium sulfate. The solvent was removed and the crude product was purified by column chromatography on silica gelusing petroleum ether and acetone (10:1, v/v) as the eluent to give the pure product 1-(4-methoxyphenyl)pyrrole (3.20 g, 93percent yield): m.p.108?112°C (lit.37 104?108 °C).
76% With Oxone; In acetonitrile; at 110℃; for 0.3h;Microwave irradiation; General procedure: Oxone (0.09 g, 0.30 mmol) was added to a solution of the aromatic primary amines (2.5 mmol) and 2,5-dimethoxytetrahydrofuron (3.0 mmol) in a solvent (5 mL) was further added (Scheme1). The reaction mixture was heated under microwave irradiation for 10 min at 110 ± 10 °C. The reaction mixture was irradiated until total consumption of the amine was verified by TLC. Water was added and the products were extracted with EtOAc (3x20 mL). The organic phasewas dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. The product was purified on a silica gel column chromatography eluted with mixture of ethylacetate/hexane (1:4) to afford the product.
74% With silica sulfuric acid; In neat (no solvent, solid phase);Milling; Green chemistry; General procedure: To the mixture of SSA catalyst (125 mg) with silica gel (875 mg), 2,5-dimethoxy-tetrahydrofuran (DMTHF) (2 mmol) and a primary amine (2 mmol) (for compound 10, 5 : 1 mmol) were added. The mixture was grinded in a glass mortar with a pestle for 5-15 min. Progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was dissolved in diethyl ether, then filtrated. The filtrate solvent was evaporated under vacuum. Thus obtained the corresponding crude product was purified by column chromatography on silica gel with n-hexane and ethyl acetate as eluents.

  • 2
  • [ 5145-71-1 ]
  • [ 670-54-2 ]
  • [ 20484-62-2 ]
  • 3
  • [ 5145-71-1 ]
  • 1-(4-Methoxy-phenyl)-1H-pyrrole; compound with iodine [ No CAS ]
  • 4
  • [ 5145-71-1 ]
  • [ 118-75-2 ]
  • [ 20484-57-5 ]
  • 5
  • [ 20484-62-2 ]
  • [ 5145-71-1 ]
  • [ 670-54-2 ]
  • 6
  • [ 20484-57-5 ]
  • [ 5145-71-1 ]
  • [ 118-75-2 ]
  • 8
  • [ 5145-71-1 ]
  • [ 762-42-5 ]
  • [ 74986-20-2 ]
  • 9
  • [ 5145-71-1 ]
  • [ 762-42-5 ]
  • [ 74986-13-3 ]
  • [ 74986-01-9 ]
  • 10
  • [ 5145-71-1 ]
  • [ 407-25-0 ]
  • 1-p-methoxyphenyl-2-trifluoroacetylpyrrole [ No CAS ]
  • 11
  • [ 5145-71-1 ]
  • [ 1972-28-7 ]
  • [ 73018-06-1 ]
  • 12
  • [ 5145-71-1 ]
  • [ 1460-08-8 ]
  • 3-Hydroxy-2-<N-(4-methoxyphenyl)pyrrol-3-yl>cyclohex-2-enone [ No CAS ]
  • 14
  • [ 5145-71-1 ]
  • [ 79-37-8 ]
  • [1-(4-Methoxy-phenyl)-1H-pyrrol-2-yl]-oxo-acetyl chloride [ No CAS ]
  • 15
  • [ 5145-71-1 ]
  • [ 118-92-3 ]
  • 1,4-dihydro-1,4-(p-methoxyphenylimino)naphthalene [ No CAS ]
  • 16
  • [ 696-59-3 ]
  • [ 104-94-9 ]
  • [ 5145-71-1 ]
  • [ 54660-04-7 ]
  • 17
  • [ 50-00-0 ]
  • [ 22774-66-9 ]
  • [ 5145-71-1 ]
  • 18
  • [ 272448-30-3 ]
  • [ 5145-71-1 ]
  • (E)-4-[(E)-4-Methoxy-phenylimino]-but-2-enal [ No CAS ]
  • C18H18N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With copper diacetate; potassium carbonate; In dimethyl sulfoxide; at 105℃; for 7h; General procedure: The 128 mu L (1.0mmol) 3-iodo toluene, 208 mu L (1.5mmol) pyrrole, 125 mg calcium base montmorillonite clay, 0.0200g (0.1mmol) copper acetate, 0.2746g (2.0mmol) potassium carbonate by adding 5 ml of dimethyl sulfoxide, 105 °C reaction 7 hours, the reaction is stopped, the centrifugal separation, the separating medium is added to 15 ml distilled water, with 10 ml ethyl acetate extraction three times, combined with the phase, drying with anhydrous magnesium sulfate, the solvent is removed, with petroleum ether with ethyl acetate the volume ratio of 1:50 flow at the mixed liquid chromatographic separation, to obtain yellow oily liquid N-(3-methyl phenyl) pyrrole, its yield is 92percent.
  • 21
  • [ 5145-71-1 ]
  • [ 124-38-9 ]
  • 1-(3-carboxy-4-methoxyphenyl)pyrrole [ No CAS ]
  • 22
  • [ 5145-71-1 ]
  • [ 124-38-9 ]
  • 1-(2-Carboxy-4-methoxyphenyl)pyrrole-2-carboxylic acid [ No CAS ]
  • 23
  • [ 109-97-7 ]
  • [ 696-62-8 ]
  • [ 5145-71-1 ]
YieldReaction ConditionsOperation in experiment
95% With copper phthalocyanine; sodium hydroxide; In dimethyl sulfoxide; at 100℃; General procedure: In a 50mL RB, N-H heterocycles (1.0mmol), aryl halide (1mmol), Cu(II)Pc (0.01mmol), NaOH (1.5mmol) and DMSO (2mL) was added. This reaction mixture was stirred to a preheated oil bath at 100C for 8-12h. After completion of the reaction, it was cooled to room temperature and 20mL ethyl acetate was added. It was filtered; solid catalyst was separated and washed with 2×5mL ethyl acetate. The washing and filtrate were combined and washed with water. Ethyl acetate was removed under reduced pressure and product was purified with column chromatography.
94% With copper(II) acetate monohydrate; caesium carbonate; In N,N-dimethyl-formamide; at 110℃; for 24h;Inert atmosphere; General procedure: To a solution of Cu(OAc)2·H2O (0.01 mmol) in DMF (2 mL) were added aryl iodide (1.2 mmol), nitrogen-containing heterocycle (1.0 mmol), and Cs2CO3 (2 mmol) under nitrogen atmosphere. The mixture was stirred at 110 C for 24 h. After cooling to ambient temperature, the mixture was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel.
93% With copper(I) oxide; 1-(2-methylhydrazine-1-carbonyl)isoquinoline 2-oxide; tetrabutylammomium bromide; sodium hydroxide; In ethanol; water; at 120℃; for 12h;Schlenk technique; General procedure: A 25 mL Schlenk tube was charged with Cu2O (0.05 mmol), ArX (0.5 mmol), NHR1R2 (0.75 mmol), NaOH (1 mmol), TBAB (0.1 mmol), L2 (0.1 mmol) and H2O/EtOH (1 mL, 1/1, v/v). The mixture was stirred at 120 C for 12 h. The reaction mixture was extracted with ethyl acetate (3 10 mL), washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel(ethyl acetate/petroleum ether as the eluent) to provide the target products 3a-3w and 6.
84% With copper(ll) sulfate pentahydrate; sodium hydroxide; In dimethyl sulfoxide; at 110℃; for 12h;Sealed tube; General procedure: CuSO4·5H2O (12.50 mg, 0.05 mmol), the aryl iodide or bromide(1.0 mmol), pyrrole (1.5 mmol), NaOH (80 mg, 2 mmol), and DMSO(2 mL) were placed in a 10 mL sealed tube. The mixture was heatedat 110 C in a preheated oil bath for 12 h. It was then cooled to roomtemperature, diluted with 20 mL H2O, and the mixture was extractedwith ethyl acetate (3 × 20 mL). The combined organic phases waswashed with water and brine, dried over anhydrous Na2SO4, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel (ethyl acetate/petroleum ether, 1 : 100)to afford the target products. All C-N coupling products reported hereare known products and were characterised by GC-MS and 1H NMR,which were compared with the previously reported dates.
75% With copper(I) oxide; caesium carbonate; N-phenyl-2-pyridincarboxamide-1-oxide; In dimethyl sulfoxide; at 120℃; for 20h;Inert atmosphere; General procedure: In 50 mL round bottom flask, aryl halide (1.0 mmol), pyrazole (1.2 mmol), ligand (0.04 mmol), Cu2O (0.10 mmol), cesium carbonate (2.0 mmol), and dry solvent (20 mL) were placed under nitrogen atmosphere. The reaction mixture was heated in oil bath up to specified temperature under constant stirring for 20 h and then allowed to cool to room temperature. The reaction mixture was filtered through a plug of Celite in a fritted filter funnel and washed with ethyl acetate. If DMSO is used as solvent, it is extracted by washing the filtrate with 25 mL water for three times. The organic phase was dried over anhydrous MgSO4 and was removed under reduced pressure to provide the crude product which was purified by column chromatography on silica gel, using hexane and ethyl acetate in 3:1 ratio, respectively, as an eluent.
74% With 2-(2-tert-butylhydrazinecarbonyl)pyridine-1-oxide; tetrabutylammomium bromide; copper; potassium hydroxide; In water; at 120℃; for 12h;Sealed tube; Green chemistry; Cu (0.05 mmol), L4 (0.1 mmol), aryl halides(0.5 mmol), imidazoles (0.75 mmol), KOH (1 mmol), TBAB (0.15 mol), and H2O(1 mL) were added to a 10 mL sealed tube. The reaction mixture was reacted at120 C in a pre-heated oil bath for 12 h. The reaction mixture was cooled to room temperature, diluted with 10 mL H2O, and then the mixture was extracted with ethyl acetate (3 20 mL). The combined organic phases were washed withwater and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel (ethyl acetate/petroleum ether, 2:1 to pure ethyl acetate) to afford the target products.
73% With caesium carbonate; at 135℃; for 4h; General procedure: A mixture of pyrrole (3 ml), Cs2CO3 (1.96 g, 6 mmol), Cu0/4A or Cu2+/4A (0.3 g) and the appropriate aryl halide (3 mmol) were stirred at 135 C (bath temperature) for 4-36 h. Before adding to the mixture, Cu2+/4A was preheated at ca. 150 C for 1 h. The mixture was filtered, the solid was washed with dichloromethane. The filtrate was extracted with deionised water (2 x 40 ml). The organic phase was dried over Na2SO4 and concentrated in vacuum. The residue was distilled and clarified. Certain products (3c, 3f) were purified by recrystallization from MeOH.
63% With copper(II) acetate monohydrate; caesium carbonate; In N,N-dimethyl-formamide; at 20 - 110℃; for 24h;Inert atmosphere; Schlenk technique; General procedure: An oven-dried Schlenk tube was charged with Cu(OAc)2·H2O (0.1 mmol, 0.01 equiv), Cs2CO3(20 mmol, 2 equiv), and aryl iodide (if solid, 12 mmol, 1.2 equiv). The tube was degassed with argon for three times. Then DMF (20 mL), pyrrole (10 mmol, 1 equiv), and aryl iodide (if liquid,12 mmol, 1.2 equiv) were added via syringe under room temperature. The mixture was stirred at110 C for 24 h, and then cooled down to room temperature. The reaction mixture was quenched with water (40 mL) and extracted with ethyl ether (20 mL) for three times. The combined organic layers were dried with Na2SO4, filtered and concentrated. The crude products were purified using flash column chromatography on silica gel to afford the desired product.
46% With copper; caesium carbonate; In acetonitrile; for 72h;Inert atmosphere; Reflux; General procedure: To azole (6.0 mmol) and aryl halide (4.0 mmol) in acetonitrile (20 mL) were successively added Cu (50 mg, 0.80 mmol), Cs2CO3 (2.6 g, 8.0 mmol) and, in the case of aryl bromides, KI (99 mg, 6.0 mmol). The mixture was stirred under argon at acetonitrile reflux temperature (the reaction time is given in the product description) before dilution with AcOEt (40 mL) and filtration. Concentration under reduced pressure and purification by chromatography on silica gel (the eluent is given in the product description) led to the expected compounds.
44% With copper(I) oxide; potassium phosphate; tetrabutylammomium bromide; In water; at 130℃; for 24h;Closed system; General procedure for N-arylation of amines:The N-nucleophile (1.47 mmol), Cu2O (Sigma-Aldrich, 99.99% purity, 0.147 mmol), K3PO4 (2.94 mmol), the aryl halide (1.76 mmol), phase transfer catalyst (0.147 mmol) and water (0.75 mL) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 130 C for 24 h, then the heterogeneous mixture was cooled to RT and diluted with dichloromethane. The resulting solution was directly filtered through a pad of Celite. The combined organic extracts were dried with anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude product was purified by silica-gel column chromatography to afford the N-arylated product. The identity and purity of all products was confirmed by 1H and 13C NMR spectroscopic analysis.

Reference: [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 4101 - 4114
[2]Organic and Biomolecular Chemistry,2016,vol. 14,p. 10861 - 10865
[3]Tetrahedron Letters,2017,vol. 58,p. 3044 - 3048
[4]Tetrahedron,2011,vol. 67,p. 5282 - 5288
[5]Journal of Organic Chemistry,2007,vol. 72,p. 8943 - 8946
[6]Advanced Synthesis and Catalysis,2008,vol. 350,p. 1253 - 1257
[7]Tetrahedron,2019,vol. 75,p. 3788 - 3792
[8]Journal of the Chinese Chemical Society,2012,vol. 59,p. 480 - 484
[9]Journal of Organic Chemistry,2018,vol. 83,p. 6408 - 6422
[10]Chemical Communications,2019,vol. 55,p. 3805 - 3808
[11]Applied Organometallic Chemistry,2017,vol. 31
[12]Journal of Heterocyclic Chemistry,2008,vol. 45,p. 1815 - 1818
[13]Chinese Journal of Chemistry,2012,vol. 30,p. 875 - 880
[14]Synlett,2004,p. 128 - 130
[15]Journal of Organic Chemistry,2005,vol. 70,p. 5164 - 5173
[16]Tetrahedron Letters,2007,vol. 48,p. 245 - 248
[17]Journal of Chemical Research,2014,vol. 38,p. 180 - 182
[18]Tetrahedron Letters,2016,vol. 57,p. 2197 - 2200
[19]Tetrahedron Letters,2014,vol. 55,p. 3249 - 3251
[20]Catalysis Letters,2015,vol. 145,p. 1113 - 1119
[21]European Journal of Organic Chemistry,2011,p. 3353 - 3360
[22]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 354 - 363
[23]European Journal of Organic Chemistry,2010,p. 3621 - 3630
[24]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 1475 - 1485
[25]Tetrahedron Letters,2011,vol. 52,p. 1161 - 1164
[26]Chemistry - A European Journal,2015,vol. 21,p. 8047 - 8051
[27]Chemistry - A European Journal,2016,vol. 22,p. 4400 - 4404
[28]Organic Letters,2004,vol. 6,p. 2405 - 2408
[29]Chemistry - A European Journal,2016,vol. 22,p. 783 - 801
[30]Patent: CN109456205,2019,A .Location in patent: Paragraph 0055; 0056; 0057; 0058
  • 24
  • [ 5145-71-1 ]
  • [ 55962-05-5 ]
  • 3,4-di(toluene-p-sulfonamido)-1-(4-methoxyphenyl)pyrrole [ No CAS ]
  • 25
  • [ 109-97-7 ]
  • [ 104-92-7 ]
  • [ 5145-71-1 ]
YieldReaction ConditionsOperation in experiment
95% With caesium carbonate; at 135℃; for 24h; General procedure: A mixture of pyrrole (3 ml), Cs2CO3 (1.96 g, 6 mmol), Cu0/4A or Cu2+/4A (0.3 g) and the appropriate aryl halide (3 mmol) were stirred at 135 C (bath temperature) for 4-36 h. Before adding to the mixture, Cu2+/4A was preheated at ca. 150 C for 1 h. The mixture was filtered, the solid was washed with dichloromethane. The filtrate was extracted with deionised water (2 x 40 ml). The organic phase was dried over Na2SO4 and concentrated in vacuum. The residue was distilled and clarified. Certain products (3c, 3f) were purified by recrystallization from MeOH.
71% With copper(II) ferrite; potassium tert-butylate; In N,N-dimethyl-formamide; at 155℃; for 24h;Inert atmosphere; General procedure: To a solution of N-heterocycle (1 equiv), bromobenzene (1.02 equiv) and tBuOK (2 equiv) in dry DMF, CuFe2O4 (10 mol %) was added and heated at reflux for 24 h under N2 atmosphere. After cooling to room temperature, the mixture was diluted with ethyl acetate and the catalyst was separated by a magnetic separator. The catalyst was washed with ethyl acetate. The combined ethyl acetate layer was washed with water (twice), dried over anhydrous Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel column chromatography using petroleum ether/ethyl acetate to yield N-arylated product.
57% With 2-phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanol; copper(II) acetate monohydrate; sodium t-butanolate; In N,N-dimethyl-formamide; at 120℃; for 3h; General procedure: A mixture of N-unsubstituted compound 2 (1.0 mmol), aryl halide 1 (1.2 mmol), and t-BuONa (1.2 mmol) was stirred in DMF (0.3 mL) inthe presence of Cu(OAc)2·H2O (1 mol%) and 2-phenyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanol (1 mol%) at 120 C for the time given inTable 2. The mixture was washed with EtOAc; after removal of thesolvent, the residue was purified by column chromatography (silicagel, petroleum ether-EtOAc).
With copper(l) iodide; caesium carbonate; In N,N-dimethyl-formamide; at 120℃; for 24h;Schlenk technique; Inert atmosphere; General procedure: A flame-dried Schlenk test tube with a magnetic stirring bar was charged with CuI (0.038 mg, 0.0002 mol), Cs2CO3 (0.65 g, 0.002 mol), heterocycle (0.0014mol), 1-bromo-4-methoxybenzene (0.185 g, 0.001 mol) and DMF (10 mL) under N2. A rubber septum was replaced with a glass stopper, and the system was then evacuated twice and back filled with N2. After being stirred at 120 C for 24 h, the reaction mixture was diluted with 2-3 mL of ethyl acetate, filtered through a plug of silica gel, and washed with 30-50 mL of ethyl acetate. The filtrate was concentrated and the resulting residue was purified by column chromatography on silica gel to provide the desired product. A solution of BBr3 (0.23 mL, 0.0025mol) in CH2Cl2 (5 mL) was added dropwise to the solution of 1-(4-methoxyphenyl)-1H-heterocycle (0.001 mol) in CH2Cl2 (10 mL) cooled to 0 C. The resulting solution was stirred for 4 h at room temperature. And the solution was washed by NaHCO3, NH4Cl, NaCl solution in sequence. The CH2Cl2 was dried over anhydrous sodium sulfate, removed under vacuum, and the residue was purified by chromatography on silica gel to yield the 4-(1H-heterocycle -1-yl)phenol.4-(1H-heterocycle -1-yl)phenol (0.001 mol), N,N?-dicyclohexyl carbodiimide (DCC) (0.0012 mol), 4-dimethylaminopyridine (DMAP) (0.0002 mol) in 10 mL chloroform were placed in a Pyrex glass tube, sealed and heated at 80 C for 12 h. After cooling to room temperature, the white solid was filtrated off, and the solvent was removed under vacuum. The crude product was purified by chromatography on silica gel with to gain the desired products.

  • 26
  • [ 18276-53-4 ]
  • [ 104-92-7 ]
  • [ 5145-71-1 ]
YieldReaction ConditionsOperation in experiment
30% With caesium carbonate;palladium diacetate; 2-(di-tert-butylphosphino)-2'-isopropylbiphenyl; In carbon dioxide; at 100℃; under 39304.3 - 93089.1 Torr; for 17h;Heating in sealed cell;Product distribution / selectivity; Example 2; The reaction was carried out as described in the general method, with the R group and either the N-trimethylsilyl-pyrrole or indole as shown in Table 3, with the yields expressed in percent. The reactions were carried out at ca. 1800 psi for 17 hours. The catalyst ligand used was either: wherein ligand A is that described in the general method.
7% With caesium carbonate;palladium diacetate; johnphos; In carbon dioxide; at 100℃; under 39304.3 - 93089.1 Torr; for 17h;Heating in sealed cell;Product distribution / selectivity; Example 2; The reaction was carried out as described in the general method, with the R group and either the N-trimethylsilyl-pyrrole or indole as shown in Table 3, with the yields expressed in percent. The reactions were carried out at ca. 1800 psi for 17 hours. The catalyst ligand used was either: wherein ligand A is that described in the general method.
  • 27
  • [ 870194-13-1 ]
  • [ 104-92-7 ]
  • [ 5145-71-1 ]
  • 28
  • [ 5145-71-1 ]
  • [ 143-33-9 ]
  • [ 39779-30-1 ]
  • 30
  • [ 109-97-7 ]
  • [ 104-94-9 ]
  • [ 5145-71-1 ]
  • 31
  • [ 5145-71-1 ]
  • N-Benzyl-2-[1-(4-methoxy-phenyl)-1H-pyrrol-2-yl]-2-oxo-acetamide [ No CAS ]
  • 32
  • [ 5145-71-1 ]
  • N-(4-Chloro-benzyl)-2-[1-(4-methoxy-phenyl)-1H-pyrrol-2-yl]-2-oxo-acetamide [ No CAS ]
  • 33
  • [ 5145-71-1 ]
  • N-[2-(4-Chloro-phenyl)-ethyl]-2-[1-(4-methoxy-phenyl)-1H-pyrrol-2-yl]-2-oxo-acetamide [ No CAS ]
  • 34
  • [ 5145-71-1 ]
  • N-[2-(4-Methoxy-phenyl)-ethyl]-2-[1-(4-methoxy-phenyl)-1H-pyrrol-2-yl]-2-oxo-acetamide [ No CAS ]
  • 35
  • [ 5145-71-1 ]
  • N-[2-(2-Methoxy-phenyl)-ethyl]-2-[1-(4-methoxy-phenyl)-1H-pyrrol-2-yl]-2-oxo-acetamide [ No CAS ]
  • 36
  • [ 5145-71-1 ]
  • N-[2-(4-Chloro-phenyl)-ethyl]-2-hydroxy-2-[1-(4-methoxy-phenyl)-1H-pyrrol-2-yl]-acetamide [ No CAS ]
  • 37
  • [ 5145-71-1 ]
  • N-[2-(2,4-Dichloro-phenyl)-ethyl]-2-[1-(4-methoxy-phenyl)-1H-pyrrol-2-yl]-2-oxo-acetamide [ No CAS ]
  • 38
  • [ 5145-71-1 ]
  • N-[2-(3,4-Dimethoxy-phenyl)-ethyl]-2-[1-(4-methoxy-phenyl)-1H-pyrrol-2-yl]-2-oxo-acetamide [ No CAS ]
  • 39
  • [ 5145-71-1 ]
  • [ 174415-45-3 ]
  • 40
  • [ 5145-71-1 ]
  • [ 174415-36-2 ]
  • 41
  • [ 5145-71-1 ]
  • methyl 4-methyl-3-(N-(4-methoxyphenyl)pyrrol-2-yl)-1H-pyrrole-2-carboxylate [ No CAS ]
  • 42
  • [ 5145-71-1 ]
  • ethyl 4-methyl-3-(N-(4-methoxyphenyl)pyrrol-2-yl)-1H-pyrrole-2-carboxylate [ No CAS ]
  • 45
  • [ 10039-57-3 ]
  • [ 5145-71-1 ]
  • 46
  • [ 109-97-7 ]
  • [ 623-12-1 ]
  • [ 5145-71-1 ]
YieldReaction ConditionsOperation in experiment
20% With copper(II) ferrite; potassium tert-butylate; In N,N-dimethyl-formamide; at 155℃; for 24h;Inert atmosphere; General procedure: To a solution of N-heterocycle (1 equiv), bromobenzene (1.02 equiv) and tBuOK (2 equiv) in dry DMF, CuFe2O4 (10 mol percent) was added and heated at reflux for 24 h under N2 atmosphere. After cooling to room temperature, the mixture was diluted with ethyl acetate and the catalyst was separated by a magnetic separator. The catalyst was washed with ethyl acetate. The combined ethyl acetate layer was washed with water (twice), dried over anhydrous Na2SO4, and concentrated to yield the crude product, which was further purified by silica gel column chromatography using petroleum ether/ethyl acetate to yield N-arylated product.
  • 47
  • [ 5145-71-1 ]
  • [ 129113-00-4 ]
  • [ 1226779-91-4 ]
  • 48
  • [ 5145-71-1 ]
  • [ 3240-34-4 ]
  • [ 1240390-11-7 ]
  • 49
  • [ 696-59-3 ]
  • [ 104-94-9 ]
  • [ 62-53-3 ]
  • [ 635-90-5 ]
  • [ 5145-71-1 ]
YieldReaction ConditionsOperation in experiment
With magnesium iodide etherate; In acetonitrile; at 80℃; General procedure: A Schlenk reaction tube was charged with each amine (5.0 mmol), 2,5-dimethoxytetrahydrofuran (6.0 mmol), MgI2 etherate (10percent mmol), and acetonitrile (10 mL). The reaction mixture was stirred at 80 °C for several hours and then concentrated in vacuo. Flash column chromatography afforded the desired products. The ratio of each product was determined by column chromatography isolation or GC analysis.
  • 50
  • [ 104-92-7 ]
  • [ 51-35-4 ]
  • [ 5145-71-1 ]
  • 51
  • [ 696-62-8 ]
  • [ 51-35-4 ]
  • [ 5145-71-1 ]
YieldReaction ConditionsOperation in experiment
92% With copper(l) iodide; caesium carbonate; In dimethyl sulfoxide; at 110℃; for 24h; General procedure: to a stirred solution of iodo benzene (1.0 mmol) and trans-4-hydroxy-L-proline (2.0 equiv) in dry DMSO (3.0 mL) at rt was added CuI (20 mol percent) followed by Cs2CO3 (2.5 equiv) and heated at 110 °C for 24 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was allowed to cool, and a 1:1 mixture of ethyl acetate/water (20 mL) was added. The combined organic extracts were dried with anhydrous Na2SO4. The solvent and volatiles were completely removed under vacuum to give the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate, 9:1) to afford the corresponding coupling product.
  • 52
  • [ 5145-71-1 ]
  • [ 1126624-05-2 ]
  • (trans)-5-(1-(4-methoxyphenyl)-1H-pyrrol-2-yl)-2,3-dimethyl-4-phenyl-cyclopent-2-enone [ No CAS ]
  • 54
  • [ 100-17-4 ]
  • [ 5145-71-1 ]
  • 55
  • [ 96-50-4 ]
  • [ 5145-71-1 ]
  • [ 1301718-02-4 ]
  • 56
  • [ 5145-71-1 ]
  • [ 100-01-6 ]
  • [ 1301718-05-7 ]
  • 57
  • [ 5145-71-1 ]
  • [ 62-53-3 ]
  • [ 1301718-03-5 ]
  • 58
  • [ 5145-71-1 ]
  • [ 873-74-5 ]
  • [ 1301718-04-6 ]
  • 59
  • [ 5145-71-1 ]
  • 2,5-dibromo-1-(4-methoxyphenyl)-1H-pyrrole [ No CAS ]
  • 60
  • N-(4-methoxyphenyl)-3-pyrroline [ No CAS ]
  • [ 5145-71-1 ]
  • 61
  • [ 696-59-3 ]
  • [ 5145-71-1 ]
  • [ 19264-74-5 ]
  • 62
  • [ 5145-71-1 ]
  • [ 87413-09-0 ]
  • [ 1428317-11-6 ]
  • 64
  • [ 5145-71-1 ]
  • [ 1147550-11-5 ]
  • [ 1393897-40-9 ]
YieldReaction ConditionsOperation in experiment
92% With Oxone; In methanol; at 20℃; for 0.5h; General procedure: A magnetically stirredmixture of the indole (1.0 mmol) and NH4SCN (114 mg, 1.5 mmol) in MeOH(10 mL), was treated with Oxone (921 mg, 1.5 mmol), and the reaction wasstirred at room temperature until complete consumption of the startingmaterial (TLC). Water (30 mL) was added and the products were extracted withEtOAc (3 10 mL). The organic phase was dried (MgSO4), concentrated underreduced pressure and the residue was purified by chromatography (hexane/EtOAc, 90:10).
  • 65
  • [ 5145-71-1 ]
  • [ 75-52-5 ]
  • [ 1600501-09-4 ]
  • [ 39779-30-1 ]
  • 66
  • [ 5145-71-1 ]
  • [ 4521-61-3 ]
  • (1-(4-methoxyphenyl)-1H-pyrrol-3-yl)(3,4,5-trimethoxyphenyl)methanone [ No CAS ]
  • 67
  • [ 5145-71-1 ]
  • [ 719-98-2 ]
  • 1-(4-methoxyphenyl)-2-((trifluoromethyl)thio)pyrrole [ No CAS ]
  • 68
  • [ 5145-71-1 ]
  • [ 7677-24-9 ]
  • [ 39779-30-1 ]
YieldReaction ConditionsOperation in experiment
38% Trimethylsilyl cyanide (4.50 g, 45 mmol) was added to a stirred solution of phenyliodine bis(trifluoroacetate) (12.9 g, 30 mmol) and BF3·Et2O (8.5 g, 60 mmol) in CH2Cl2 (15 mL) at room temperature. After stirring for 30 min, <strong>[5145-71-1]1-(4-methoxyphenyl)pyrrole</strong> (2.6 g,15 mmol) was added in one portion, and the mixture was stirred for additional 7 h under the same conditions whilst the reaction progress was monitored by TLC. After the reaction was complete, saturated aqueous sodium thiosulfate (80 mL) was added to the mixture. The organic layer was separated, and the aqueous phase was extracted with CH2Cl2. The combined extracts were dried with anhydrous magnesium sulfate and evaporated to dryness. The crude product was purified by column chromatography on silica gel using petroleum ether and ethyl acetate (5:1, v/v) as the eluent to give the pure product<strong>[5145-71-1]1-(4-methoxyphenyl)pyrrole</strong>-2-carbonitrile38 (1.1 g, 38percent yield): m.p.162?164 oC. 1H NMR (CDCl3, 400 MHz) delta 3.79 (s, 3H), 6.34 (t, J =3.0Hz, 1H), 6.91?6.98 (m, 1H), 7.04 (d, J = 4.6 Hz, 1H), 7.18 (t, J = 3.9Hz, 2H), 7.42?7.46 (m, 2H). 13C NMR (CDCl3, 100 MHz) delta 63.5, 104.4,110.7, 113.6, 116.4, 116.8, 122.1, 126.0, 126.1, 127.2, 134.3, 160.4, 163.7.IR (KBr) numax/cm-1 3111, 2920, 2211, 1512.
  • 69
  • [ 5145-71-1 ]
  • [ 33675-45-5 ]
  • 1-(4-methoxyphenyl)-2-((3-methoxyphenyl)ethynyl)-1Hpyrrole [ No CAS ]
  • 70
  • [ 5145-71-1 ]
  • 4-(2,5-diiodo-1H-pyrrol-1-yl)anisole [ No CAS ]
  • 71
  • [ 5145-71-1 ]
  • 2,5-(carbonylchlorobis(triisopropylphosphine)ruthenium(II) vinyl)<SUB>2</SUB>-N-anisolepyrrole [ No CAS ]
  • 72
  • [ 5145-71-1 ]
  • C15H11NO [ No CAS ]
  • 73
  • [ 5145-71-1 ]
  • [ 4899-37-0 ]
  • 1-(4-methoxyphenyl)-2-((trichloromethyl)thio)-1H-pyrrole [ No CAS ]
  • 74
  • [ 5145-71-1 ]
  • N-(3-iodo-4-methoxyphenyl)pyrrole [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% General procedure: To a stirred, cooled (0 °C) solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2-3 mL) were successively added BuLi (about 1.6 M hexanes solution, 1.5 mmol) and, 5 min later, ZnCl2·TMEDA (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0 °C before introduction of the substrate (0.5 mmol) at 0?10 °C. After 2 h at room temperature, a solution of I2 (0.38 g, 1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before addition of an aqueous saturated solution of Na2S2O3 (4 mL) and extraction with AcOEt (3 × 20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. Purification by chromatography on silica gel (the eluent is givenin the product description) led to the compounds 3d and 4d.
  • 75
  • [ 5145-71-1 ]
  • N-(2-methoxy-5-(1-pyrrolyl)phenyl)imidazole [ No CAS ]
  • 76
  • [ 110-65-6 ]
  • [ 104-94-9 ]
  • [ 5145-71-1 ]
  • 77
  • [ 5145-71-1 ]
  • [ 64-17-5 ]
  • [ 909246-38-4 ]
  • C13H15NO3 [ No CAS ]
  • 78
  • [ 5145-71-1 ]
  • C26H35NO2 [ No CAS ]
  • 79
  • [ 5145-71-1 ]
  • [ 23351-09-9 ]
YieldReaction ConditionsOperation in experiment
With boron tribromide; In dichloromethane; at 0 - 20℃; for 4h; General procedure: A flame-dried Schlenk test tube with a magnetic stirring bar was charged with CuI (0.038 mg, 0.0002 mol), Cs2CO3 (0.65 g, 0.002 mol), heterocycle (0.0014mol), 1-bromo-4-methoxybenzene (0.185 g, 0.001 mol) and DMF (10 mL) under N2. A rubber septum was replaced with a glass stopper, and the system was then evacuated twice and back filled with N2. After being stirred at 120 C for 24 h, the reaction mixture was diluted with 2-3 mL of ethyl acetate, filtered through a plug of silica gel, and washed with 30-50 mL of ethyl acetate. The filtrate was concentrated and the resulting residue was purified by column chromatography on silica gel to provide the desired product. A solution of BBr3 (0.23 mL, 0.0025mol) in CH2Cl2 (5 mL) was added dropwise to the solution of 1-(4-methoxyphenyl)-1H-heterocycle (0.001 mol) in CH2Cl2 (10 mL) cooled to 0 C. The resulting solution was stirred for 4 h at room temperature. And the solution was washed by NaHCO3, NH4Cl, NaCl solution in sequence. The CH2Cl2 was dried over anhydrous sodium sulfate, removed under vacuum, and the residue was purified by chromatography on silica gel to yield the 4-(1H-heterocycle -1-yl)phenol.4-(1H-heterocycle -1-yl)phenol (0.001 mol), N,N?-dicyclohexyl carbodiimide (DCC) (0.0012 mol), 4-dimethylaminopyridine (DMAP) (0.0002 mol) in 10 mL chloroform were placed in a Pyrex glass tube, sealed and heated at 80 °C for 12 h. After cooling to room temperature, the white solid was filtrated off, and the solvent was removed under vacuum. The crude product was purified by chromatography on silica gel with to gain the desired products.
  • 80
  • [ 100-66-3 ]
  • [ 5145-71-1 ]
YieldReaction ConditionsOperation in experiment
23%; 56% With benzylidene dichloride; chloro-trimethyl-silane; niobium pentachloride; zinc; In tetrahydrofuran; at 60℃; for 2h;Inert atmosphere; Schlenk technique; General procedure: The same operation as the working example 1 was performed except having used N,N-diallyl- N-(4-methylphenyl) amine (0.203 mL, 1mmol) which is a substrate instead of the N,N-diallyl- p-toluenesulfonamide (0.226 mL, 1mmol) which is a substrate. As a result, N-(4-methylphenyl)-3-pyrroline was obtained with 67percent (N,N-diallyl- N-(4-methylphenyl) amine standard) of yield. N-(4-methylphenyl) pyrrole was obtained as a by-product with 11percent (N,N-diallyl- N-(4-methylphenyl) amine standard) of yield. The inversion rate of N,N-diallyl- N-(4-methylphenyl) amine was 93percent or more. The stilbene [Ph-CH=CH-Ph (Ph: phenyl group)] was generating with 42percent (benzal chloride standard) of yield
  • 82
  • [ 5145-71-1 ]
  • [ 110210-11-2 ]
  • 1-(1-(4-methoxyphenyl)-1H-pyrrol-2-yl)piperidine [ No CAS ]
  • 83
  • (2,4,6-trimethylphenyl)(phenyl)iodonium tosylate [ No CAS ]
  • [ 5145-71-1 ]
  • 9-(4-methoxyphenyl)-1,4-dihydro-1,4-epiminonaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With lithium hexamethyldisilazane; In toluene; at 0 - 20℃; for 9h;Schlenk technique; Inert atmosphere; General procedure: To an oven-dried Schlenk tube was added iodonium salts (0.5 mmol, 1 equiv) and substituted pyrrole (if solid, 2.5 mmol, 5 equiv). The tube was degassed with argon for three times. Then the tube was placed in an ice bath. Toluene (4.25 mL) and substituted pyrrole (if liquid, 2.5 mmol, 5equiv) were added sequentially via syringe. After being stirred for approximately 10 minutes,LiHMDS (0.75 mL (1 M in toluene), 0.75 mmol, 1.5 equiv) was added via syringe and the mixture was allowed to warm up to room temperature gradually. After TLC indicated that the iodonium salts were completely consumed, the reaction mixture was quenched by addition of an aqueous solution of ammonium chloride (5 mL) and extracted with DCM (10 mL) for three times. The combined organic layers were dried with Na2SO4, filtered and concentrated. The crude products were purified using flash column chromatography on silica gel to afford the desired product.
  • 84
  • [ 1632-83-3 ]
  • [ 5145-71-1 ]
  • C18H15N3 [ No CAS ]
  • 85
  • [ 6117-80-2 ]
  • [ 104-94-9 ]
  • [ 5145-71-1 ]
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 5145-71-1 ]

Aryls

Chemical Structure| 20440-94-2

[ 20440-94-2 ]

4-Methoxy-N-(4-methoxyphenyl)-N-phenylaniline

Similarity: 0.95

Chemical Structure| 701-56-4

[ 701-56-4 ]

4-Methoxy-N,N-dimethylaniline

Similarity: 0.95

Chemical Structure| 15799-79-8

[ 15799-79-8 ]

3-Methoxy-N,N-dimethylaniline

Similarity: 0.95

Chemical Structure| 59194-26-2

[ 59194-26-2 ]

5-Methoxy-2-(1H-pyrrol-1-yl)aniline

Similarity: 0.93

Chemical Structure| 91-68-9

[ 91-68-9 ]

3-Diethylaminophenol

Similarity: 0.89

Ethers

Chemical Structure| 20440-94-2

[ 20440-94-2 ]

4-Methoxy-N-(4-methoxyphenyl)-N-phenylaniline

Similarity: 0.95

Chemical Structure| 701-56-4

[ 701-56-4 ]

4-Methoxy-N,N-dimethylaniline

Similarity: 0.95

Chemical Structure| 15799-79-8

[ 15799-79-8 ]

3-Methoxy-N,N-dimethylaniline

Similarity: 0.95

Chemical Structure| 59194-26-2

[ 59194-26-2 ]

5-Methoxy-2-(1H-pyrrol-1-yl)aniline

Similarity: 0.93

Chemical Structure| 5961-59-1

[ 5961-59-1 ]

4-Methoxy-N-methylaniline

Similarity: 0.88

Related Parent Nucleus of
[ 5145-71-1 ]

Pyrroles

Chemical Structure| 59194-26-2

[ 59194-26-2 ]

5-Methoxy-2-(1H-pyrrol-1-yl)aniline

Similarity: 0.93

Chemical Structure| 52768-17-9

[ 52768-17-9 ]

4-(1H-Pyrrol-1-yl)aniline

Similarity: 0.65

Chemical Structure| 1547645-87-3

[ 1547645-87-3 ]

5-(5-Methylfuran-2-yl)-1H-pyrrole-2-carboxylic acid

Similarity: 0.65

Chemical Structure| 61034-86-4

[ 61034-86-4 ]

(2-(1H-Pyrrol-1-yl)phenyl)methanol

Similarity: 0.63

Chemical Structure| 113602-62-3

[ 113602-62-3 ]

Methyl 3-hydroxy-1-methyl-1H-pyrrole-2-carboxylate

Similarity: 0.59