Home Cart 0 Sign in  

[ CAS No. 120-72-9 ] {[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 for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 120-72-9
Chemical Structure| 120-72-9
Structure of 120-72-9 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 120-72-9 ]

Related Doc. of [ 120-72-9 ]

Alternatived Products of [ 120-72-9 ]

Product Details of [ 120-72-9 ]

CAS No. :120-72-9 MDL No. :MFCD00005607
Formula : C8H7N Boiling Point : -
Linear Structure Formula :- InChI Key :SIKJAQJRHWYJAI-UHFFFAOYSA-N
M.W :117.15 Pubchem ID :798
Synonyms :
Indole

Calculated chemistry of [ 120-72-9 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.3
TPSA : 15.79 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) : -5.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 2.05
Log Po/w (WLOGP) : 2.17
Log Po/w (MLOGP) : 1.57
Log Po/w (SILICOS-IT) : 2.66
Consensus Log Po/w : 1.98

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.6
Solubility : 0.296 mg/ml ; 0.00252 mol/l
Class : Soluble
Log S (Ali) : -2.01
Solubility : 1.14 mg/ml ; 0.00977 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.23
Solubility : 0.069 mg/ml ; 0.000589 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 120-72-9 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P264-P270-P273-P280-P301+P312+P330-P302+P352+P312-P305+P351+P338-P337+P313-P391-P405-P501 UN#:2811
Hazard Statements:H302-H311-H319-H400 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 120-72-9 ]

* 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 [ 120-72-9 ]

[ 120-72-9 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 120-72-9 ]
  • [ 50-00-0 ]
  • [ 1968-05-4 ]
YieldReaction ConditionsOperation in experiment
94.1% With toluene-4-sulfonic acid; In ethanol; water; at 40 - 50℃; for 3h; Add 280 grams of water to the 1L three-neck bottle. 120 grams of ethanol, 100.0 grams, 15.4 g of paraformaldehyde and 14.7 g of p-toluenesulfonic acid, The reaction was carried out at 40-50 C for 3 hours, and the stirring was stopped after the reaction was almost complete by TLC. Filtration and washing with ethanol to obtain crude 3,3'-dimethane. The crude product was recrystallized by heating with toluene as a solvent. After the precipitate is completely cooled, it is crystallized and filtered. Dry under low temperature vacuum to obtain 99.0 g of a white solid. The yield was 94.1%.
92% With bromine; In acetonitrile; at 50℃; for 16h; General procedure: A 25-mL flask, equipped with a magnetic stirring bar, was charged with 1H-indole 1a (117mg, 1.0mmol), CH3CN (4.0mL), and benzaldehyde 2a (0.056mL, 0.55mmol), followed by addition of a solution of Br2 (0.0010mL) in CH3CN (1.0mL). The reaction mixture was stirred at 50C for 1min. After 1a was consumed, as indicated by thin-layer chromatography (TLC), the reaction mixture was quenched with aqueous Na2S2O3, cooled to room temperature, poured into 30mL water under stirring, and extracted with CH2Cl2 three times. The extract was dried over anhydrous MgSO4. After removal of solvents, the residue was purified by column chromatography on silica gel (petroleum ether-ethyl acetate=9/1, V/V) to afford the product 3a as a pink solid (158mg, 98% yield).
90% With immobilized hexamine on Fe3O4/SiO2 core/shell nanoparticles tribromide; In neat (no solvent); at 80℃; for 0.166667h; General procedure: A mixture of aldehyde or ketone (1 mmol), indole (2 mmol), and catalyst (0.01 g) was stirred at 80 C for 10 min. The reaction was monitored by TLC. After completion of the reaction, EtOH (3 mL) was added and the catalyst was separated by an external magnet. In the recycling experiment, the separated catalyst was then washed with ethanol and dried in oven to remove residual solvent. The results of synthesis of BIMs under solvent-free conditions at 80 C, are presented in Table 1.
56% With tungsto-vanadophosphoric acid on the surface of pyridine modified Fe3O4 nanoparticle; In neat (no solvent, solid phase); at 100℃; for 0.25h; General procedure: A mixture of carbonyl compound (1 mmol), indole (0.234 g,2 mmol) and the desired amount of the inorganic-organic hybridmaterial HPA/TPI-Fe3O4nanoparticles was stirred at elevated tem-perature (100C) for an appropriate reaction time. After completionof the reaction, as indicated by TLC, acetonitrile (3 ml) was added tothe reaction mixture and the catalyst was removed using an exter-nal magnetic bar. Then, silica gel (?1 g) was added to the filtrate,and after evaporation of the solvent, a dark pinkish solid mixturewas obtained. Purification of the product was performed by shortcolumn chromatography eluted with ethylacetate/petroleum ether(1/9) to give a pinkish solid product in high yield. Products wereknown compounds and were identified by means of IR and1H NMRspectroscopy and/or comparison of their melting points with thosereported in the literature.
42% With Fe3O4(at)C-PW (12-Tungstophosphoric acid immobilized on carbon-coated Fe3O4 nanoparticles); In water; at 20℃; for 0.5h; General procedure: A mixture of aldehyde (1 mmol), indole (2 mmol), catalyst (0.15 g), and H2O (5 mL) was stirred at room temperature. At the end of the reaction, water was removed from the mixture by centrifugation followed by decantation. The product was dissolved in acetonitrile, and the catalyst was separated from the product by an external magnet. The solvent was evaporated in vacuum to give the product, which was purified by column chromatography on silica gel using EtOAc/petroleum ether as eluent.
40% With boron trifluoride diethyl etherate; In diethyl ether; at 20℃; for 2h; General procedure: BF3·Et2O (21.3 mg, 0.15 mmol) was added to a mixture of indole 1 (234.4 mg, 2 mmol) and benzaldehyde 2a (106.1 mg, 1 mmol) in diethyl ether (2 mL). The reaction mixture was stirred at room temperature for 2 h in the atmosphere and monitored by TLC. After completion of the reaction, the volatile components were removed using a vacuum rotary evaporator. The resulting residue was purified by column chromatography on silica gel column using EtOAc/petroleum ether solution (1:15-1:8, v/v) as eluent to afford a pink solid bis(indolyl)phenylmethane 3a

Reference: [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 2543 - 2552
[2]RSC Advances,2015,vol. 5,p. 21772 - 21777
[3]Journal of Medicinal Chemistry,2017,vol. 60,p. 3636 - 3655
[4]Journal of the Chinese Chemical Society,2015,vol. 62,p. 321 - 327
[5]Patent: CN110256325,2019,A .Location in patent: Paragraph 0018-0022
[6]Catalysis Communications,2014,vol. 55,p. 11 - 14
[7]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2007,vol. 46,p. 669 - 673
[8]Journal of the Chinese Chemical Society,2014,vol. 61,p. 442 - 446
[9]Research on Chemical Intermediates,2016,vol. 42,p. 8217 - 8226
[10]Synthetic Communications,2011,vol. 41,p. 2446 - 2454
[11]RSC Advances,2016,vol. 6,p. 23008 - 23011
[12]Chemistry Letters,2004,vol. 33,p. 288 - 289
[13]Synthetic Communications,2008,vol. 38,p. 1291 - 1298
[14]Chemistry - A European Journal,2013,vol. 19,p. 14030 - 14033
[15]Australian Journal of Chemistry,2008,vol. 61,p. 359 - 363
[16]Organic Letters,2019,vol. 21,p. 9212 - 9216
[17]Chemical and Pharmaceutical Bulletin,2009,vol. 57,p. 536 - 540
[18]Applied Organometallic Chemistry,2018,vol. 32
[19]Synthesis,2006,p. 3647 - 3653
[20]Applied Catalysis A: General,2013,vol. 468,p. 75 - 87
[21]Heterocycles,2018,vol. 97,p. 163 - 169
[22]Research on Chemical Intermediates,2016,vol. 42,p. 3523 - 3536
[23]Chinese Chemical Letters,2014,vol. 25,p. 406 - 410
[24]Chemistry of Heterocyclic Compounds,1993,vol. 29,p. 553 - 555
    Khimiya Geterotsiklicheskikh Soedinenii,1993,vol. 29,p. 648 - 650
[25]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1956,vol. 304,p. 26,30
[26]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1956,vol. 304,p. 26,30
[27]Canadian Journal of Chemistry,1953,vol. 31,p. 775,777
[28]Chemische Berichte,1954,vol. 87,p. 692,696
[29]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2009,vol. 48,p. 267 - 272
[30]Applied Organometallic Chemistry,2019,vol. 33
[31]Bioorganic Chemistry,2019,vol. 93
  • 2
  • [ 120-72-9 ]
  • [ 87-52-5 ]
  • [ 1968-05-4 ]
  • 3
  • [ 120-72-9 ]
  • [ 72687-70-8 ]
  • [ 1968-05-4 ]
  • 4
  • [ 120-72-9 ]
  • [ 19260-03-8 ]
  • [ 1968-05-4 ]
  • 5
  • [ 120-72-9 ]
  • [ 3010-02-4 ]
  • [ 771-51-7 ]
  • [ 74-90-8 ]
  • [ 1968-05-4 ]
  • [ 109-89-7 ]
  • 6
  • [ 120-72-9 ]
  • [ 3010-02-4 ]
  • [ 1968-05-4 ]
  • 7
  • [ 858232-12-9 ]
  • [ 120-72-9 ]
  • [ 1968-05-4 ]
  • 9
  • [ 120-72-9 ]
  • [ 20503-92-8 ]
  • [ 1968-05-4 ]
  • 10
  • [ 120-72-9 ]
  • [ 71254-91-6 ]
  • [ 1968-05-4 ]
  • 11
  • [ 15121-84-3 ]
  • [ 120-72-9 ]
YieldReaction ConditionsOperation in experiment
100% Pd-C; REFERENTIAL EXAMPLE 2 The procedures of Referential Example 1 were repeated except that the catalyst and the reaction time were changed to 0.59 g of 5% Pd-C of Nippon Engelhard Ltd. and 1.5 hours. The conversion of 2-(o-nitrophenyl)ethanol was 100% and the yield of indole was 39.2%.
92% With C28H28ClNO2Ru; oxygen; potassium carbonate; In isopropyl alcohol; at 130℃; for 6h; Application Example 1 : In an air atmosphere (presence of oxygen), placed in a magnetic Teflon tube in a high pressure reactor, ruthenium added as shown in formula (A2) of the complex structure of 5mg (0.01mmol, 3mol% equivalent of catalyst ), 0.3mmol 2- (2- nitrophenyl) ethanol, 3ml isopropanol and 0.3mmol of potassium carbonate, stirred at 130 6 hours. After completion of the reaction, the solvent was removed using a rotary evaporator, transferred to a separatory funnel and extracted with diethyl ether and water were added, the organic layers were combined, column chromatography to give indole (32 mg of, 92% yield).
  • 12
  • [ 108-94-1 ]
  • [ 100-63-0 ]
  • [ 120-72-9 ]
  • [ 83-34-1 ]
  • [ 3484-18-2 ]
  • 13
  • [ 120-72-9 ]
  • [ 15441-06-2 ]
  • [ 158585-49-0 ]
  • 14
  • [ 120-72-9 ]
  • [ 67-56-1 ]
  • [ 1968-05-4 ]
YieldReaction ConditionsOperation in experiment
70% With sodium triflate; at 80℃; for 24h; In this example, 0.5 mmol of indole was added to 2.5 mL of methanol,Further, 1.0 molpercent of the above catalyst based on the molar amount of indole,One equivalent of base was added to indole to prepare a reaction solution,The reaction solution was kept in the air at 60 ° C. for 20 hours,Synthesis of indole derivatives according to the following formula was carried out.
  • 15
  • [ 120-72-9 ]
  • [ 67442-07-3 ]
  • α-(1-indolyl)-N-methyl-N-methoxyacetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In hexane; water; N,N-dimethyl-formamide; Preparation 1N To a suspension of 8.7 g. (0.22 mole) of a 60percent sodium hydride in hexane dispersion in 100 ml. of DMF was added 21.3 g. (0.18 mole) of indole, and the mixture was stirred for one hour at ambient temperature, cooled to 0° C., diluted with 500 ml. of DMF and then treated with vigorous stirring with 33.1 g. (0.22 mole) of alpha-chloro-N-methyl-N-methoxyacetamide in 75 ml. of DMF. When addition was complete the reaction mixture was quenched with 200 ml. of water and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried and taken to dryness to give 29.4 g. of alpha-(1-indolyl)-N-methyl-N-methoxyacetamide as a slightly purple oil.
  • 16
  • [ 120-72-9 ]
  • [ 75-36-5 ]
  • [ 68-12-2 ]
  • [ 53330-94-2 ]
  • [ 81223-73-6 ]
  • 17
  • [ 120-72-9 ]
  • [ 6624-49-3 ]
  • 1-(1H-Indol-3-yl)-isoquinoline-3-carboxylic acid [ No CAS ]
  • 18
  • [ 120-72-9 ]
  • [ 109-82-0 ]
  • [ 1968-05-4 ]
  • [bis-(1<i>H</i>-indol-3-ylmethyl)-amino]-acetonitrile [ No CAS ]
  • 19
  • [ 120-72-9 ]
  • [ 5457-31-8 ]
  • aqueous NaOH [ No CAS ]
  • [ 1968-05-4 ]
  • 20
  • [ 487-89-8 ]
  • [ 120-72-9 ]
  • [ 1968-05-4 ]
  • [ 258329-25-8 ]
  • C25H18N3(1+)*HO4S(1-) [ No CAS ]
  • 21
  • [ 120-72-9 ]
  • [ 15441-06-2 ]
  • [ 76916-49-9 ]
  • 23
  • [ 120-72-9 ]
  • [ 50-00-0 ]
  • [ 769-42-6 ]
  • [ 1968-05-4 ]
  • [ 33297-14-2 ]
  • 24
  • [ 120-72-9 ]
  • MeX [ No CAS ]
  • [ 6245-89-2 ]
  • 25
  • [ 120-72-9 ]
  • MeX [ No CAS ]
  • [ 75833-63-5 ]
  • 27
  • [ 120-72-9 ]
  • polyindole/s(?) [ No CAS ]
  • [ 75833-63-5 ]
  • 28
  • [ 120-72-9 ]
  • <(η-chlorobenzene)(η-Cp)Fe><PF6> [ No CAS ]
  • [ 22259-53-6 ]
  • 29
  • [ 120-72-9 ]
  • Raney nickel [ No CAS ]
  • [ 75833-63-5 ]
  • 30
  • [ 120-72-9 ]
  • [ 3484-18-2 ]
  • [ 186517-96-4 ]
YieldReaction ConditionsOperation in experiment
Example 5.1.34 Preparation of 3,6-Di-(2-ethylindol-3-yl)-2,5-dihydroxy-1,4-quinone This compound is preferably synthesised by the method of Example 2 using <strong>[3484-18-2]2-ethylindole</strong> as the starting indole. However, this compound may also be prepared by the method of Example 32 using <strong>[3484-18-2]2-ethylindole</strong> as the starting indole. Preparation of <strong>[3484-18-2]2-ethylindole</strong>:
Example 30 Preparation of 3,6-Di-(2-ethylindol-3-yl)-2,5-dihydroxy-1,4-quinone Refer to Example 28 using <strong>[3484-18-2]2-ethylindole</strong> as the starting indole.
  • 31
  • [ 120-72-9 ]
  • [ 50-00-0 ]
  • [ 858232-12-9 ]
  • [ 1968-05-4 ]
YieldReaction ConditionsOperation in experiment
2.1%; 45% With acetic acid; In water; at 50 - 90℃; for 3 - 20h; The one carbon-linked bis-indoles (la-g) were synthesized from indole or 5-substituted indole and formaldehyde, using the method of Jackson et al. (J. Chem. Soc. Perkin Trans. I, 1987, 11: 2543-51 (Scheme 4).R B:HOCH3CO2H HCO2H OHScheme 4 Synthesis of 1C bis-indoles. Ia and Ib produced as a mixture, as were Ic and Id. EPO <DP n="81"/>[00321] Formaldahyde (0.55 eq., 37percent aqueous solution) and acetic acid (0.5 eq.) were added to indole or substituted indole (1.0 - 100 mmol) suspended in H2O and the suspension heated at 9O0C for 8-20 hrs. (Scheme 4). Since 5-hydroxy-indole is sensitive to oxidation, the synthesis of Ig was performed under argon and excluding light, and was heated at only 5O0C for 3 hrs. For the reaction giving la,b, as well as that for lc,d, the beige, gummy mixture was collected by vacuum filtration, washed with water, recrystallized from EtOAc/hexanes and the resulting cream solid purified by flash chromatography using 4: 1 hexanes/EtOAc as eluant. Purification of le-g are given below.Di-(indol-3-yl)methane (Ia):[00322] White crystals (5.55g, 45percent); mp 158-16O0C; 1H NMR: 4.13 (s, 2H),6.91 (t, 2H, J=7.3), 7.03 (t, 2H, J=7.3), 7.13 (s, 2H), 7.31 (d, 2H, J=8.2), 7.51 (d, 2H,J=7.6), 10.72 (s, 2H); 13C NMR: 20.94, 111.32 (2C), 114.21 (2C), 118.04 (2C),118.69 (2C), 120.76 (2C), 122.77 (2C), 127.21 (2C), 136.41 (2C); EI m/z (percent): 246.4(6), 117.8 (100), 89.6 (49); HRMS: CnHi4N2 requires 246.1157, found 246.1147.; 3 -((indol-1-yl) methyl) -indole (\\b):[00323] White crystals (0.262g, 2.1percent); mp 82-840C; 1H NMR: 5.50 (s, 2H),6.38 (d, IH, J=0.6), 7.02 (m, 4H), 7.34 (d, IH, J=8.2), 7.49 (m, 4H), 7.64 (d, IH,J=8.2), 11.03 (s, IH); 13C NMR: 41.29, 100.30, 110.27, 111.02, 111.61, 118.56,118.80 (2C), 120.38, 120.84, 121.29, 124.84, 126.50, 128.30, 128.84, 135.66, 136.36;EI m/z (percent): 246.4 (8), 117.6 (100); HRMS: CnH14N2 requires 246.1157, found246.1168.
25%Chromat.; 65%Chromat. With calcium oxide; In neat (no solvent); at 100℃; for 3h; Indole 1 (8.54 mmol), paraformaldehyde (10.25 mmol) and CaO (145.18 mmol) were blendedwith a magnetic stirrer for the period indicated (TLC) at 100 °C. After reaction, the crude mixture wasextracted with CH2Cl2 and the obtained extract was passed through celite. The concentrated filtratewas ash chromatographed (hexane/ethyl acetate 3/1) on silica gel, obtaining the desired product.
  • 32
  • [ 120-72-9 ]
  • potassium phosphate [ No CAS ]
  • [ 890315-75-0 ]
  • [ 131274-22-1 ]
  • [ 564483-18-7 ]
  • [ 890313-93-6 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; citric acid;tris-(dibenzylideneacetone)dipalladium(0); In ethyl acetate; toluene; Example 407 33 mg of 1H-indole, 0.12 g of cesium carbonate, 5.1 mg of tris(dibenzylideneacetone)dipalladium(0), 1.6 mg of tri-tert-butylphosphine tetrafluoroborate and 4.4 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added to 1.4 mL of toluene solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate at room temperature, and the resulting mixture was heated to reflux under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, 33 mg of 1H-indole, 79 mg of tripotassium phosphate, 5.1 mg of tris (dibenzylideneacetone) dipalladium (0), 1.6 mg of tri-tert-butylphosphine tetrafluoroborate and 4.4 mg of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl were added and the resulting mixture was heated to reflux under nitrogen atmosphere for 4 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10percent citric acid aqueous solution were added and insoluble were removed by filtration. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with a saturated sodium chloride aqueous solution, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia Chemical Ltd., eluent; hexane: ethyl acetate = 20:1] to obtain 45 mg of tert-butyl 2-(benzamido)-4-(1H-indol-1-yl)benzoate as colorless oil. 1H-NMR (CDCl3) delta: 1. 67 (9H, s), 6.73 (1H, d, J = 3.4 Hz), 7.18-7.22 (1H, m), 7.25-7.33 (2H, m), 7.48 (1H, d, J = 3.4 Hz), 7.51-7.62 (3H, m), 7.66-7.70 (1H, m), 7.83 (1H, d, J = 8.3 Hz), 8.06-8.10 (2H, m), 8.17 (1H, d, J = 8.8 Hz), 9.22 (1H, d, J = 2.2 Hz), 12.35 (1H, s).
  • 33
  • [ 120-72-9 ]
  • [ 924-44-7 ]
  • [ 7149-75-9 ]
  • [ 1173165-45-1 ]
  • 34
  • [ 120-72-9 ]
  • [ 50-00-0 ]
  • [ 141-97-9 ]
  • ethyl 2-((1H-indol-3-yl)methyl)-3-oxo-3-phenylpropanoate [ No CAS ]
  • [ 1968-05-4 ]
  • 35
  • [ 120-72-9 ]
  • [ 110-18-9 ]
  • [ 1968-05-4 ]
YieldReaction ConditionsOperation in experiment
62% With copper diacetate; palladium diacetate; at 70℃; for 12h;Neat (no solvent); General procedure: A mixture of substituted indoles (2 mmol), Cu(OAc)2 (1.2 mmol), Pd(OAc)2 (0.1 mmol) and tertiary amines (1.3 mmol) was stirred at 70 °C for 12 h under neat condition. The reaction mixture was dissolved in ethyl acetate and filtered through a plug of Celite. The residue was washed with ethyl acetate (2 .x. 20 mL). The filtrate was washed with 100 mL of water and 10 mL of 0.5 N HCl and the organic layer was collected. The aqueous phase was extracted with ethyl acetate (3 .x. 20 mL). The combined organic phase was washed with saturated sodium chloride solution (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography with ethyl acetate (EA) and petroleum ether (Pet) as eluent to afford the corresponding products and appropriate yield is shown in [Table 2] and [Table 3].
  • 36
  • [ 15121-84-3 ]
  • [ 120-72-9 ]
  • [ 27393-85-7 ]
  • 37
  • [ 120-72-9 ]
  • [ 20232-39-7 ]
  • [ 1450644-41-3 ]
YieldReaction ConditionsOperation in experiment
40% With triethylamine; In neat (no solvent); at 80℃; for 4h; General procedure: In a 10 mL pressurized reaction vial, 0.5 mmolindole (1) or indole-2-carboxylic acid (6), 0.5mmol cyclic imine (2, 4, 9or 12) and Et3N (for theamount used see Table 1) were placed. Thereaction mixture was heated in an oil bath or in a CEM Discover SP MW reactor.The reaction conditions are listed in Tables 1 and 2 and the work-up procedurein the text
  • 38
  • [ 120-72-9 ]
  • [ 230299-21-5 ]
  • [ 1451144-94-7 ]
  • 39
  • [ 120-72-9 ]
  • [ 31899-46-4 ]
  • [ 1968-05-4 ]
  • 41
  • [ 120-72-9 ]
  • [ 391-12-8 ]
  • [ 1616528-74-5 ]
YieldReaction ConditionsOperation in experiment
85% With toluene-4-sulfonic acid; In dichloromethane; at 20℃; for 0.583333h; General procedure: A mixture of the isatin 1 or acenaphthenequinone 4 (1 mmol), indole 2 (2 mmol), p-TSA (10mol percent), CH2Cl2 (10 mL) was added to 50 mL flask and stirred at room temperature until the thecompletion of the reaction (Scheme 1, 2). Then the solid was filtered and washed with CH2Cl2 (5mL) and ethanol (5 mL) in turns, affording the product in excellent yields, which wasrecrystallized from ethanol to produce pure crystalline products. The products were identified byelemental analysis, MS, 1H NMR, 13C NMR, and IR spectra.
  • 42
  • [ 120-72-9 ]
  • [ 118289-17-1 ]
  • C22H16BrN3 [ No CAS ]
  • 43
  • [ 120-72-9 ]
  • [ 109-87-5 ]
  • [ 1968-05-4 ]
  • 44
  • [ 120-72-9 ]
  • [ 74-96-4 ]
  • [ 3484-18-2 ]
  • 45
  • [ 120-72-9 ]
  • [ 6000-43-7 ]
  • [ 1968-05-4 ]
  • 46
  • [ 120-72-9 ]
  • [ 6245-89-2 ]
  • 47
  • [ 120-72-9 ]
  • [ 67-56-1 ]
  • [ 83-34-1 ]
  • [ 1968-05-4 ]
  • 48
  • [ 120-72-9 ]
  • [ 80-17-1 ]
  • [ 3469-20-3 ]
  • 50
  • [ 120-72-9 ]
  • C19H12F6N2O3 [ No CAS ]
  • [ 1968-05-4 ]
  • 51
  • [ 120-72-9 ]
  • [ 2568-25-4 ]
  • [ 35173-74-1 ]
  • 52
  • [ 120-72-9 ]
  • [ 5235-10-9 ]
YieldReaction ConditionsOperation in experiment
7% With hydrogenchloride; sodium nitrite; In 1,4-dioxane; water; for 2h;pH 2.5;Darkness; General procedure: General Procedure (18): An aqueous solution of 0.25 M NaN02 (1.05 equiv) was acidified with dilute HCI to pH 2.5. To this solution, dioxane (15percent v/v) was added. The flask was protected from light by wrapping with aluminium foil. Indole (1.0 equiv) was added slowly in small portions. The mixture was stirred vigorously for 2 h. The liquid in the reaction flask was decanted out and extracted with ethyl acetate 3 times. The combined organic layer was washed with brine, dried over anhydrous sodium sulphate, concentrated in vacuo and purified by flash silica gel column chromatography to afford the product. Intermediate 29 [b79] 1/-/-indazole-3-car Intermediate 29 [B79] was prepared as a brown solid (514 mg, 3.517 mmol) from indole (5.578g, 47.62 mmol) according to general procedure (18) using 7:3 hexane/ethyl acetate as the eluent for flash silica gel column chromatography. Yield: 7percent. 1H NMR (400 MHz, Acetone) delta: 10.23 (s, 1 H), 8.23 (dt, J = 8.1 , 1.0 Hz, 1 H), 7.74 (dt, J = 8.5, 0.9 Hz, 1 H), 7.55 - 7.48 (m, 1 H), 7.41 - 7.36 (m, 1 H).
7% With hydrogenchloride; water; sodium nitrite; In 1,4-dioxane; at 20℃; for 2h;pH 2.5;Darkness; An aqueous solution of 0.25?M NaNO2 (200?mL, 50?mmol, 1.05 equiv) was acidified with dilute HCl to pH?2.5. To this solution, dioxane (30?mL, 15percent v/v) was added. The flask was protected from light by wrapping with aluminium foil. Indole (5.578?g, 47.62?mmol, 1.0 equiv) was added slowly in small portions. The mixture was stirred vigorously at room temperature for 2?h. The liquid in the reaction flask was decanted out and extracted with ethyl acetate 3 times. The combined organic layer was washed with brine, dried over anhydrous sodium sulphate, concentrated in vacuo and purified by flash silica gel column chromatography (7:3 hexane/ethyl acetate) to afford intermediate 18 as a brown solid (514?mg, 3.517?mmol). Yield: 7percent. 1H NMR (400?MHz, Acetone-d6) delta: 10.23 (s, 1H), 8.23 (dt, J?=?8.1, 1.0?Hz, 1H), 7.74 (dt, J?=?8.5, 0.9?Hz, 1H), 7.55-7.48 (m, 1H), 7.41-7.36 (m, 1H).
  • 53
  • [ 120-72-9 ]
  • C15H21NO6S [ No CAS ]
  • [ 1968-05-4 ]
  • C17H22N2O4 [ No CAS ]
  • 54
  • [ 120-72-9 ]
  • ethanolic ethoxymethanol [ No CAS ]
  • [ 1968-05-4 ]
YieldReaction ConditionsOperation in experiment
96% With iron(III) sulphate monohydrate; In ethanol; at 20℃; for 10h; General procedure: Indole (1.17g, 10mmol), substrate (5 mmol), Fe2(SO4)3·xH2O (300 mg), and EtOH (10 mL) were combined in a round-bottomed flask. The resulting mixture was refluxed for the indicated time. The EtOH was removed at reduced pressure. The resulting residue was extracted into EA, washed with water, dried with MgSO4, and then filtered. The product was then purified by column chromatography.
  • 55
  • [ 120-72-9 ]
  • [ 407-97-6 ]
  • [ 407-25-0 ]
  • C15H15F4NO [ No CAS ]
  • 56
  • [ 120-72-9 ]
  • [ 670-98-4 ]
  • [ 98508-67-9 ]
YieldReaction ConditionsOperation in experiment
40% With 1-butyl-3-methylimidazolium heptachlorodialuminate; at 20℃; for 0.5h;Sealed tube; Sonication; Green chemistry; General procedure: An amount of sulfinic ester (1 mmol), [Bmim][Al2Cl7] (1.2 mmol, 0.530 g) and aromatic compound(1 mmol) were sequentially added into a test-tube (d = 1.5 cm, h = 16 cm) sealed with its cap. Theflask was placed into an ultrasound bath where the mixture of reactants was exposed to ultrasoundirradiation for a specific period of time. Subsequently, the reaction mixture was extracted with ethylacetate (3 15 mL). The combined extracts were dried by anhydrous Na2SO4. After the removal ofthe solvent by rotary evaporation, the residue was purified by column chromatography using eluentas a mixture of n-hexane and ethyl acetate.
  • 57
  • [ 120-72-9 ]
  • [ 50-00-0 ]
  • [ 5031-11-8 ]
  • [ 858232-12-9 ]
  • [ 1968-05-4 ]
  • 58
  • [ 120-72-9 ]
  • [ 711-33-1 ]
  • C18H14F3NO [ No CAS ]
  • 59
  • [ 120-72-9 ]
  • [ 2645-22-9 ]
  • 3-(pyridin-4-ylthio)-1H-indole [ No CAS ]
  • 60
  • [ 120-72-9 ]
  • [ 57103-20-5 ]
  • C34H23N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With palladium diacetate; benzyltri(n-butyl)ammonium chloride; potassium carbonate; In toluene; for 48h;Reflux; 3,6-Dibromo-9-phenyl-9H-carbazole (10.0 g, 24.9 mmol), indole (7.0 g, 59.8 mmol)1.56 g (5.0 mmol) of BnBu3NCl,0.56 g (2.5 mmol) of Pd (OAc) 2,20.7 g (149.6 mmol) of K2CO3 are slowly added to 100 ml of toluene.And the mixture was refluxed for 48 hours.The reaction solvent was removed, extracted with dichloromethane and distilled water, and the organic layer was subjected to silica gel filtration.The organic solution was removed and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 6: 4 (v / v) to obtain 6.0 g (yield: 51percent) of the intermediate product (A).
  • 61
  • [ 120-72-9 ]
  • [ 69189-19-1 ]
  • (±)-5-bromo-1,3-dihydrospiro[indene-2,3'-indoline] [ No CAS ]
  • 62
  • [ 120-72-9 ]
  • [ 69189-19-1 ]
  • C16H12BrN [ No CAS ]
  • 63
  • [ 120-72-9 ]
  • [ 3484-18-2 ]
  • 2-ethyl-2-(1H-indol-3-yl)indolin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With tert.-butylhydroperoxide; In water; at 100℃; for 24h; A microfiltration at room temperature 25 ml reaction tube by adding 0.4 ml TBHP (70percent aq), add 1 ml water, stirring and mixing. The reaction tube is arranged after the 100 °C in oil bath, and then sequentially weighing 2 - ethyl indole (73 mg, 0.5 mmol) and indole (117 mg, 1 mmol) is added to the reaction tube, and coupled with the built-in condensing tube, for 100 °C reaction in oil bath 24 hours. TLC display raw material after the reaction is complete, the reaction is cooled down to the room temperature, add 10 ml saturated aqueous solution of sodium bicarbonate quenching reaction. For 20 ml ethyl acetate extraction, the combined organic layer after and drying with anhydrous sodium sulfate. The organic layer after concentrating column separation (hexane: ethyl acetate=6:1) to obtain yellow powdery solid 2 - (1H- Indole -3 - yl) -2 - ethyl indole -3 - one 124 mg, yield is 90percent.
  • 64
  • [ 120-72-9 ]
  • [ 5457-31-8 ]
  • [ 1968-05-4 ]
  • 65
  • [ 120-72-9 ]
  • [ 64-18-6 ]
  • [ 1968-05-4 ]
  • 66
  • [ 120-72-9 ]
  • [ 127-19-5 ]
  • [ 1968-05-4 ]
YieldReaction ConditionsOperation in experiment
80% With tert.-butylhydroperoxide; copper(II) ferrite; at 140℃; for 4h; General procedure: In a 2-dram vial equipped with a magnetic stir bar was charged an indole derivative (0.5 ? 0.75mmol), tert-butyl hydroperoxide (TBHP) (0.5 ? 2.25 mmol), CuFe2O4 (0.075 ? 1.125 mmol), andDMA (1.5 ? 2.25 mL). The reaction was heated at 140 °C for 4 to 24 h. The reaction was cooledto room temperature, and the copper ferrite was separated by an external magnet. The motherliquor was diluted with EtOAc (20 mL) and H2O (20 mL). Aqueous layer was further extractedwith EtOAc (2 x 10 mL). Combined organic layers were washed with H2O (20 mL) and brine (2x 20 mL), dried over Na2SO4, filtered, and concentrated. Column chromatography usingappropriate eluent followed by concentrating the fraction of product and drying the residue undervacuum yielded pure product.
  • 67
  • [ 120-72-9 ]
  • [ 59611-52-8 ]
  • 6-fluoro-2-(1H-indol-3-yl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With iron(III) chloride; oxygen; toluene-4-sulfonic acid; In para-xylene; at 150℃; for 10h; 0.5 mmol of 6-fluorotetrahydroquinoline, 0.5 mmol of indole, 6-fluorotetrahydroquinoline, 10percent by weight of ferric chloride,6-fluorotetrahydroquinoline 80percent p-toluenesulfonic acid and 1.2 ml of p-xylene mixed, stirred at 150 °C for 10 hours under oxygen, after cooling, to room temperature, dilute the reaction, filter, take the filtrate The solvent is evaporated under reduced pressure to give a crude product which is purified by column chromatography to afford product 5a.The product was a yellow solid with a yield of 72percent and a purity of 97percent.
  • 68
  • [ 22929-52-8 ]
  • [ 120-72-9 ]
  • 1-(tetrahydrofuran-3-yl)indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With formic acid; 10% palladium hydroxide on charcoal; In water; at 100℃; for 24h;Inert atmosphere; In the reaction tube (20 ml) put in moderate and solder, join the indole (0.2 mmol), palladium hydroxide/carbon (10 muM percent), then the reaction tube vacuum pumping, orifice, repeatedly replacing three times, in the argon atmosphere water (0.5 ml), formic acid (2.0 times equivalent), two hydrogen -3 (2 H) - furanone (3.0 times equivalent) slowly adding the reaction tube injector, the reaction tube is arranged in the 100 degree Celsius in oil bath heating and stirring the reaction. 24 Hours after stopping the reaction, the reaction tube from out in oil bath, natural cooling to room temperature, methylene chloride (15 ml) to extract respectively 3 times, the combined organic phase, saturated salt water for washing, drying with anhydrous sodium sulfate, filtered, after concentrating the filtrate by column chromatography (eluent: petroleum ether/ethyl acetate=40/1) to obtain the final product 3 u, yield 94percent.
  • 69
  • [ 120-72-9 ]
  • [ 141-97-9 ]
  • [ 621-63-6 ]
  • ethyl 4-(1H-indol-3-yl)-2-methyl-4,5-dihydrofuran-3-carboxylate [ No CAS ]
  • 70
  • [ 120-72-9 ]
  • [ 141-97-9 ]
  • [ 621-63-6 ]
  • [ 28921-35-9 ]
  • ethyl 4-(1H-indol-3-yl)-2-methyl-4,5-dihydrofuran-3-carboxylate [ No CAS ]
  • 71
  • [ 120-72-9 ]
  • [ 105-45-3 ]
  • [ 621-63-6 ]
  • methyl 4-(1H-indol-3-yl)-2-methyl-4,5-dihydrofuran-3-carboxylate [ No CAS ]
  • 72
  • [ 120-72-9 ]
  • [ 1694-31-1 ]
  • [ 621-63-6 ]
  • tert-butyl 4-(1H-indol-3-yl)-2-methyl-4,5-dihydrofuran-3-carboxylate [ No CAS ]
  • 73
  • [ 120-72-9 ]
  • [ 542-08-5 ]
  • [ 621-63-6 ]
  • iso-propyl 4-(1H-indol-3-yl)-2-methyl-4,5-dihydrofuran-3-carboxylate [ No CAS ]
  • 74
  • [ 120-72-9 ]
  • [ 123-54-6 ]
  • [ 621-63-6 ]
  • 1-(4-(1H-indol-3-yl)-2-methyl-4,5-dihydrofuran-3-yl)ethan-1-one [ No CAS ]
  • 75
  • [ 120-72-9 ]
  • [ 57279-20-6 ]
  • [ 621-63-6 ]
  • (4-(1H-indol-3-yl)-2-methyl-4,5-dihydrofuran-3-yl)(2-bromophenyl)methanone [ No CAS ]
  • 76
  • [ 120-72-9 ]
  • [ 437-86-5 ]
  • C15H12N2O2 [ No CAS ]
  • 77
  • [ 120-72-9 ]
  • [ 87-51-4 ]
  • [ 1968-05-4 ]
  • 78
  • [ 120-72-9 ]
  • [ 92487-21-3 ]
  • [ 1968-05-4 ]
YieldReaction ConditionsOperation in experiment
61% With copper(l) iodide; caesium carbonate; In 1,4-dioxane; at 110℃;Sealed tube; Inert atmosphere;Catalytic behavior; General procedure: In a 10 mL oven-dried glass sealed tube having a stirring bar, indole-3-tosylhydrazone (1 equiv., 0.64 mmol), indole (1.5 equiv., 0.96 mmol), CuI (10 mol %), Cs2CO3 (2.0 equiv., 1.27 mmol), and 1,4-dioxane (2 mL) as a solvent were added under the nitrogen atmosphere and stirred the reaction mixture at 110oC in an oil bath for overnight. After complete consumption of indole-3-hydrazone on TLC, cooled the reaction mixture to the room temperature and filtered through a pad of celite, and the celite was rinsed with EtOAc. After evaporating the volatiles under the reduced pressure, the residue was purified by column chromatography using a gradient of ethyl acetate and hexanes to afford the corresponding bisindole product in 59% yields. This procedure was used as a general procedure for synthesizing all bisindole derivatives.
  • 79
  • [ 120-72-9 ]
  • [ 487-89-8 ]
  • [ 1968-05-4 ]
  • 80
  • [ 120-72-9 ]
  • [ 670-98-4 ]
  • [ 54491-43-9 ]
YieldReaction ConditionsOperation in experiment
68% With ammonium iodide; 1,10-Phenanthroline; acetic acid; In 1,4-dioxane; at 100℃; for 6h;Sealed tube; General procedure: A Schlenk tube (25 mL) was charged with indole (0.3 mmol), ethyl arylsulfinate (0.4 mmol), NH4I (20 mol%), and 1,10-phenanthroline (10 mol%). 1,4-Dioxane (2 mL) and HOAc (0.5 mL) were added under air atmosphere, the tube was sealed and heated in an oil bath at 100 C for 6 h. The crude mixture was allowed to cool to room temperature. Then, ethyl acetate and saturated aq. solution of NaCl (5 mL) were added and the layers separated. The aqueous phase was washed three times with ethyl acetate (5 mL x 3). The combined organic layers were dried over anhydrous MgSO4 and concentrated in vacuo. The crude was purified by flash column chromatography with Al2O3 (petroleum ether/EtOAc) giving desired products 3a-z and 4a-t.
Same Skeleton Products
Historical Records

Similar Product of
[ 120-72-9 ]

Chemical Structure| 853409-50-4

A1446427[ 853409-50-4 ]

1H-Indole-3a,4,5,6,7,7a-13C6

Reason: Stable Isotope

Related Parent Nucleus of
[ 120-72-9 ]

Indoles

Chemical Structure| 5649-36-5

[ 5649-36-5 ]

2,6-Dimethyl-1H-indole

Similarity: 0.97

Chemical Structure| 5318-27-4

[ 5318-27-4 ]

6-Aminoindole

Similarity: 0.97

Chemical Structure| 30877-30-6

[ 30877-30-6 ]

5,6-Dimethyl-1H-indole

Similarity: 0.97

Chemical Structure| 196205-06-8

[ 196205-06-8 ]

4-Methyl-1H-indol-5-amine

Similarity: 0.94

Chemical Structure| 16096-32-5

[ 16096-32-5 ]

4-Methyl-1H-indole

Similarity: 0.94