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[ CAS No. 16800-68-3 ] {[proInfo.proName]}

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Chemical Structure| 16800-68-3
Chemical Structure| 16800-68-3
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Product Details of [ 16800-68-3 ]

CAS No. :16800-68-3 MDL No. :MFCD00466593
Formula : C10H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :AUMJJQZNOVOCGY-UHFFFAOYSA-N
M.W : 175.18 Pubchem ID :538819
Synonyms :

Calculated chemistry of [ 16800-68-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.86
TPSA : 37.38 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.68
Log Po/w (XLOGP3) : 0.86
Log Po/w (WLOGP) : 0.86
Log Po/w (MLOGP) : 0.79
Log Po/w (SILICOS-IT) : 1.58
Consensus Log Po/w : 1.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.74
Solubility : 3.16 mg/ml ; 0.0181 mol/l
Class : Very soluble
Log S (Ali) : -1.23
Solubility : 10.3 mg/ml ; 0.0591 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.546 mg/ml ; 0.00312 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.55

Safety of [ 16800-68-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16800-68-3 ]

* 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 [ 16800-68-3 ]

[ 16800-68-3 ] Synthesis Path-Downstream   1~47

  • 2
  • [ 16800-68-3 ]
  • [ 2642-37-7 ]
YieldReaction ConditionsOperation in experiment
With pyridine; chlorosulfonic acid Behandeln des Reaktionsprodukts mit konz.Kalilauge;
  • 3
  • [ 4438-85-1 ]
  • [ 16800-68-3 ]
  • [ 63291-66-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In acetic acid
  • 4
  • [ 22948-94-3 ]
  • [ 16800-68-3 ]
YieldReaction ConditionsOperation in experiment
60% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 5℃; for 24h;
  • 5
  • [ 16800-68-3 ]
  • [ 55234-58-7 ]
  • [ 77290-77-8 ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide In methanol for 72h; Ambient temperature;
  • 6
  • [ 16800-68-3 ]
  • [ 55279-29-3 ]
  • [ 77290-78-9 ]
  • 7
  • [ 17537-64-3 ]
  • [ 16800-68-3 ]
  • [ 83813-66-5 ]
  • 8
  • [ 16800-68-3 ]
  • [ 25128-35-2 ]
  • [ 191172-44-8 ]
  • 9
  • [ 16800-68-3 ]
  • [ 42466-67-1 ]
  • [ 139221-42-4 ]
YieldReaction ConditionsOperation in experiment
92% To a cooled (-78C) stirred suspension of sodium hydride (50% in mineral oil, 2.2 equiv. , 44 mmol, 2.11 g) in tetrahydrofuran (30 ml), under a nitrogen atmosphere, was added dropwise, a solution of intermediate u (20 mmol, 3.5 g) in tetrahydrofuran (50 ml) and the reaction was kept at -78C for 30 minutes. A solution of ethoxy- methylene ethyl cyanoacetate (1.1 equiv. , 2.2 mmol, 3.72 g) in tetrahydrofuran (30 ml) was added dropwise at -78C over a period of 15 minutes. The reaction was kept at -78C for 1 hour. The cooling was removed and the mixture was allowed to warm to room temperature overnight. The reaction mixture was poured into ice-water (400 ml) and acidified with concentrated hydrochloric acid to pH = 1. A green precipitate was filtered and dried overnight in open air to afford intermediate v [J. Y. Merour, S. Piroeelle J. Heterocyclic Chem. 1991, 28, 1869-1873] (4.7 g, yield = 92%, purity (LC) > 95%).
  • 10
  • [ 3859-41-4 ]
  • [ 16800-68-3 ]
  • [ 1207516-06-0 ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: 1,3-cyclopentadione; 1-acetyl-2,3-dihydro-1H-indol-3-one With acetic acid for 0.333333h; Stage #2: With triethylamine at 185℃; for 2h; Microwave irradiation; Stage #3: With hydrogenchloride In methanol A1.1 Step 1 : 2-(1-Acetyl-1 H-indol-S-yO-S-hydroxycyclopent^-enone. 1-Acetyl-1 ,2-dihydro-indol-3-one (7.0 g) is suspended in acetic acid (80 ml) and 1 ,3-cyclopentane-dione (3.92 g) is added. The reaction mixture is stirred for 20 min and triethylamine (5.56 ml) is added. The mixture is partitioned into 4 microwave vials and each portion is heated for 2 h at 1850C in the microwave. The reaction mixtures are recombined and concentrated in vacuo. The residue is treated with 2M methanolic hydrochloride solution (20 ml) and further methanol (5 ml) is added, until complete dissolution occurred. The solution is again concentrated in vacuo and the crude product is purified by flash chromatography (silica gel, eluting with ethyl acetate). The product is crystallized from ether / ethyl acetate 9:1 (v/v) to give 6.8 g (66%) of 2-(1-acetyl-1/-/-indol-3-yl)-3-hydroxycyclopent-2-enone.1H-NMR (200 MHz, CDCI3); δ = 2.31 (s, 3H), 2.55-2.82 (m, 5H), 7.19-7.59 (m, 4H), 8.43 (d, J = 7.5 Hz, 1 H).
  • 11
  • [ 16800-68-3 ]
  • [ 93614-80-3 ]
  • C20H17NO3 [ No CAS ]
  • 12
  • [ 16800-68-3 ]
  • [ 58109-40-3 ]
  • [ 99893-13-7 ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 1-acetyl-2,3-dihydro-1H-indol-3-one With potassium <i>tert</i>-butylate In tetrahydrofuran for 0.25h; Schlenk technique; Stage #2: diphenyliodonium hexafluorophosphate In tetrahydrofuran at 30℃; for 10h; Schlenk technique; general procedure for the synthesis of 3aa-3ao General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30°C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products
  • 13
  • [ 16800-68-3 ]
  • [ 1483-73-4 ]
  • [ 99893-13-7 ]
YieldReaction ConditionsOperation in experiment
57% General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products
  • 14
  • [ 175391-06-7 ]
  • [ 16800-68-3 ]
  • [ 1813538-98-5 ]
YieldReaction ConditionsOperation in experiment
37% Stage #1: 1-acetyl-2,3-dihydro-1H-indol-3-one With potassium <i>tert</i>-butylate In tetrahydrofuran for 0.25h; Schlenk technique; Stage #2: di(4-chlorophenyl)iodonium trifluoromethanesulfonate In tetrahydrofuran at 30℃; for 10h; Schlenk technique; general procedure for the synthesis of 3aa-3ao General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30°C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products
  • 15
  • [ 84563-54-2 ]
  • [ 16800-68-3 ]
  • 1-acetyl-2-(4-(tert-butyl)phenyl)indolin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products
  • 16
  • [ 875-79-6 ]
  • [ 16800-68-3 ]
  • 1-(1',2'-dimethyl-1H,1'H-3,3'-biindol-1-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With copper(l) iodide In ethanol at 60℃; for 12h; 1 Example 1 The N- acetyl-3-indolyl-one 1.75g (10mmol), 1,2- dimethyl-indole 1.35g (10mmol) and cuprous iodide 0.19g (1.0mmol) was dissolved in ethanol, was heated to 60 ° C after 12 hours the reaction, extracted with dichloromethane, the organic layers combined, dried over anhydrous sodium sulfate, dichloromethane / methanol to give a white solid product was recrystallized from N- acetyl -3- (indol-3-methyl-N- ) - indole (2.8g, yield 92%),
86% With iodine In 1,2-dichloro-ethane at 80℃; for 24h; Green chemistry; General procedure for the synthesis of 3,3’-biindoles General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 °C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.
  • 18
  • [ 16800-68-3 ]
  • [ 80565-30-6 ]
  • (Z)-2-((4’-chlorobiphenyl-4-yl)methylene)indolin-3-one [ No CAS ]
  • 19
  • [ 16800-68-3 ]
  • [ 80565-30-6 ]
  • 1-acetyl-2-((4’-chlorobiphenyl-4-yl)methylene)indolin-3-one [ No CAS ]
  • 20
  • [ 16800-68-3 ]
  • [ 90035-34-0 ]
  • (Z)-2-((4’-(trifluoromethyl)biphenyl-4-yl)methylene)indolin-3-one [ No CAS ]
  • 21
  • [ 16800-68-3 ]
  • [ 90035-34-0 ]
  • 1-acetyl-2-((4’-(trifluoromethyl)biphenyl-4-yl)methylene)indolin-3-one [ No CAS ]
  • 22
  • [ 16800-68-3 ]
  • [ 179055-29-9 ]
  • (Z)-2-(4-(1-methyl-1H-pyrazol-4-yl)benzylidene)indolin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: piperidine / toluene / 24 h / Reflux 2: potassium hydroxide / methanol; water / 0.75 h / 20 °C
  • 24
  • [ 16800-68-3 ]
  • [ 164334-74-1 ]
  • (Z)-2-((4’-fluorobiphenyl-3-yl)methylene)indolin-3-one [ No CAS ]
  • 25
  • [ 16800-68-3 ]
  • [ 164334-74-1 ]
  • 1-acetyl-2-((4’-fluorobiphenyl-3-yl)methylene)indolin-3-one [ No CAS ]
  • 26
  • [ 16800-68-3 ]
  • [ 116470-54-3 ]
  • (Z)-2-((4’-methylbiphenyl-3-yl)methylene)indolin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: piperidine / toluene / 24 h / Reflux 2: potassium hydroxide / methanol; water / 0.75 h / 20 °C
  • 27
  • [ 16800-68-3 ]
  • [ 116470-54-3 ]
  • 1-acetyl-2-((4’-methylbiphenyl-3-yl)methylene)indolin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With piperidine In toluene for 24h; Reflux;
  • 28
  • [ 16800-68-3 ]
  • [ 139502-80-0 ]
  • (Z)-2-((4’-chlorobiphenyl-3-yl)methylene)indolin-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: piperidine / toluene / 24 h / Reflux 2: potassium hydroxide / methanol; water / 0.75 h / 20 °C
  • 30
  • [ 16800-68-3 ]
  • [ 343604-24-0 ]
  • (Z)-2-((4’-(trifluoromethyl)biphenyl-3-yl)methylene)indolin-3-one [ No CAS ]
  • 31
  • [ 16800-68-3 ]
  • [ 343604-24-0 ]
  • 1-acetyl-2-((4’-(trifluoromethyl)biphenyl-3-yl)methylene)indolin-3-one [ No CAS ]
  • 32
  • [ 2521-13-3 ]
  • [ 16800-68-3 ]
  • 1-(5'-methoxy-1'-methyl-1H,1'H-3,3'-biindol-1-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With iodine; In 1,2-dichloro-ethane; at 80℃; for 24h;Green chemistry; General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.
  • 33
  • [ 13523-92-7 ]
  • [ 16800-68-3 ]
  • 1-(5'-hydroxy-1'-methyl-1H,1'H-3,3'-biindol-1-yl)ethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With iodine; In 1,2-dichloro-ethane; at 80℃; for 24h;Green chemistry; General procedure: To a solution of 1a (35 mg, 0.2 mmol) and 2a (52.4 mg,0.4 mmol) in DCE (3 mL) was added iodine (10 mg, 0.04 mmol). The reaction mixture was heated at 80 °C for 24 h, then cooled to room temperature and quenched with saturated sodium thiosulfate. The mixture was extracted with CH2Cl2, the combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel to afford title compound.
  • 34
  • [ 16800-68-3 ]
  • [ 60811-18-9 ]
  • C16H11ClFNO2 [ No CAS ]
  • 35
  • [ 16800-68-3 ]
  • [ 14369-81-4 ]
  • C22H25NO6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With triphenylphosphine In 5,5-dimethyl-1,3-cyclohexadiene at 50℃; for 24h; Inert atmosphere; General procedure for the P-catalyzed 3,3-disubstituted oxindoles with allenoates General procedure: A mixture of oxindole 1 (0.30 mmol), allenoate 2 (0.75 mmol), PPh3 (0.045 mmol) in xylene (2.0 mL, dried over 4 Å MS) was stirred at 50 °C under Ar atmosphere for 24 h. After completion of the reaction (indicated by TLC), the mixture was quenched with saturated NaCl solution and diluted with EtOAc, followed by washing with H2O and saturated NaCl solution, and finally dried over Na2SO4. The crude product was purified by flash column chromatography to provide the corresponding product 3.
  • 36
  • [ 16800-68-3 ]
  • [ 579-75-9 ]
  • 1-acetyl-3-oxoindolin-2-yl benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With dihydrogen peroxide; potassium iodide In ethyl acetate at 20℃; for 3h; 5 Example 1The preparation method of the N-acetyl derivative of the compound of formula (3a) includes the following steps: General procedure: Add N-acetyl indole 3-one (0.2mmol, 35mg), benzoic acid (0.6mmol, 73.2mg) to a 10mL single-necked bottle, and then add the oxidant H2O2 (1.5 equivalents, 30ul), KI (5mol%, 1.66 mg), 1 mL of ethyl acetate, reaction at room temperature for 5 h, the reaction is completed, silica gel column chromatography (petroleum ether: ethyl acetate 3: 1), the obtained crude product is added to a saturated sodium carbonate solution, extracted with ethyl acetate, and washed with water The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a white solid. NMR and GC-MS confirmed that it was N-acetyl 3-oxoindole derivative 3a. Yield: 85%;
  • 37
  • [ 16800-68-3 ]
  • [ 634-97-9 ]
  • C15H12N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With dihydrogen peroxide; potassium iodide In ethyl acetate at 20℃; for 4.5h; 8 Example 1The preparation method of the N-acetyl derivative of the compound of formula (3a) includes the following steps: General procedure: Add N-acetyl indole 3-one (0.2mmol, 35mg), benzoic acid (0.6mmol, 73.2mg) to a 10mL single-necked bottle, and then add the oxidant H2O2 (1.5 equivalents, 30ul), KI (5mol%, 1.66 mg), 1 mL of ethyl acetate, reaction at room temperature for 5 h, the reaction is completed, silica gel column chromatography (petroleum ether: ethyl acetate 3: 1), the obtained crude product is added to a saturated sodium carbonate solution, extracted with ethyl acetate, and washed with water The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a white solid. NMR and GC-MS confirmed that it was N-acetyl 3-oxoindole derivative 3a. Yield: 85%;
  • 38
  • [ 16800-68-3 ]
  • [ 86-55-5 ]
  • 1-acetyl-3-oxoindolin-2-yl 1-naphthoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With tetrabutylammomium bromide; toluene-4-sulfonic acid In acetonitrile for 7.5h; Electrolysis; Green chemistry;
70% With dihydrogen peroxide; potassium iodide In ethyl acetate at 20℃; for 3h; 10 Example 1The preparation method of the N-acetyl derivative of the compound of formula (3a) includes the following steps: General procedure: Add N-acetyl indole 3-one (0.2mmol, 35mg), benzoic acid (0.6mmol, 73.2mg) to a 10mL single-necked bottle, and then add the oxidant H2O2 (1.5 equivalents, 30ul), KI (5mol%, 1.66 mg), 1 mL of ethyl acetate, reaction at room temperature for 5 h, the reaction is completed, silica gel column chromatography (petroleum ether: ethyl acetate 3: 1), the obtained crude product is added to a saturated sodium carbonate solution, extracted with ethyl acetate, and washed with water The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a white solid. NMR and GC-MS confirmed that it was N-acetyl 3-oxoindole derivative 3a. Yield: 85%;
65% With dihydrogen peroxide; potassium iodide In water; ethyl acetate at 20℃; for 3h;
  • 39
  • [ 488-93-7 ]
  • [ 16800-68-3 ]
  • 1-acetyl-3-oxoindolin-2-yl furan-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tetrabutylammomium bromide; toluene-4-sulfonic acid In acetonitrile for 7.5h; Electrolysis; Green chemistry;
36% With dihydrogen peroxide; potassium iodide In ethyl acetate at 20℃; for 5.5h; 11 Example 1The preparation method of the N-acetyl derivative of the compound of formula (3a) includes the following steps: General procedure: Add N-acetyl indole 3-one (0.2mmol, 35mg), benzoic acid (0.6mmol, 73.2mg) to a 10mL single-necked bottle, and then add the oxidant H2O2 (1.5 equivalents, 30ul), KI (5mol%, 1.66 mg), 1 mL of ethyl acetate, reaction at room temperature for 5 h, the reaction is completed, silica gel column chromatography (petroleum ether: ethyl acetate 3: 1), the obtained crude product is added to a saturated sodium carbonate solution, extracted with ethyl acetate, and washed with water The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a white solid. NMR and GC-MS confirmed that it was N-acetyl 3-oxoindole derivative 3a. Yield: 85%;
30% With dihydrogen peroxide; potassium iodide In water; ethyl acetate at 20℃; for 6h;
  • 40
  • [ 16800-68-3 ]
  • [ 98-89-5 ]
  • 1-acetyl-3-oxoindolin-2-yl cyclohexanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With dihydrogen peroxide; potassium iodide In water; ethyl acetate at 20℃; for 3h;
90% With dihydrogen peroxide; potassium iodide In ethyl acetate at 20℃; for 3h; 15 Example 1The preparation method of the N-acetyl derivative of the compound of formula (3a) includes the following steps: General procedure: Add N-acetyl indole 3-one (0.2mmol, 35mg), benzoic acid (0.6mmol, 73.2mg) to a 10mL single-necked bottle, and then add the oxidant H2O2 (1.5 equivalents, 30ul), KI (5mol%, 1.66 mg), 1 mL of ethyl acetate, reaction at room temperature for 5 h, the reaction is completed, silica gel column chromatography (petroleum ether: ethyl acetate 3: 1), the obtained crude product is added to a saturated sodium carbonate solution, extracted with ethyl acetate, and washed with water The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a white solid. NMR and GC-MS confirmed that it was N-acetyl 3-oxoindole derivative 3a. Yield: 85%;
  • 41
  • [ 16800-68-3 ]
  • [ 480-63-7 ]
  • 1-acetyl-3-oxoindolin-2-yl 2,4,6-trimethylbenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With dihydrogen peroxide; potassium iodide; In ethyl acetate; at 20℃; for 3h; General procedure: Add N-acetyl indole 3-one (0.2mmol, 35mg), benzoic acid (0.6mmol, 73.2mg) to a 10mL single-necked bottle, and then add the oxidant H2O2 (1.5 equivalents, 30ul), KI (5mol%, 1.66 mg), 1 mL of ethyl acetate, reaction at room temperature for 5 h, the reaction is completed, silica gel column chromatography (petroleum ether: ethyl acetate 3: 1), the obtained crude product is added to a saturated sodium carbonate solution, extracted with ethyl acetate, and washed with water The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a white solid. NMR and GC-MS confirmed that it was N-acetyl 3-oxoindole derivative 3a. Yield: 85%;
  • 42
  • [ 16800-68-3 ]
  • [ 621-82-9 ]
  • 1-acetyl-3-oxoindolin-2-yl cinnamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With dihydrogen peroxide; potassium iodide In ethyl acetate at 20℃; for 7h; 19; 20 Example 1The preparation method of the N-acetyl derivative of the compound of formula (3a) includes the following steps: General procedure: Add N-acetyl indole 3-one (0.2mmol, 35mg), benzoic acid (0.6mmol, 73.2mg) to a 10mL single-necked bottle, and then add the oxidant H2O2 (1.5 equivalents, 30ul), KI (5mol%, 1.66 mg), 1 mL of ethyl acetate, reaction at room temperature for 5 h, the reaction is completed, silica gel column chromatography (petroleum ether: ethyl acetate 3: 1), the obtained crude product is added to a saturated sodium carbonate solution, extracted with ethyl acetate, and washed with water The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain a white solid. NMR and GC-MS confirmed that it was N-acetyl 3-oxoindole derivative 3a. Yield: 85%;
79% With dihydrogen peroxide; potassium iodide In water; ethyl acetate at 20℃; for 7h;
  • 43
  • [ 931-03-3 ]
  • [ 16800-68-3 ]
  • 1-acetyl-3-oxoindolin-2-yl 1H-pyrrole-3-carboxylate [ No CAS ]
  • 44
  • [ 16800-68-3 ]
  • [ 3740-52-1 ]
  • 1-acetyl-3-oxoindolin-2-yl 2-(2-nitrophenyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With dihydrogen peroxide; potassium iodide In water; ethyl acetate at 20℃; for 4h;
  • 45
  • [ 16800-68-3 ]
  • [ 936-08-3 ]
  • 1-acetyl-3-oxoindolin-2-yl 2-bromo-4-chlorobenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% With tetrabutylammomium bromide; toluene-4-sulfonic acid In acetonitrile for 8h; Electrolysis; Green chemistry;
  • 46
  • [ 6639-57-2 ]
  • [ 16800-68-3 ]
  • [ 109-63-7 ]
  • C16H9BF2N2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: benzothiazole-2-carboxaldehyde; 1-acetyl-2,3-dihydro-1H-indol-3-one In N,N-dimethyl-formamide at 40℃; for 0.25h; Inert atmosphere; Stage #2: With triethylamine In N,N-dimethyl-formamide for 10h; Inert atmosphere; Stage #3: boron trifluoride diethyl ether complex With triethylamine In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Cooling with ice; 11 Example 11 In a (50 mL) round-bottom flask, 1-acetylindol-3-one (500 mg, 2.8 mmol) and benzothiazole-2-carbaldehyde (457 mg, 2.8 mmol) were added, purged with nitrogen, and N,N- Dimethylformamide (10 mL) was stirred for 15 minutes, placed in a 40°C water bath, followed by addition of triethylamine (0.4 mL) and vigorous stirring for 10 hours, the reaction mixture solution was added to distilled water (500 mL).After standing for some time, the orange intermediate was obtained by filtration and low temperature vacuum drying.The intermediate was added to a 250 mL round-bottom reaction flask, argon was pumped three times, and a dichloromethane solution (50 mL) was added and stirred for 5 minutes, followed by triethylamine (2 mL) at room temperature.After 10 minutes, boron trifluoride ether (2.5 mL) was slowly added dropwise in an ice bath, and the reaction was stopped when the starting material disappeared on TLC.After vacuum concentration, the product was purified by silica gel chromatography (dichloromethane/petroleum ether=1/1) to obtain the pure product (703 mg) as a blue solid, the structural formula is (A11), and the yield was 77%.
  • 47
  • [ 6639-57-2 ]
  • [ 16800-68-3 ]
  • [ 960-71-4 ]
  • C28H19BN2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
85.2% Stage #1: benzothiazole-2-carboxaldehyde; 1-acetyl-2,3-dihydro-1H-indol-3-one In N,N-dimethyl-formamide at 20℃; for 0.25h; Inert atmosphere; Stage #2: With triethylamine In N,N-dimethyl-formamide for 20h; Inert atmosphere; Stage #3: triphenylborane In toluene at 110℃; for 2h; Inert atmosphere; 22 Example 22 In a (50 mL) round-bottom flask, 1-acetylindol-3-one (500 mg, 2.8 mmol) and benzothiazole-2-carbaldehyde (457 mg, 2.8 mmol) were added, purged with nitrogen, and N,N- Dimethylformamide (10 mL) was stirred for 15 minutes, placed in a 20°C water bath, followed by addition of triethylamine (1.1 mL) and vigorous stirring for 20 hours. The reaction mixture solution was added to distilled water (500 mL).After standing for some time, the orange intermediate was obtained by filtration and low temperature vacuum drying.The dry intermediate was added to a 100 mL two-necked round-bottom flask, triphenylboron (2.66 g, 8.4 mmol) was added under nitrogen atmosphere, and redistilled toluene solution (25 mL) was added at the same time, and stirred for 5 minutes.The reaction was then heated to 110°C for 2 hours.It was cooled to room temperature, concentrated in vacuo, and purified by silica gel chromatography (dichloromethane/petroleum ether=7/3) to obtain the target product (1.05 g), the structural formula is (B11), and the yield was 85.2%.
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