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[ CAS No. 5784-95-2 ]

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Chemical Structure| 5784-95-2
Chemical Structure| 5784-95-2
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Product Details of [ 5784-95-2 ]

CAS No. :5784-95-2 MDL No. :MFCD00443483
Formula : C15H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :223.27 g/mol Pubchem ID :-
Synonyms :

Safety of [ 5784-95-2 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5784-95-2 ]

  • Downstream synthetic route of [ 5784-95-2 ]

[ 5784-95-2 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 157869-15-3 ]
  • [ 5784-95-2 ]
YieldReaction ConditionsOperation in experiment
> 99% With zinc dibromide; In toluene; at 130℃; for 24h; General procedure: To a stirred solution of the corresponding 2-iodoaniline (6, 1 mmol) in toluene (3 mL) under argon atmosphere were added Pd/CuO-Fe3O4 (50 mg), NaOH (400 mg, 10 mmol), and the corresponding alkyne (2, 1.5 mmol). The resulting mixture was stirred at 130 C until the end of reaction (see Table 6). The catalyst was removed by a magnet and the resulting mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to remove the solvent. The product was purified by chromatography on silica gel (hexane/ethyl acetate) to give the corresponding compounds 7. Yields are included in Table 6. Then, to a stirred solution of 7 (1 mmol) in toluene (4 mL) was added ZnBr2 (225 mg, 1 mmol). The resulting mixture was stirred at 130 C during 24 h. The mixture was quenched with water and extracted with EtOAc. The organic phases were dried over MgSO4, followed by evaporation under reduced pressure to give the pure products 8 in quantitative yields. Physical and spectroscopic data for compounds 7 and 8, as well as literature for known compounds, follow.
91% With silver nitrate; In water; at 130℃;Sealed tube; Sonication; Green chemistry; General procedure: To a sealed tube (10 mL) was added 3-(phenylethynyl)pyridin-2-amine (1a; 50 mg, 0.26 mmol), H2O (2 mL), and AgNO3 (8.7 mg, 0.052 mmol). After ultrasonic oscillation for 5 min, the mixture was stirred at 130 C for about 16 h. The reaction product was filtered, washed with H2O, and dried to give a brown solid; yield: 48 mg (96%); mp 209-210 C; HPLC purity 98%.
  • 2
  • [ 5784-95-2 ]
  • [ 33513-42-7 ]
  • [ 76195-80-7 ]
YieldReaction ConditionsOperation in experiment
90% General procedure: Under nitrogen gas, phosphorous oxychloride (10 mmol) was added dropwise to dry dimethylformamide (DMF) (10 mmol) while cooling in an ice bath, and the reaction mixture was stirred for 1 h. A solution of compound 4 (1 mmol) in DMF (50 ml) was added dropwise to the mixture with continuous stirring, which was then heated to 70 C. The mixture was poured onto ice cold water (200 mL), naturalized with 40% NaOH, and extracted with chloroform. The chloroform extract was washed with water and dried over Na2SO4. The solvent was removed under vacuum. The residue was crystalized from an ethanol/water mixed solvent system.
90% With trichlorophosphate; at 70℃;Inert atmosphere; General procedure: Under nitrogen gas, phosphorous oxychloride (10 mmol) was added dropwise to dry dimethylformamide (DMF) (10 mmol) while cooling in an ice bath, and the reaction mixture was stirred for 1 h. A solution of compound 3 (1 mmol) in DMF (50 ml) was added dropwise to the mixture with continuous stirring, which was then heated to 70 C. The mixture was poured onto ice cold water (200 mL), naturalized with 40% NaOH, and extracted with chloroform. The chloroform extract was washed with water and dried over Na2SO4.The solvent was removed under vacuum. The residue was crystalized from an ethanol/water mixed solvent system [27].
88% With trichlorophosphate; at 10 - 45℃; for 0.5h; General procedure: Compounds 10a-f were synthesized by known procedure. A solution of 2-aryl-1H-indole 9a-f (0.01 mol) in a minimum amount of DMF was added to the Vilsmeier-Haack reagent (was prepared from phosphorus oxychloride (1 mL) and DMF(3.15 mL)) maintaining the reaction temperature between 10 and 20 C. The reaction mixture was heated at 45 C for 30 min and poured into a mixture of ice-water (100 mL) and 10% aqueous NaOH (20 mL). The resulting mixture was refl uxed for 1 h and cooled to room temperature. The precipitate was collected by filtration, washed with water, dried, and recrystallized.
General procedure: A round-bottomed flask containing (28mL, 370mmol) freshly distilled dimethylformamide (DMF) was cooled to 0C for about 30min and freshly distilled phosphorus oxychloride (8.41mL, 90mmol) was subsequently added with stirring to the DMF over a period of 30min. A solution of indole 19 (85.47mmol) in DMF (10mL, 130mmol) was added to the yellow solution over a period of 1h. The solution was stirred at room temperature till it become a yellow paste. At the end of the reaction, 30g of crushed ice was added to the paste with stirring to make a clear cherry-red aqueous solution. Sodium hydroxide solution (1N, 100mL) was added dropwise with stirring to this cherry-red solution. The resulting suspension was heated rapidly to 90C and allowed to cool at room temperature, after which it was refrigerated for overnight. The product was filtered, washed with water (2×100mL) and air-dried to afford pure indole-3-carboxaldehydes 20 in 80-90% yields. Indole-3-carboxaldehyde, pale yellow solid; mp 194-196C (Lit. [37]196-197C).
General procedure: P-substituted acetophenone (2mmol) and phenyl-hydrazine (2mmol) were poured into a round bottom flask, then CH3COOH (0.5mL) and CH4O3S (27mmol) were added. After the thin layer chromatography (TLC) monitoring reaction was completed, the intermediate 3 was obtained by pouring the mixture into ice water. At -30C, POCl3 (10mmol) was slowly added dropwise to a round bottom flask containing DMF (10mmol), and the reaction was stirred for 1h. After that, intermediate 3 (1mmol) was dissolved in DMF, slowly added dropwise to the flask, and the reaction was heated to 70C with stirring. Monitor the reaction through the TLC. Finally, the mixture was poured into ice water, washed with 40% NaOH solution, and then extracted with DCM to obtain intermediate 4.

  • 3
  • [ 100-63-0 ]
  • [ 100-06-1 ]
  • [ 5784-95-2 ]
YieldReaction ConditionsOperation in experiment
72% General procedure: The appropriate substituted phenylhydrazine (1a-g, 1.0 mmol) and substituted acetophenone (2a-f, 1.0 mmol) were mixed in ethanol (20 mL) and a few drops of glacial AcOH were added. The solution was heated under reflux at 80 C for 1-2 h. The solvents were evaporated in vacuo to give a solid that was added to polyphosphoric acid (PPA) (30 mL), and the mixture slowly heated to 120 C and kept at this temperature for a few hours until the reaction was complete (TLC monitoring). The mixture was allowed to cool and then poured into cold water (50 mL). The acidic solution was neutralised by the slow addition of 1 M NaOH (aq) and the solid precipitate of crude product was collected. Purification by column chromatography (hexane/ethyl acetate) gave the required product(s) (3a-q).
47% With acetic acid; zinc(II) chloride; In neat (no solvent); at 25 - 180℃; for 0.416667h; General procedure: Phenylhydrazine 1a (5.1 mmol) and acetophenone 2a (5 mmol) and anhydrous zinc chloride (200 mol %) were mixed together using pestle in mortar and few drops ofacetic acid (0.1 N) was added drop-wise with continuous mixing at room temperature for 10 min. The mixture was transferred into a round-bottomed flask fitted with a reflux condenser attached with CaCl2 guard tube. Then the mixture was heated slowly up to the temperature of 180 C. The reaction was monitored by TLC using 10% ethyl acetatein n-hexane and the reaction was observed to be completed within 15 min. The mixture was cooled to room temperature and diluted with 5mL dichloromethane and 5mL water. The dichloromethane layer was separated and aqueous layer extracted repeatedly with dichloromethane (3 x 5mL). The combined organic layer was dried over anhydrous Na2SO4, filtered, and solvent was evaporated under reduced pressure. The crude product was purified using flash column chromatography over silica gel using 6% ethyl acetate in hexane as eluent to afford the pure product 2-phenylindole 4a in 86% yield as light yellow solid (Table 1, entry 1).
General procedure: Appropriate amounts of substituted acetophenone 3 (1 mmol) and phenyl hydrazine (1 mmol) were mixed in ethanol (20 mL), and a few drops of glacial acetic acid were added. The solution was heated under reflux at 80 C for 1-2 h. The solvent was evaporated in vacuo to give a solid that was added to polyphosphoric acid (PPA) (30 mL), and the mixture was slowly heated to 120 C and kept at this temperature for a few hours until the reaction was complete (TLC monitoring). The mixture was allowed to cool and then poured into cold water (50 mL). The acidic solution was neutralized by the slow addition of NaOH (1 M), and the solid precipitate of the crude product was collected. Purification by column chromatography (hexane/ethyl acetate) gave the substituted 2-aryl indoles 4a-g.
General procedure: Appropriate amounts of substituted acetophenone 1 (1 mmol) and phenyl hydrazine2 (1 mmol) were mixed in ethanol (20 mL), and a few drops of glacial acetic acid were added. The solution was heated under reflux at 80 C for 1-2 h. The solvent was evaporated in vacuo to give a solid that was added to polyphosphoric acid (30 mL), and the mixture was slowly heated to 120 C and kept at this temperature for a few hours until the reaction was complete (TLC monitoring). The mixture was allowed to cool and then poured into cold water (50 mL). The acidic solution was neutralized by the slow addition of NaOH (1 M), and the solid precipitate of the crude product was collected. Purification by column chromatography (hexane/ethyl acetate) gave the substituted 2-aryl indoles 3a-f.
With methanesulfonic acid; acetic acid; at 80℃; General procedure: P-substituted acetophenone (2mmol) and phenyl-hydrazine (2mmol) were poured into a round bottom flask, then CH3COOH (0.5mL) and CH4O3S (27mmol) were added. After the thin layer chromatography (TLC) monitoring reaction was completed, the intermediate 3 was obtained by pouring the mixture into ice water. At -30C, POCl3 (10mmol) was slowly added dropwise to a round bottom flask containing DMF (10mmol), and the reaction was stirred for 1h. After that, intermediate 3 (1mmol) was dissolved in DMF, slowly added dropwise to the flask, and the reaction was heated to 70C with stirring. Monitor the reaction through the TLC. Finally, the mixture was poured into ice water, washed with 40% NaOH solution, and then extracted with DCM to obtain intermediate 4.

  • 5
  • [ 5784-95-2 ]
  • [ 54888-60-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; tin; In ethanol; water; at 90℃; for 4h;Inert atmosphere; General procedure: A magnetic stirrer bar, lindole 7 (5 mmol), and tin powder (2.97 g, 25 mmol) were placed in a roundbottom flask under nitrogen atmosphere. EtOH (15 mL) and conc. HCl (5 mL) was added at room temperature. The mixture was stirred for 4 h at 90 . After being cooled to room temperature,the mixture was poured into 20 wt% KOHaq (20 mL). The resulting suspension was extracted with Et2O (25 mL X 3), and the organic layer was filtered through Celite. The clear filtrate was concentrated under reduced pressure, and the residue was purified by flash silica gel column chromatography (AcOEt / Petroleum ether = 1 / 30) to give rac-1.
  • 6
  • [ 120-72-9 ]
  • [ 696-62-8 ]
  • [ 5784-95-2 ]
YieldReaction ConditionsOperation in experiment
91% With copper(II) bis(2,4-pentanedionate); triphenylphosphine; In toluene; at 80℃; for 10h; Add indole (1.0mmol), p-methoxy iodobenzene (1.2mmol), catalyst Cu(acac)2 to the reaction tube in sequence(0.05mmol), PPh3(0.10 mmol), add 2 mL of solvent toluene, and react at 80 C. for 10 hours. After the reaction is completed, the reaction solution is concentrated, and the corresponding product is obtained by column chromatography. The isolated yield is 91%.
85% With palladium; anhydrous Sodium acetate; In dimethyl sulfoxide; at 120℃; for 24h;Catalytic behavior; General procedure: The DMSO (3 mL) were added in to the ovendried 25 mL R.B.F containing compound 1a (58.57 mg,0.5 mmol, 1 equiv), followed by addition of NaOAc(45.11 mg, 1.1 equiv), Pd NPs (2.39 mg, 2 mol% Pd content:44.48 w/w), iodobenzene 2a (408.02 mg, 2 mmol, 4 equiv).The reaction mixture was stirred at 120 C for 24 h, aftercomplete conversion of starting material (indicated by TLC),the reaction was quenched with water and the organic layerwas extracted with EtOAc (25 × 3) the combined organiclayer was dried over anhydrous Na2SO4the solvent wasevaporated by rotary evaporator and crude compound waspurified by column chromatography (eluent: 2% EA/Hexane)to get the compound 2-phenyl-1H-indole (3a, 88.01 mg,92%).
52% With norborn-2-ene; bis(acetonitrile)palladium(II) chloride; Potassium bicarbonate; In N,N-dimethyl acetamide; water monomer; at 90℃; General procedure: A high pressure tube equipped with a magnetic stirring bar was charged with indole substrate (0.2mmol, 1 equiv.), norbornene (0.4mmol, 2 equiv.), the base (0.4mmol, 2 equiv. K2CO3 or 2 equiv. KHCO3, as indicated),, and PdCl2(MeCN)2 (0.02mmol, 10 mol %). A solution of water (0.5 M) in DMA (1mL) was added via syringe, and then the aryl iodide (0.4mmol, 2 equiv.) was added via syringe. The reaction mixture was then placed in a preheated oil bath at 70 C (or 90 C, as indicated). Vigorous stirring was applied. The reaction was monitored by TLC. Upon completion, the reaction mixture was cooled to room temperature, diluted with EtOAc, and filtered. The filtrate was extracted with H2O (3 times) and brine, the organic phase was concentrated in vacuum to remove the solvent. The residue was directly submitted to flash column chromatography to afford the 2-arylindole product. The spectral data of the products were in accordance with those reported in the literature1.
  • 7
  • [ 143321-89-5 ]
  • [ 768-60-5 ]
  • [ 5784-95-2 ]
  • 8
  • [ 693794-65-9 ]
  • [ 5784-95-2 ]
  • 9
  • [ 62-53-3 ]
  • [ 2632-13-5 ]
  • [ 5784-95-2 ]
YieldReaction ConditionsOperation in experiment
86% With N-methylimidazolium trifluoromethanesulfonate ionic liquid supported on nano-silica; In neat (no solvent); at 110℃; for 0.666667h;Green chemistry; General procedure: To a mixture of aniline, 2-aminopyridine or 1,2-phenylenediamine (1 mmol) and α-bromo ketone (1 mmol), was added [Hmim]OTf(at)nano-SiO2 (0.3 mmol). The reaction mixture was stirred at 110 C (in the case of 1,2-phenylenediamine,the reaction was performed at room temperature) for the appropriate time according to Table 2. The progressof the reaction was monitored by TLC (eluent: ethyl acetate/petroleum ether, 1:20). After completion of the reaction,ethyl acetate (10 mL) was added and the catalyst was separated by simple filtration. Evaporation of the solvent followed by purification of the crude product by column chromatography on silica gel (eluent: ethyl acetate/petroleumether, 1:20) afforded the pure product
  • 10
  • [ 615-43-0 ]
  • [ 100-06-1 ]
  • [ 5784-95-2 ]
YieldReaction ConditionsOperation in experiment
47% General procedure: Potassium tert-butoxide (1.14 g, 10.2 mmol) was added to a stirred solution of the acetophenone (10 mmol) in anhydrous and oxygen-free DMSO. The mixture was stirred for 15 min., when 2-iodoaniline (0.657 g, 3.0 mmol) was added and the reaction was subjected to irradiation with a 400 W mercury lamp. After 3 h, water (50 mL) was added and the reaction products were extracted with CH2Cl2 (2 × 30 mL). The combined organic phases were successively washed with water (20 mL) and brine (20 mL), dried over MgSO4, and the solvent was removed under reduced pressure. The products were obtained in pure form after crystallization from a 20:80 mixture of Et2O and petroleum ether.
  • 13
  • [ 5784-95-2 ]
  • [ 627-41-8 ]
  • 3-methoxy-6-methyl-11H-benzo[a]carbazole [ No CAS ]
  • 14
  • [ 2727-71-1 ]
  • [ 768-60-5 ]
  • [ 5784-95-2 ]
  • 16
  • [ 20939-77-9 ]
  • [ 5784-95-2 ]
  • 17
  • [ 120-72-9 ]
  • [ 104-92-7 ]
  • [ 5784-95-2 ]
  • [ 5782-23-0 ]
  • [ 93597-01-4 ]
  • 18
  • [ 120-72-9 ]
  • [ 5720-07-0 ]
  • [ 5784-95-2 ]
YieldReaction ConditionsOperation in experiment
78% With palladium(II) trifluoroacetate; trifluoroacetic acid; In 1,4-dioxane; water; at 25℃; for 4h;Catalytic behavior; General procedure: To an oven-dried 25 mL RB containing a magnetic stir bar,heterocycle (0.6 mmol, 1.0 equiv), Pd(TFA)2 (0.06 mmol,5 mol%), arylboronic acid (1.2 mmol, 2.0 equiv), TFA (1.2mmol, 2.0 equiv) and 1,4-Dioxane:H2O(1.0M, 3:1 ratio)wasadded and allowed to stir in the presence of air (open atmosphere)at 25 C for 4-12 h. After completion of the reaction,the mixture was filtered through celite and concentrated. Theresulting mixture was diluted with EtOAc (25 mL), washedwith aqueous NaHCO3(2×15 mL). The organic layers werecombined, dried over anhydrous Na2SO4, and concentratedunder reduced pressure. The crude material was purified bycolumn chromatography (SiO2, n-Hexane/EtOAc) to give thedesired arylated product.
  • 20
  • C20H22ClNO3 [ No CAS ]
  • [ 5784-95-2 ]
  • 2-(4-methoxyphenyl)-1H-indole-1-carboxylic acid 1,1-dimethylethyl ester [ No CAS ]
  • 21
  • [ 4248-19-5 ]
  • [ 149457-45-4 ]
  • [ 5784-95-2 ]
  • 22
  • [ 5784-95-2 ]
  • [ 1109231-82-4 ]
  • [ 1189355-96-1 ]
  • 23
  • [ 5784-95-2 ]
  • [ 1189355-66-5 ]
  • [ 1189355-97-2 ]
  • 24
  • [ 5784-95-2 ]
  • [ 1189355-68-7 ]
  • [ 1189356-02-2 ]
  • 25
  • [ 5784-95-2 ]
  • [ 59738-58-8 ]
  • [ 1189355-78-9 ]
  • 26
  • [ 5784-95-2 ]
  • [ 95969-84-9 ]
  • [ 1189355-92-7 ]
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