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[ CAS No. 75629-57-1 ] {[proInfo.proName]}

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Chemical Structure| 75629-57-1
Chemical Structure| 75629-57-1
Structure of 75629-57-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 75629-57-1 ]

CAS No. :75629-57-1 MDL No. :MFCD01051808
Formula : C16H12ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :ZDRQMXCSSAPUMM-UHFFFAOYSA-N
M.W : 269.73 Pubchem ID :872445
Synonyms :
Chemical Name :1-(4-Chlorobenzyl)-1H-indole-3-carbaldehyde

Calculated chemistry of [ 75629-57-1 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.06
Num. rotatable bonds : 3
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 78.08
TPSA : 22.0 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.61
Log Po/w (XLOGP3) : 3.69
Log Po/w (WLOGP) : 4.16
Log Po/w (MLOGP) : 3.07
Log Po/w (SILICOS-IT) : 4.2
Consensus Log Po/w : 3.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.22
Solubility : 0.0161 mg/ml ; 0.0000598 mol/l
Class : Moderately soluble
Log S (Ali) : -3.84
Solubility : 0.0388 mg/ml ; 0.000144 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.95
Solubility : 0.000306 mg/ml ; 0.00000114 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 75629-57-1 ]

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

Application In Synthesis of [ 75629-57-1 ]

* 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 [ 75629-57-1 ]

[ 75629-57-1 ] Synthesis Path-Downstream   1~93

  • 1
  • [ 487-89-8 ]
  • [ 104-83-6 ]
  • [ 75629-57-1 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydride 1.) DMF, 2.) DMF, room temp., 15 h;
89% With sodium hydride In dimethyl sulfoxide at 20℃; for 2h;
87% With potassium carbonate In acetone for 5h; Heating;
79% Stage #1: Indole-3-carboxaldehyde With caesium carbonate In acetonitrile at 60℃; for 2h; Stage #2: 1-Chloro-4-(chloromethyl)benzene In acetonitrile at 60℃; for 1h; 5.1.3 General procedure A for the synthesis of 7a-42a General procedure: To a solution of indole-aldehyde (435mg 3mmol) in CH3CN (30mL) was added Cs2CO3 (829mg, 6mmol), and the mixture was refluxed for 2h. To this solution, alkyl halide (3.3mmol) was added, and the mixture was heated under reflux for 1h. After the completion of the reaction, the solvent was evaporated under reduced pressure and water was added to the reaction mixture and extracted 3 times for ethyl acetate. The combined organic layers were dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash chromatography.
78% With potassium carbonate In N,N-dimethyl-formamide for 2h; Heating;
77.5% With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide Reflux; General Procedure for the Preparation of 3a-3i. General procedure: Indole-3-carboxaldehyde (1, 5 mmol) was dissolved in appropriate quantity of dimethylformamide (DMF) and 2.4 ml of 1,8-Diazabicycloundec-7-ene was added. Further, 6 mmol appropriate benzyl chloride (2) was added slowly to the mixture and refluxed for >20 hours [21]. The product was extracted by fractionation from ethyl acetate and water. The organic layer was concentrated to give crude product which was then purified using column chromatography (petroleum ether: ethyl acetate).
76% With sodium hydride at 20℃;
With potassium carbonate In N,N-dimethyl-formamide at 80℃;
Stage #1: Indole-3-carboxaldehyde With potassium carbonate In acetone for 0.0833333h; Stage #2: 1-Chloro-4-(chloromethyl)benzene In acetone at 50℃; 4.2.1. Synthesis of variedly substituted benzyl-1H-indole-3-carbaldehyde (3a-i) General procedure: A mixture of indole-3-carbaldehyde (1) (0.35 g, 2.5 mmol) andpotassium carbonate (5 mmol) in acetone (10 ml) was stirred for5 min. Next, variedly substituted benzyl chlorides (2a-i) (2.5mmol) were added into the reaction mixture and stirred at 50 C.Completion of reaction was monitored by TLC. After completionof reaction, the mixture was filtered to remove K2CO3 and concentratedunder vacuum. Obtained crude product was dried andrecrystallized with diethyl ether to afford the pure product (3a-i).
With sodium hydride In acetonitrile at 20℃; for 4h; 4.3. General synthesis procedure for 1-benzyl-1H-indole-3-carbaldehydes (4) General procedure: To the solution of compound 3 (1 equiv) in MeCN was addedNaH (3 equiv) and the Benzyl chloride derivatives (1.5 equiv) atroom temperature. The reaction mixture was stirred at roomtemperature for 4 h. The mixture was extracted with ethyl acetate,washed with brine, dried (Na2SO4), and filtered. The filtrate wasconcentrated in vacuo, and the residue was purified by columnchromatography (silica gel, ethyl acetate/Petroleum ether) to givethe desired product.
Stage #1: Indole-3-carboxaldehyde With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-Chloro-4-(chloromethyl)benzene In dichloromethane for 5h; Inert atmosphere;
With potassium carbonate In N,N-dimethyl-formamide at 80℃;

Reference: [1]Cavrini; Gatti; Roveri; Cesaroni; Mazzoni; Fiorentini [Archiv der Pharmazie, 1984, vol. 317, # 8, p. 662 - 668]
[2]Na, Young-Min; Le Borgne, Marc; Pagniez, Fabrice; Le Baut, Guillaume; Le Pape, Patrice [European Journal of Medicinal Chemistry, 2003, vol. 38, # 1, p. 75 - 87]
[3]Marchand; Le Borgne; Duflos; Robert-Piessard; Le Baut; Ahmadi; Hartmann; Palzer [Pharmacy and Pharmacology Communications, 1998, vol. 4, # 4, p. 211 - 218]
[4]Wang, Guangcheng; Li, Chunyan; He, Lin; Lei, Kai; Wang, Fang; Pu, Yuzi; Yang, Zhuang; Cao, Dong; Ma, Liang; Chen, Jinying; Sang, Yun; Liang, Xiaolin; Xiang, Mingli; Peng, Aihua; Wei, Yuquan; Chen, Lijuan [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 7, p. 2060 - 2079]
[5]Guengoer, Timur; Malabre, Patrice; Teulon, Jean-Marie; Camborde, Francoise; Meignen, Joelle; et al. [Journal of Medicinal Chemistry, 1994, vol. 37, # 25, p. 4307 - 4316]
[6]Chadha, Navriti; Silakari, Om [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 11, p. 2324 - 2330]
[7]James, David A.; Koya, Keizo; Li, Hao; Chen, Shoujun; Xia, Zhiqiang; Ying, Weiwen; Wu, Yaming; Sun, Lijun [Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 19, p. 5164 - 5168]
[8]Zhu, Wufu; Liu, Yajing; Zhai, Xin; Wang, Xiao; Zhu, Yan; Wu, Di; Zhou, Hongyu; Gong, Ping; Zhao, Yanfang [European Journal of Medicinal Chemistry, 2012, vol. 57, p. 162 - 175]
[9]Singh, Pankaj Kumar; Silakari, Om [Bioorganic Chemistry, 2018, vol. 79, p. 163 - 170]
[10]Liu, Hong-Min; Suo, Feng-Zhi; Li, Xiao-Bo; You, Ying-Hua; Lv, Chun-Tao; Zheng, Chen-Xing; Zhang, Guo-Chen; Liu, Yue-Jiao; Kang, Wen-Ting; Zheng, Yi-Chao; Xu, Hai-Wei [European Journal of Medicinal Chemistry, 2019, vol. 175, p. 357 - 372]
[11]Bai, Yujia; Yuan, Jinping; Hu, Xiaoyue; Antilla, Jon C. [Organic Letters, 2019, vol. 21, # 12, p. 4549 - 4553]
[12]Zhu, Wufu; Liu, Yajing; Zhao, Yanfang; Wang, Haiyan; Tan, Li; Fan, Weijie; Gong, Ping [Archiv der Pharmazie, 2012, vol. 345, # 10, p. 812 - 821,10]
  • 2
  • [ 75629-55-9 ]
  • [ 75629-57-1 ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydroxide for 0.5h; Ambient temperature;
  • 3
  • [ 75629-57-1 ]
  • [ 93548-89-1 ]
YieldReaction ConditionsOperation in experiment
With potassium permanganate In water; acetone for 16h; Ambient temperature; Yield given;
With potassium permanganate In water; acetone
  • 5
  • [ 75-52-5 ]
  • [ 75629-57-1 ]
  • 1-(4-chlorobenzyl)-3-(2-nitrovinyl)indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With ammonium acetate for 0.5h; Heating;
  • 6
  • [ 487-89-8 ]
  • [ 75629-57-1 ]
YieldReaction ConditionsOperation in experiment
60% With sodium hydride In N,N-dimethyl-formamide for 20h; Ambient temperature;
  • 7
  • [ 75629-57-1 ]
  • [ 558470-03-4 ]
YieldReaction ConditionsOperation in experiment
96% In tetrahydrofuran at -40℃;
  • 8
  • [ 75629-57-1 ]
  • [ 405275-53-8 ]
YieldReaction ConditionsOperation in experiment
97% In tetrahydrofuran at -40℃;
  • 9
  • [ 101226-33-9 ]
  • [ 75629-57-1 ]
  • [ 926622-89-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5h; Stage #2: oncrasin-1 In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 1h;
  • 10
  • 1-(2-trimethylsilanyl-ethoxymethyl)-1<i>H</i>-imidazo[4,5-<i>b</i>]pyridine [ No CAS ]
  • [ 75629-57-1 ]
  • [1-(4-chloro-benzyl)-1<i>H</i>-indol-3-yl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1<i>H</i>-imidazo[4,5-<i>b</i>]pyridin-2-yl]-methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(2-trimethylsilanyl-ethoxymethyl)-1<i>H</i>-imidazo[4,5-<i>b</i>]pyridine With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5h; Stage #2: oncrasin-1 In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 1h;
  • 11
  • [ 501660-36-2 ]
  • [ 75629-57-1 ]
  • [ 501660-37-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-[1-(2-trimethylsilanylethoxymethyl)-1H-imidazol-4-yl]-pyridine With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5h; Stage #2: oncrasin-1 In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 1h;
  • 12
  • 4,4-dimethyl-2-[1-(2-trimethylsilanyl-ethoxymethyl)-1<i>H</i>-imidazol-4-yl]-4,5-dihydro-oxazole [ No CAS ]
  • [ 75629-57-1 ]
  • [ 926622-97-1 ]
YieldReaction ConditionsOperation in experiment
40% Stage #1: 4,4-dimethyl-2-[1-(2-trimethylsilanyl-ethoxymethyl)-1<i>H</i>-imidazol-4-yl]-4,5-dihydro-oxazole With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5h; Stage #2: oncrasin-1 In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 1h;
  • 13
  • [ 501660-43-1 ]
  • [ 75629-57-1 ]
  • [ 926622-90-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-(((tert-butyldimethylsilyl)oxy)methyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5h; Stage #2: oncrasin-1 In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 1h;
  • 14
  • [ 75629-57-1 ]
  • [ 148720-52-9 ]
  • [1-(4-chloro-benzyl)-1<i>H</i>-indol-3-yl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1<i>H</i>-imidazo[4,5-<i>c</i>]pyridin-2-yl]-methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(2-trimethylsilanylethoxymethyl)-1H-imidazo[4,5-c]pyridine With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 0.5h; Stage #2: oncrasin-1 In tetrahydrofuran; n-heptane; ethylbenzene at -78℃; for 1h;
  • 15
  • [ 75629-57-1 ]
  • [1-(4-chloro-benzyl)-1<i>H</i>-indol-3-yl]-(1<i>H</i>-imidazol-2-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: aq. HCl / ethanol / 2 h / Heating
  • 16
  • [ 75629-57-1 ]
  • [1-(4-chloro-benzyl)-1<i>H</i>-indol-3-yl]-(4-hydroxymethyl-1<i>H</i>-imidazol-2-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: aq. HCl / ethanol / 2 h / Heating
  • 17
  • [ 75629-57-1 ]
  • [1-(4-chloro-benzyl)-1<i>H</i>-indol-3-yl]-(1<i>H</i>-imidazo[4,5-<i>b</i>]pyridin-2-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: aq. HCl / ethanol / 2 h / Heating
  • 18
  • [ 75629-57-1 ]
  • [ 501659-88-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: 40 percent / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: aq. HCl / ethanol / 2 h / Heating
  • 19
  • [ 75629-57-1 ]
  • 2-[1-(4-chloro-benzyl)-1<i>H</i>-indole-3-carbonyl]-1<i>H</i>-imidazole-4-carboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: 40 percent / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: aq. HCl / ethanol / 2 h / Heating 4.1: 89 percent / aq. H2SO4 / Heating
  • 20
  • [ 75629-57-1 ]
  • [1-(4-chloro-benzyl)-1<i>H</i>-indol-3-yl]-(1<i>H</i>-imidazo[4,5-<i>c</i>]pyridin-2-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: 408 mg / MnO2 / CH2Cl2 / 20 °C 3.1: 92 percent / aq. HCl / ethanol / 2 h / Heating
  • 21
  • [ 75629-57-1 ]
  • [ 926622-92-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: 81 percent / TBAF / 20 °C 4.1: MnO2 / CH2Cl2 / 20 °C 5.1: 20 °C 6.1: aq. HCl / ethanol / 2 h / Heating
  • 22
  • [ 75629-57-1 ]
  • 1-{2-[1-(4-chloro-benzyl)-1<i>H</i>-indole-3-carbonyl]-1<i>H</i>-imidazol-4-yl}-propan-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: 81 percent / TBAF / 20 °C 4.1: MnO2 / CH2Cl2 / 20 °C 5.1: 20 °C 6.1: aq. HCl / ethanol / 2 h / Heating 7.1: MnO2 / CH2Cl2 / 20 °C
  • 23
  • [ 75629-57-1 ]
  • 2-[1-(4-chloro-benzyl)-1<i>H</i>-indole-3-carbonyl]-1<i>H</i>-imidazole-4-carboxylic acid dimethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: 40 percent / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: aq. HCl / ethanol / 2 h / Heating 4.1: EDC; DMAP / 20 °C
  • 24
  • [ 75629-57-1 ]
  • [1-(4-Chloro-benzyl)-1H-indol-3-yl]-(4-pyridin-2-yl-1H-imidazol-2-yl)-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: aq. HCl / ethanol / 2 h / Heating
  • 25
  • [ 75629-57-1 ]
  • 2-[1-(4-chloro-benzyl)-1<i>H</i>-indole-3-carbonyl]-1<i>H</i>-imidazole-4-carboxylic acid ethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: 40 percent / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: aq. HCl / ethanol / 2 h / Heating 4.1: EDC; DMAP / 20 °C
  • 26
  • [ 75629-57-1 ]
  • [ 501659-97-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: 81 percent / TBAF / 20 °C 4.1: MnO2 / CH2Cl2 / 20 °C 5.1: 20 °C 6.1: aq. HCl / ethanol / 2 h / Heating
  • 27
  • [ 75629-57-1 ]
  • [1-(4-Chlorobenzyl)-1H-indol-3-yl]-[4-(pyridine-3-carbonyl)-1H-imidazol-2yl]methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: 81 percent / TBAF / 20 °C 4.1: MnO2 / CH2Cl2 / 20 °C 5.1: 20 °C 6.1: aq. HCl / ethanol / 2 h / Heating 7.1: MnO2 / CH2Cl2 / 20 °C
  • 28
  • [ 75629-57-1 ]
  • [ 912962-40-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C
  • 29
  • [ 75629-57-1 ]
  • [ 501660-46-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: 81 percent / TBAF / 20 °C 4.1: MnO2 / CH2Cl2 / 20 °C
  • 30
  • [ 75629-57-1 ]
  • [ 501660-45-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: 81 percent / TBAF / 20 °C
  • 31
  • [ 75629-57-1 ]
  • [ 912962-46-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: 408 mg / MnO2 / CH2Cl2 / 20 °C
  • 32
  • [ 75629-57-1 ]
  • [1-(4-chloro-benzyl)-1<i>H</i>-indol-3-yl]-[1-(2-trimethylsilanyl-ethoxymethyl)-1<i>H</i>-imidazo[4,5-<i>b</i>]pyridin-2-yl]-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C
  • 33
  • [ 75629-57-1 ]
  • [ 912962-41-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: 81 percent / TBAF / 20 °C 4.1: MnO2 / CH2Cl2 / 20 °C 5.1: 20 °C
  • 34
  • [ 75629-57-1 ]
  • [ 501660-38-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C
  • 35
  • [ 75629-57-1 ]
  • [ 912962-42-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C 3.1: 81 percent / TBAF / 20 °C 4.1: MnO2 / CH2Cl2 / 20 °C 5.1: 20 °C
  • 36
  • [ 75629-57-1 ]
  • [ 912962-43-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: 40 percent / tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C
  • 37
  • [ 75629-57-1 ]
  • [ 501660-44-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 0.5 h / -78 °C 1.2: tetrahydrofuran; heptane; ethylbenzene / 1 h / -78 °C 2.1: MnO2 / CH2Cl2 / 20 °C
  • 38
  • [ 75629-57-1 ]
  • 1-(4-chlorobenzyl)-3-(1H-imidazol-1-ylmethyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 20 °C 2: 83 percent / tetrahydrofuran / 5 h / Heating
  • 39
  • [ 75629-57-1 ]
  • 1-(4-chlorobenzyl)-3-(1H-imidazol-1-ylmethyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 85 percent / NaBH4 / methanol / 1 h / 20 °C 2: 46 percent / acetonitrile / 2 h / 20 °C
Multi-step reaction with 2 steps 1: 92 percent / NaBH4 / propan-2-ol / Ambient temperature 2: p-TsOH / 1 h / 100 - 120 °C
  • 40
  • [ 75629-57-1 ]
  • (E)-3-[1-(4-Chloro-benzyl)-1H-indol-3-yl]-acrylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / 9 h / Heating 2: KOH
  • 41
  • [ 75629-57-1 ]
  • (E)-3-[1-(4-Chloro-benzyl)-1H-indol-3-yl]-2-methyl-acrylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetonitrile / 9 h / Heating 2: KOH
  • 42
  • [ 75629-57-1 ]
  • N6-[2-[1-(4-chlorobenzyl)indol-3-yl]ethyl]adenosine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 86 percent / AcONH4 / 0.5 h / Heating 2: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 3: 67 percent / Et3N / ethanol / 6 h / Heating
  • 43
  • [ 75629-57-1 ]
  • (2S,3S,4R,5R)-5-(6-{2-[1-(4-Chloro-benzyl)-1H-indol-3-yl]-ethylamino}-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid cyclopropylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 86 percent / AcONH4 / 0.5 h / Heating 2: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 3: Et3N / ethanol / 6 h / Heating 4: 57 percent / 1N aq. HCl / 3 h / 60 °C
  • 44
  • [ 75629-57-1 ]
  • [ 151410-11-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 86 percent / AcONH4 / 0.5 h / Heating 2: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 3: Et3N / ethanol / 6 h / Heating
  • 45
  • [ 75629-57-1 ]
  • [ 1053748-02-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 86 percent / AcONH4 / 0.5 h / Heating 2: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 3: Et3N / ethanol / 6 h / Heating
  • 46
  • [ 75629-57-1 ]
  • [ 1055039-18-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 86 percent / AcONH4 / 0.5 h / Heating 2: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 3: Et3N / ethanol / 6 h / Heating
  • 47
  • [ 75629-57-1 ]
  • (2S,3S,4R,5R)-5-(6-{2-[1-(4-Chloro-benzyl)-1H-indol-3-yl]-ethylamino}-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid (2-methoxy-ethyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 86 percent / AcONH4 / 0.5 h / Heating 2: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 3: Et3N / ethanol / 6 h / Heating 4: 57 percent / 50percent aq. HCOOH / 1.25 h / 70 °C
  • 48
  • [ 75629-57-1 ]
  • (2S,3S,4R,5R)-5-(6-{2-[1-(4-Chloro-benzyl)-1H-indol-3-yl]-ethylamino}-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-carboxylic acid (2-hydroxy-1,1-dimethyl-ethyl)-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 86 percent / AcONH4 / 0.5 h / Heating 2: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 3: Et3N / ethanol / 6 h / Heating 4: 31 percent / 50percent aq. HCOOH / 1.25 h / 70 °C
  • 49
  • [ 75629-57-1 ]
  • [ 151409-97-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 86 percent / AcONH4 / 0.5 h / Heating 2: 74 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating
  • 50
  • [ 487-89-8 ]
  • [ 75629-57-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 96 percent / benzene / 2 h / Heating; removing the liberated water 2: 84 percent / ethanol / Ambient temperature; overnight; var.: solvent, time 3: 85 percent / 1percent aq. NaOH / 0.5 h / Ambient temperature
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane at 20℃; for 2h; General experimental procedure: General procedure: In a 50ml round bottom flask the appropriate indole carboxaldehyde (1mmol), benzyl halide (1.1mmol), triethylbenzyl ammonium chloride (0.01mmol) and 50% w/v aq NaOH were added to 5 volumes of DCM. The reaction mixture was stirred at room temperature and monitored by TLC. When the reaction was completed, water was added and the mixture extracted into DCM. The organic layer was concentrated under reduced pressure at 40°C and the residue was purified by flash chromatography using methanol/DCM as mobile phase to afford the corresponding N-benzylindole-3-carboxaldehydes in 80-85% yield. The N-benzylindole-3-carboxaldehyde (1mmol) and N,N-dimethylbarbituric acid (1.2mmol) were added to 10 volumes of methanol and the resulting mixture stirred at room temperature. The final product, the appropriate 5-((1-benzyl-1H-indol-3-yl)methylene)-1,3-dimethyl-pyrimidine-2,4,6(1H, 3H,5H)-trione crashed out of the solution once the reaction was complete (1-2h). The final product was filtered and recrystallized from methanol to afford the 5-((1-benzyl-1H-indol-3-yl)methylene)-1,3-dimethyl-pyrimidine-2,4,6-(1H,3H 5H)-trione in 75-90% yield.
Stage #1: Indole-3-carboxaldehyde With sodium hydride Stage #2:
  • 51
  • [ 75629-45-7 ]
  • [ 75629-57-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 84 percent / ethanol / Ambient temperature; overnight; var.: solvent, time 2: 85 percent / 1percent aq. NaOH / 0.5 h / Ambient temperature
  • 52
  • [ 501660-36-2 ]
  • ammonium chloride [ No CAS ]
  • [ 75629-57-1 ]
  • [ 501660-37-3 ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide In tetrahydrofuran; hexane; ethylbenzene; ethyl acetate 2 Synthesis [1-(4-Chloro-benzyl)-1H-indol-3-yl]-(4-pyridin-2-yl-1H-imidazol-2-yl)-methanone Lithium diisopropylamide (2 M solution in petane/ethylbenzene/THF, 57 uL, 0.12 mmol) was added to a stirred solution of 2-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-pyridine (10.5 mg, 0.038 mmol) in dry THF (3 mL) at -78° C. under N2. After 1 hour at this temperature, a solution of N-4-chlorobenzylindole-3-carboxaldehyde (31 mg, 0.12 mmol) in dry THF (1 mL) was then added through a cannula. The resultant clear solution was stirred at -78° C. for 2 hours. The temperature was then allowed to rise to room temperature and the reaction was quenched by the addition of saturated aqueous NH4Cl (5 mL), extracted with dichloromethane (3*10 mL). The organic layer was separated, dried (Na2SO4), and concentrated under reduced pressure. Flash silica gel chromatography (4:1 hexane/ethyl acetate then 2:1 ethyl acetate/hexane then 4:1 ethyl acetate/MeOH) provided the product [1-(4-Chloro-benzyl)-1H -indol-3-yl]-[4-pyridin-2-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanol as a light yellow syrup (18 mg, 87%). 1H NMR δ-0.05 (s, 9H), 0.81 (t, 2H, J=7), 3.38 (t, 2H, J=7), 5.05-5.35 (m, 5H), 6.30 (s, 1H), 6.95-7.30 (m, 9H), 7.45 (d, 1H, J=6), 7.65 (s, 1H), 7.71 (t, 1H, J=6), 8.05 (d, 1H, J=6), 8.60 (d, 1H, J=4)ppm; ESMS calcd for (C30H33ClN4O2Si): 544.2; found: 545.2 (M+H)+.
  • 53
  • [ 501660-40-8 ]
  • [ 75629-57-1 ]
  • [ 501660-41-9 ]
YieldReaction ConditionsOperation in experiment
30% With n-butyllithium In tetrahydrofuran; hexane; dichloromethane; ethyl acetate 3 Synthesis of [1-(4-Chloro-benzyl)-1H-indol-3-yl]-[4-pyridin-2-yl-5-(toluene-4-sulfonyl)-1H-imidazol-2-yl]-meth To a stirred solution of 2-[5-(toluene-4-sulfonyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-pyridine (0.15 g, 0.35 mmol) in dry THF (10 mL) was added 2.5 M n-BuLi solution in hexane (0.21 mL, 0.525 mmol) under N2 at -78° C. After 20 minutes at this temperature, a solution of N-4-chlorobenzylindole-3-carboxaldehyde (0.1 g, 0.37 mmol) in dry THF (3 mL) was then added through a cannula. Stirring was continued at this temperature for 1 hour. The reaction was then quenched with H2O (10 mL) at 0° C. The aqueous solution was extracted with dichloromethane (3*15 mL). Combined dichloromethane solution was washed with brine and dried over Na2SO4. After removal of the solvent under reduced pressure, the crude material was separated by silica gel chromatography (2:1 hexane/ethyl acetate to 2:1 ethyl acetate/hexane) to afford the desired intermediate [1-(4-chloro-benzyl)-1H-indol-3-yl] -[4-pyridin-2-yl-5-(toluene-4-sulfonyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanol as an oil (65 mg, 30%). 1H NMR (CDCl3) δ-0.05 (s, 9H), 0.70 (t, 2h, J=6), 2.55 (s, 3H), 3.2-3.35 (m, 2H), 4.02 (d, 1H, J=7), 5.2-5.4 (m, 2H), 5.41 (s,2H), 6.4 (d, 1H), 7.0-8.0 (m, 16 H), 8.8 (d,1H, J=5). ESMS calcd for (C37H39ClN4O4SSi): 698.6; found: 699.6 (M+H)+.
  • 54
  • [ 487-89-8 ]
  • [ 584-08-7 ]
  • [ 104-83-6 ]
  • [ 75629-57-1 ]
YieldReaction ConditionsOperation in experiment
In water; N,N-dimethyl-formamide 5 1-(4-Chlorobenzyl)-3-formylindole EXAMPLE 5 1-(4-Chlorobenzyl)-3-formylindole Formula (VIII): R1 =H, n=1, R2 =4-chlorophenyl A solution of 58 g of 3-formylindole, 55.9 g of K2 CO3 and 70.9 g of p-chlorobenzyl chloride in 200 ml of DMF is refluxed for 2 h. After cooling, the mixture is poured into 2 l of water and triturated. The precipitate obtained is filtered off, washed with water and then taken up with isopropanol, filtered off, compressed and washed with pentane to give 120 g of a cream-colored solid. Purification by recrystallization from ethanol gives 84.4 g of 1-(4-chlorobenzyl)-3-formylindole melting at 122° C. The following compounds of Examples 6 to 16 were prepared by the method of Example 5:
In N,N-dimethyl-formamide 5 1-(4-Chlorobenzyl)-3-formylindole EXAMPLE 5 1-(4-Chlorobenzyl)-3-formylindole Formula (VIII): R1 =H, n=1, R2 =4-chlorophenyl A solution of 58 g of 3-formylindole, 55.9 g of K2 CO3 and 70.9 g of p-chlorobenzyl chloride in 200 ml of DMF is refluxed for 2 h. After cooling, the mixture is poured into 2 1 of water and triturated. The precipitate obtained is filtered off, washed with water and then taken up with isopropanol, filtered off, compressed and washed with pentane to give 120 g of a cream-colored solid. Purification by recrystallization from ethanol gives 84.4 g of 1-(4-chlorobenzyl)-3-formylindole melting at 122° C. The following compounds of Examples 6 to 16 were prepared by the method of Example 5:
  • 55
  • [ 75629-57-1 ]
  • 1-(4-chlorobenzyl)-3-(2-nitrovinyl)indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonium acetate In nitromethane 17 1-(4-Chlorobenzyl)-3-(2-nitrovinyl)indole EXAMPLE 17 1-(4-Chlorobenzyl)-3-(2-nitrovinyl)indole Formula (IX): R1 =H, n=1, R2 =4-chlorophenyl 80.9 g of 1-(4-chlorobenzyl)-3-formylindole, prepared in Example 5, 18 g of ammonium acetate and 300 ml of nitromethane are refluxed for 30 min. An orange precipitate appears after cooling. It is filtered off and washed with water and then with isopropanol and hexane to give 81.1 g of orange crystals of 1-(4-chlorobenzyl)-3-(2-nitrovinyl)indole. Melting point: 178° C. The nitrovinylindoles of Examples 18 to 28 were prepared by the procedure of Example 17:
With ammonium acetate In nitromethane 17 1-(4-Chlorobenzyl)-3-(2-nitrovinyl)indole EXAMPLE 17 1-(4-Chlorobenzyl)-3-(2-nitrovinyl)indole Formula (IX): R1 =H, n=1, R= 4-chlorophenyl, R3 =R4 =H 80.9 g of 1-(4-chlorobenzyl)-3-formylindole, prepared in Example 5, 18 g of ammonium acetate and 300 ml of nitromethane are refluxed for 30 min. An orange precipitate appears after cooling. It is filtered off and washed with water and then with isopropanol and hexane to give 81.1 g of orange crystals of 1-(4-chlorobenzyl)-3-(2-nitrovinyl)indole. Melting point: 178° C. The nitrovinylindoles of Examples 18 to 28 were prepared by the procedure of Example 17:
  • 56
  • [ 487-89-8 ]
  • [ 622-95-7 ]
  • [ 75629-57-1 ]
YieldReaction ConditionsOperation in experiment
66% With hydrogen; sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h;
251 Synthesis of 1-(4-chlorobenzyl)indole-3-carbaldehyde STR258 EXAMPLE 251 Synthesis of 1-(4-chlorobenzyl)indole-3-carbaldehyde STR258 The same procedures used in Example 1 were repeated except for using 2.98 g of 4-chlorobenzyl bromide and 2.00 g of indole-3-carbaldehyde as a starting material to give 3.42 g of 1-(4-chlorobenzyl)indole-3-carbaldehyde as pale yellow crystals. The yield thereof was found to be 92%. NMR (CDCl3) δ: 5.32 (2H,s), 7.09 (2H,d,J=8.4 Hz), 7.2~7.4 (5H,m), 7.69 (1H,s), 8.3~8.4 (1H,m), 10.05 (1H,s)
With sodium hydride In dimethyl sulfoxide
Stage #1: Indole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 4-chlorobenzyl bromide In N,N-dimethyl-formamide; mineral oil Inert atmosphere; 4.2.3. General procedure for the synthesis of 5a-f General procedure: To a suspension of NaH 60% in oil (2.25 mmol) in dry DMF(0.8 mL/mmol) was added, at 0° C and under nitrogen atmosphere,a solution of indole-3-carboxaldehyde 4 (1 mmol) in dry DMF(2.5 mL/mmol). After stirring for 30 min at room temperature,benzyl bromide 3 (1.2 mmol) was slowly added. On completion, thereaction was quenched by addition of water and the product wasextracted with diethyl ether. The organic layer was dried overNa2SO4, filtered off and concentrated under vacuum. The cruderesiduewas purified by column chromatography (Silica gel, 60-120mesh, 9:1 hexane/ethyl acetate) to obtain the desired aldehyde 5a-f.

  • 57
  • [ 75629-57-1 ]
  • (Z)-5-((1-(4-chlorobenzyl)-1H-indol-3-yl)methylene)thiazolidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
252 Synthesis of 5-[1-(4-chlorobenzyl)indol-3-yl]-methylene-2,4-thiazolidinedione STR259 EXAMPLE 252 Synthesis of 5-[1-(4-chlorobenzyl)indol-3-yl]-methylene-2,4-thiazolidinedione STR259 The same procedures used in Example 2 were repeated except for using 3.40 g of 1-(4-chlorobenzyl)indole-3-carbaldehyde prepared in Example 251 to give 4.57 g of 5-[1-(4-chlorobenzyl)indol-3-yl]methylene-2,4-thiazolidinedione as yellow crystals. The yield thereof was found to be 98%. IR (KBr) cm-1: 1730, 1680, 1590, 1520, 1340, 1320, 1170; NMR (DMSO-d6) δ: 5.59 (2H,s), 7.2~7.4 (6H,m), 7.5~7.6 (1H,m), 7.9~8.0 (1H,m), 8.01 (1H,s), 8.05 (1H,s), 12.33 (1H, bs)
  • 58
  • [ 60-27-5 ]
  • [ 75629-57-1 ]
  • [ 1207733-63-8 ]
  • 59
  • [ 487-89-8 ]
  • [ 75629-57-1 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: Indole-3-carboxaldehyde With sodium hydride In acetonitrile at 5℃; for 0.5h; Stage #2: 4-chlorobenzyl halide In acetonitrile at 20℃; for 12h; Synthesis of N-alkylated indole-3-carbaldehydes General procedure: To a cold solution of indole-3-aldehyde 7 (2.85 mmol) in acetonitrile (7 mL) slowly added sodium hydride (4.20 mmol) at below 5 °C and maintained the resulting mixture for 30 min. Later,respective alkyl halide (4.2 mmol) was added drop wise in a period of 10 min. After completion of addition reaction was allowed to raise to room temperature and maintained for 12h. Upon completion of reaction was indicated by TLC, reaction mixture was poured into ice cold water and extracted with ethylacetate. Organic layer was evaporated under vaccuo and the residue thus obtained was recrystalized with ether to afford pure compounds 8a-d in 90-95% yields.
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane; water at 20℃;
With sodium hydroxide In toluene
Stage #1: Indole-3-carboxaldehyde With potassium carbonate In dimethyl sulfoxide for 0.0833333h; Stage #2: 4-chlorobenzyl halide In dimethyl sulfoxide
Stage #1: Indole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Stage #2: 4-chlorobenzyl halide In N,N-dimethyl-formamide at 0 - 20℃; for 24h; General synthetic procedure for the synthesis of compound F General procedure: In a dried RBF, NaH (1.5 mmol) was added in anhydrous DMF (10 ml), the solution was cooled to 0 oCand indole (1.0 mmol) was added and the reaction was allowed to stir at RT for 30 min. The solutionwas then cooled again to 0 oC and appropriate alkyl/aryl halide (1.1 mmol) was added and the mixturewas allowed to warm to RT and stirred at ambient temperature overnight. The reaction mixture wasquenched with ice water and the aqueous layer was extracted with ethyl acetate. The combined organiclayer was evaporated to leave a residue, which was purified by column chromatography

  • 61
  • [ 487-89-8 ]
  • [ 75629-57-1 ]
YieldReaction ConditionsOperation in experiment
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In dichloromethane; water at 20℃;
  • 62
  • [ 120-72-9 ]
  • [ 75629-57-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: trichlorophosphate 2: sodium hydride / dimethyl sulfoxide
Multi-step reaction with 2 steps 1: trichlorophosphate 2: sodium hydroxide / toluene
Multi-step reaction with 2 steps 1: trichlorophosphate 2: sodium hydride / N,N-dimethyl-formamide
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C 2: trichlorophosphate
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0.5 h / 0 °C 1.2: 3 h / 20 °C 2.1: sodium hydride / acetonitrile / 4 h / 20 °C
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 6.5 h / 0 - 60 °C 2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 2.2: 24 h / 0 - 20 °C

  • 63
  • [ 15317-58-5 ]
  • [ 75629-57-1 ]
  • [ 1354714-41-2 ]
YieldReaction ConditionsOperation in experiment
92% With acetic acid; In ethanol;Reflux; General Procedure: To a mixture of indole-3-carboxaldehyde 2 (1 mmol) and <strong>[15317-58-5]indole-3-carbohydrazide</strong> 4 (1 mmol) in ethanol(10 mL) was added catalytic amount of acetic acid (0.1 mL). The reaction mixture was refluxed for 3-4 h. Progress of the reaction was monitored by thin layer chromatography. Upon completion, the reaction mixture was cooled, and solid mass so obtained was filtered and recrystallized to afford pure bis(indolyl)hydrazide-hydrazones 5a-n in good yields.
  • 64
  • [ 13017-47-5 ]
  • [ 75629-57-1 ]
  • (E)-4,4'-(6-(2-((1-(4-chlorobenzyl)-1H-indol-3-yl)methylene)hydrazinyl)-1,3,5-triazine-2,4-diyl)dimorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With acetic acid In ethanol Reflux;
  • 65
  • [ 299907-60-1 ]
  • [ 75629-57-1 ]
  • (E)-4,4'-(6-(2-((1-(4-chlorobenzyl)-1H-indol-3-yl)methylene)hydrazinyl)pyrimidine-2,4-diyl)dimorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With acetic acid In ethanol Reflux;
  • 66
  • [ 15317-58-5 ]
  • [ 75629-57-1 ]
  • [ 1431138-09-8 ]
  • 67
  • [ 75629-57-1 ]
  • [ 16228-57-2 ]
  • [ 1394046-86-6 ]
YieldReaction ConditionsOperation in experiment
87% With acetic acid In ethanol Reflux;
  • 68
  • [ 1415660-22-8 ]
  • [ 75629-57-1 ]
  • [ 1394047-29-0 ]
YieldReaction ConditionsOperation in experiment
75% With acetic acid In ethanol Reflux;
  • 69
  • [ 1427682-85-6 ]
  • [ 75629-57-1 ]
  • [ 1427683-20-2 ]
YieldReaction ConditionsOperation in experiment
72% With sodium carbonate In methanol for 6h; Reflux;
  • 70
  • [ 607-57-8 ]
  • [ 75629-57-1 ]
  • [ 1425944-32-6 ]
YieldReaction ConditionsOperation in experiment
260mg With KF-Al2O3 In methanol at 85℃; for 18h; l-(4-Chloro-benzyl)-3-(2-nitro-fluoren-9-ylidenemethyl)-lH-indole (CYD-2-21). To a solution of 2-nitrofluorene (250 mg, 1.18 mmol) in 20 mL of methanol was added 1- (4-Chloro-benzyl)-lH-indole-3-carbaldehyde (382 mg, 1.42 mmol) and KF-A1203 (189 mg, 1.18 mmol). The resulting mixture was stirred at 85 °C for 18 hrs. After that, TLC showed that 2- nitrofluorene was gone, and many solids were suspended in MeOH. 260 mg of CYD-2-21 was obtained as a yellow solid after filtration and recrystallization from CH2C12. One isomer: 1H-NMR (600 MHz, d6-DMSO) δ 8.96 (s, 1H), 8.41 (s, 1H), 8.27 (m, 2H), 8.18 (m, 3H), 8.09 (d, 1H, J = 7.2 Hz), 7.78 (d, 1H, J = 7.8 Hz), 7.62 (d, 1H, J = 7.8 Hz), 7.47 (m, 5H), 7.28 (t, 1H, J = 7.2 Hz), 7.20 (t, 1H, J = 7.2 Hz), 5.57 (s, 2H). Another isomer: 1H-NMR (600 MHz, d6- DMSO) δ 9.01 (s, 1H), 8.39 (s, 1H), 8.33 (s, 1H), 8.19 (m, 4H), 7.86 (d, 1H, J = 8.4 Hz), 7.78 (d, 1H, J = 7.8 Hz), 7.62 (d, 1H, J = 7.8 Hz), 7.47 (m, 5H), 7.28 (t, 1H, J = 7.2 Hz), 7.20 (t, 1H, J = 7.2 Hz), 5.59 (s, 2H).13C-NMR (150 MHz, d6-DMSO) δ 147.1, 146.6, 145.6, 142.9, 141.9, 141.0, 138.2, 138.0, 137.0, 136.8, 136.7, 136.4 (2C), 135.6, 132.7, 132.2, 132.1, 130.2, 129.9, 129.8, 129.7, 129.2, 129.1, 129.0 (2C), 128.4, 128.1 (2C), 127.9, 124.5, 124.1, 123.8, 123.2 (2C), 123.1, 122.4, 122.0, 121.7, 121.2, 121.0 (2C), 120.8, 120.6 (2C), 120.2, 118.8, 118.7, 116.2 (2C), 111.5, 111.4, 111.3 (2C), 49.4, 49.2.
  • 72
  • [ 769-42-6 ]
  • [ 75629-57-1 ]
  • [ 328244-22-0 ]
YieldReaction ConditionsOperation in experiment
90% In methanol at 20℃; General experimental procedure: General procedure: In a 50ml round bottom flask the appropriate indole carboxaldehyde (1mmol), benzyl halide (1.1mmol), triethylbenzyl ammonium chloride (0.01mmol) and 50% w/v aq NaOH were added to 5 volumes of DCM. The reaction mixture was stirred at room temperature and monitored by TLC. When the reaction was completed, water was added and the mixture extracted into DCM. The organic layer was concentrated under reduced pressure at 40°C and the residue was purified by flash chromatography using methanol/DCM as mobile phase to afford the corresponding N-benzylindole-3-carboxaldehydes in 80-85% yield. The N-benzylindole-3-carboxaldehyde (1mmol) and N,N-dimethylbarbituric acid (1.2mmol) were added to 10 volumes of methanol and the resulting mixture stirred at room temperature. The final product, the appropriate 5-((1-benzyl-1H-indol-3-yl)methylene)-1,3-dimethyl-pyrimidine-2,4,6(1H, 3H,5H)-trione crashed out of the solution once the reaction was complete (1-2h). The final product was filtered and recrystallized from methanol to afford the 5-((1-benzyl-1H-indol-3-yl)methylene)-1,3-dimethyl-pyrimidine-2,4,6-(1H,3H 5H)-trione in 75-90% yield.
  • 73
  • [ 2231-57-4 ]
  • [ 75629-57-1 ]
  • [ 1598435-79-0 ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: Thiocarbohydrazide With acetic acid In water at 90℃; Stage #2: oncrasin-1 In ethanol; water for 1h; Reflux;
  • 74
  • [ 1393921-62-4 ]
  • [ 75629-57-1 ]
  • [ 1593928-68-7 ]
YieldReaction ConditionsOperation in experiment
203 mg With potassium hydroxide In methanol; water at 0 - 20℃; for 48h; Inert atmosphere; 5.1.4 General procedure B for the synthesis of 3-42 General procedure: A solution of 50% KOH (2mL, aq) was added dropwise to a stirred solution of 2 (1mmol, 1equiv) and indole-aldehyde (1mmol, 1equiv) in methanol (10mL) at 0°C. The resulting mixture was stirred at room temperature for 48h under N2 atmosphere. After the end of reaction, the mixture was poured into ice water and pH was brought back to 7.0 by the careful addition of 1N HCl solution. The aqueous layer was extracted with ethyl acetate, washed with brine, dried (Na2SO4), and then concentrated in vacuo. The residue was purified by silica gel column chromatography to provide 3-42 as a yellow solid.
  • 75
  • [ 33513-42-7 ]
  • [ 85607-00-7 ]
  • [ 75629-57-1 ]
YieldReaction ConditionsOperation in experiment
With trichlorophosphate
Stage #1: N,N-dimethyl-formamide With trichlorophosphate for 0.5h; Stage #2: 1-(4'-chlorobenzyl)-indole at 20℃; for 1h; 4.1.3 General procedure for the synthesis of indole-3-carboxaldehydes (20) General procedure: A round-bottomed flask containing (28mL, 370mmol) freshly distilled dimethylformamide (DMF) was cooled to 0°C 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 90°C 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 194-196°C (Lit. [37]196-197°C).
  • 76
  • [ 1068-57-1 ]
  • [ 75629-57-1 ]
  • N'-((1-(4-chlorobenzyl)-1H-indol-3-yl)methylene)acetohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With acetic acid In ethanol for 4h; Reflux; General procedure for the synthesis of N'-((1-(substituted)-1H-indol-3-yl)methylene)hydrazides (18a-v) General procedure: Indole-3-aldehyde 16 (1 mmol) and the correspondingalkyl/aryl acid hydrazide 17 (1.05 mmol) were refluxed in ethanol (5 mL) in the presence of glacial acetic acid(0.3 mL) for 4 h. On cooling the reaction mixture to roomtemperature, the crude product was precipitated, filteredand dried. Further recrystallization of the crude products inethanol allowed to obtain pure products in 85-95 % yields.
  • 77
  • [ 1538-08-5 ]
  • [ 75629-57-1 ]
  • N'-((1-(4-chlorobenzyl)-1H-indol-3-yl)methylene)-2,2,2-trifluoroacetohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With acetic acid; In ethanol; for 4h;Reflux; General procedure: Indole-3-aldehyde 16 (1 mmol) and the correspondingalkyl/aryl acid hydrazide 17 (1.05 mmol) were refluxed in ethanol (5 mL) in the presence of glacial acetic acid(0.3 mL) for 4 h. On cooling the reaction mixture to roomtemperature, the crude product was precipitated, filteredand dried. Further recrystallization of the crude products inethanol allowed to obtain pure products in 85-95 % yields.
  • 78
  • [ 536-40-3 ]
  • [ 75629-57-1 ]
  • N'-((1-(4-chlorobenzyl)-1H-indol-3-yl)methylene)-4-chlorobenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With acetic acid In ethanol for 4h; Reflux; General procedure for the synthesis of N'-((1-(substituted)-1H-indol-3-yl)methylene)hydrazides (18a-v) General procedure: Indole-3-aldehyde 16 (1 mmol) and the correspondingalkyl/aryl acid hydrazide 17 (1.05 mmol) were refluxed in ethanol (5 mL) in the presence of glacial acetic acid(0.3 mL) for 4 h. On cooling the reaction mixture to roomtemperature, the crude product was precipitated, filteredand dried. Further recrystallization of the crude products inethanol allowed to obtain pure products in 85-95 % yields.
  • 79
  • 4-benzyloxy-3-methoxy-benzoic acid hydrazide [ No CAS ]
  • [ 75629-57-1 ]
  • N'-((1-(4-chlorobenzyl)-1H-indol-3-yl)methylene)-4-(benzyloxy)-3-methoxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With acetic acid In ethanol for 4h; Reflux; General procedure for the synthesis of N'-((1-(substituted)-1H-indol-3-yl)methylene)hydrazides (18a-v) General procedure: Indole-3-aldehyde 16 (1 mmol) and the correspondingalkyl/aryl acid hydrazide 17 (1.05 mmol) were refluxed in ethanol (5 mL) in the presence of glacial acetic acid(0.3 mL) for 4 h. On cooling the reaction mixture to roomtemperature, the crude product was precipitated, filteredand dried. Further recrystallization of the crude products inethanol allowed to obtain pure products in 85-95 % yields.
  • 80
  • [ 3291-03-0 ]
  • [ 75629-57-1 ]
  • N'-((1-(4-chlorobenzyl)-1H-indol-3-yl)methylene)-3,4,5-trimethoxybenzohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With acetic acid In ethanol for 4h; Reflux; General procedure for the synthesis of N'-((1-(substituted)-1H-indol-3-yl)methylene)hydrazides (18a-v) General procedure: Indole-3-aldehyde 16 (1 mmol) and the correspondingalkyl/aryl acid hydrazide 17 (1.05 mmol) were refluxed in ethanol (5 mL) in the presence of glacial acetic acid(0.3 mL) for 4 h. On cooling the reaction mixture to roomtemperature, the crude product was precipitated, filteredand dried. Further recrystallization of the crude products inethanol allowed to obtain pure products in 85-95 % yields.
  • 81
  • [ 75629-57-1 ]
  • [ 3815-30-3 ]
  • (1E,4E)-1-(1-(4-chlorobenzyl)-1H-indol-3-yl)-5-(4-methoxyphenyl)penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
74.8% With sodium hydroxide In ethanol; water at 0 - 20℃; 4.2.6. General procedure for the synthesis of 9a-s General procedure: To a stirred solution of chalcone 8a-f (0.5 mmol) in ethanol(3 mL) was added 15% aqueous NaOH (1 mL) solution and aldehyde5 (0.5 mmol) at 0° C. The resulting solution was stirred at roomtemperature till the completion of the reaction. The reactionmixture was evaporated to dryness, extracted twice with ethylacetate, the combined organic layers were dried over anhydrousNa2SO4 and concentrated under reduced pressure. The crude masswas purified by column chromatography (Silica gel, 60-120 mesh,8:2 hexane/ethyl acetate) to give the pure product 9a-s.
  • 82
  • [ 42811-79-0 ]
  • [ 75629-57-1 ]
  • (1E,4E)-1-(1-(4-chlorobenzyl)-1H-indol-3-yl)-5-(2,4,6-trimethoxyphenyl)penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.4% With sodium hydroxide In ethanol; water at 0 - 20℃; 4.2.6. General procedure for the synthesis of 9a-s General procedure: To a stirred solution of chalcone 8a-f (0.5 mmol) in ethanol(3 mL) was added 15% aqueous NaOH (1 mL) solution and aldehyde5 (0.5 mmol) at 0° C. The resulting solution was stirred at roomtemperature till the completion of the reaction. The reactionmixture was evaporated to dryness, extracted twice with ethylacetate, the combined organic layers were dried over anhydrousNa2SO4 and concentrated under reduced pressure. The crude masswas purified by column chromatography (Silica gel, 60-120 mesh,8:2 hexane/ethyl acetate) to give the pure product 9a-s.
  • 83
  • [ 5055-37-8 ]
  • [ 75629-57-1 ]
  • N'-((1H-indol-3-yl)methylene)-2-(1-(4-chlorobenzyl)-1H-indol-3-yl)-2-oxoacetohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% In ethanol for 6h; Reflux; 4.1.4. General procedure for the synthesis of bis(indolyl)ketohydrazide-hydrazones (21a-o) and indolyl ketohydrazidehydrazones(23a-e) General procedure: A mixture of glyoxalylhydrazide 18 (1.47mmol) and aldehyde 20 or 22 (1.47mmol) in ethanol (5mL) was refluxed for 6h. After completion of the reaction, ethanol was distilled off and the residue was taken into water (10mL) and allowed to stir at room temperature for 30min. The obtained suspension was filtered, washed with water and dried to obtain yellow solid ketohydrazide-hydrazones 21a-o and 23a-e in 88-96% yields.
  • 84
  • [ 2295-31-0 ]
  • [ 75629-57-1 ]
  • (Z)-5-((1-(4-chlorobenzyl)-1H-indol-3-yl)methylene)thiazolidine-2,4-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.8% With 3-amino propanoic acid In acetic acid for 4h; Reflux; General Procedure for the Preparation of 5a-5i. General procedure: The 3 mmol of appropriate aldehyde (3a-3i, 1) was refluxed with 6 mmol of thiazolidine-2,4-dione (4) in the presence of 6 mmol β-alanine taking acetic acid as solvent for 4 hours. Precipitates obtained were then collected over vacuum filteration, and washed with acetic acid, water and diethyl ether and then dried.
  • 85
  • [ 21414-00-6 ]
  • [ 75629-57-1 ]
  • C26H28ClN3OS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With piperidine In ethanol at 80℃; for 2h; 1.B preparation of 5-((1-(4-chlorophenyl)-1H-indol-3-yl)methylene)-3-(3-(diethylamino)propyl)2-thiazolidin-4-one A solution of 22-thio- (3- (diethylamino) propyl) -4-thiazolidinone2.46 g (0.01 mol) was added to 15 mL of ethanol and then added sequentially4-chlorophenyl-1H-indole-3-methyl 2.69 (0.01 mol)Piperidine 0.85 g (0.01 mol), heated to 80 ° C for 2 h,Reaction complete, cooling, precipitation of solid, filter, filter cake with a small amount of ethanol washing, drying, yellow solid 2.5g,Yield 51%.
  • 86
  • [ 58588-90-2 ]
  • [ 75629-57-1 ]
  • 4-((1-(4-chlorobenzyl)-1H-indol-3-yl)(hydroxy)methyl)-3-methylenedihydrofuran-2(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.77% With ammonium chloride; zinc In tetrahydrofuran; water at 20℃; for 4h; 4.3.4. Synthesis of compounds 1a~1f with 4-((1-benzyl-1H-indol-3-yl) (hydroxy)methyl) -3-methylenedihydrofuran-2(3H)-one (1a)as a sample General procedure: Compound 6 (541.63 mg, 3.06 mmol) mixed with a solution ofintermediate compound 4a (600 mg, 2.55 mmol) and Zn powder(833.62 mg, 12.75 mmol) in THF. And then, a saturated aqueoussolution of ammonium chloride was added dropwise from a constantpressure low liquid funnel. The reaction mixture was stirredat room temperature for 4 h. After suction filtration, THF wasevaporated under reduced pressure. EtOAc (100 mL) was added,and the resulting solution was washed with brine water(3 x 50 mL). The organic phase was dried over Na2SO4, filtered, andconcentrated. The product was purified on a silica gel columneluting with EtOAc, to give compound 1a as a white solid in 85.8%yield.
72.9% With ammonium chloride; zinc In tetrahydrofuran at 20℃; for 4h; 7 Example 7 Preparation of a derivative (I-2) represented by the general formula (I) At room temperature, compound V (0.177 g, 1 mmol) was dissolved in a tetrahydrofuran solution. Compound IV-2 (0.323 g, 1.2 mmol) and zinc powder (0.131 g, 2 mmol) were added. Then saturated ammonium chloride solution (0.35 mL) was added dropwise. After the addition was complete, stir at room temperature for 4h. Diatomaceous earth was suction filtered, the filtrate was evaporated under reduced pressure to remove tetrahydrofuran, and then to the reaction system was added 25mL of water, Extraction with dichloromethane (3 x 10 mL). After combining the organic phases, Dried over anhydrous sodium sulfate, filter, the organic solvent was distilled off under reduced pressure, silica gel column chromatography (petroleum ether: ethyl acetate = 4: 1) gave 0.27 g of light yellow solid I-2, yield: 72.9%
  • 87
  • [ 487-89-8 ]
  • [ 75629-57-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: Indole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 1-chloro-4-(halomethyl)benzene In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere; 2.1 The preparation of compound a1-a23 and b1-b35 General procedure: General operating procedure: To a suspension of dry NaH (240 mg, 10 mmol, 2 equiv) in DMF (10ml) with stirring was added with pyrrole-2-carboxyaldehyde or indole-carboxyaldehyde (5 mmol, 1 equiv) under Nitrogen at 0 °C. After 20 minutes, the reaction mixture was added with alkyl halide (6mmol, 1.2 equiv). The reaction was slowly warmed up to room temperature stirred for 30 minutes. TLC analysis (25% ethyl acetate in petroleum ether) showed no starting material. The reaction mixture was diluted with dichloromethane and washed three times with water, once with brine. The organic solution was dried over Na2SO4, filtered and concentrated. The solvent was removed under reduced pressure to afford the title compound a1-a23 and b1-b35. The residue was directly used for subsequent reaction.
  • 88
  • [ 75629-57-1 ]
  • [ 519-02-8 ]
  • 14-[N-(4-chlorobenzyl)-3-indolemethylenyl]matrine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: (+)-matrine With sodium hydride In tetrahydrofuran at 37℃; for 1h; Stage #2: oncrasin-1 In tetrahydrofuran for 36h; Reflux; 2.2 General procedures for the synthesis of compounds A1-A23 General procedure: General operating procedure: matrine(1.24g, 5 mmol) and 60% sodium hydride (2.4g, 100 mmol) into a round-bottomed flask (100 mL) were resolved in anhydrous tetrahydrofuran (50 mL). The solution was stirred at 37 °C and stirred for 1 h. And then N-substituted pyrrole-2-carboxyaldehyde (6 mmol) was added and the solution was then refluxed for 24 h. After cooling to room temperature, the mixture was poured into water slowly (50 mL), and extracted with dichloromethane (3 × 40 mL). The solvent was removed in vacuo and dried with anhydrous Na2SO4. The residue was purified by flash silica gel column chromatography (petroleum ether/ ethyl acetate, 30%) to afford A1-A23. The yields of the derivatives (A1-A23) were 25-54%.
  • 89
  • [ 99-90-1 ]
  • [ 75629-57-1 ]
  • C24H17BrClNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With piperidine In methanol at 50℃; 4.2.2. Synthesis of variedly substituted (E)-3-(1-benzyl-1H-indol-3-yl)-1-(4-bromophenyl)prop-2-en-1-one (5a-i) General procedure: To a solution of N-substituted indole-3-carbaldehyde, 3a-i(0.23 g, 10 mmol) and 40-bromoacetophenone (4) (0.2 g, 10 mmol)in methanol (10 ml), few drops of piperidine were added. The reactionmixture was stirred for 2 h at 50 C and then left overnight inrefrigerator. The reaction mixture was neutralized with dilutedhydrochloric acid (1:1) and the solid formed was filtered off,washed with water, air dried and recrystallized from absoluteethanol (5a-i).
  • 90
  • [ 1122-54-9 ]
  • [ 75629-57-1 ]
  • C23H17ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With piperidine In ethanol for 24h; Reflux; Synthesis of indolylchalcones (9a-m) General procedure: A solution of indol-3-aldehyde 8 (1 mmol) and appropriate acetophenone (1 mmol) in ethanol (25 mL) was refluxed in the presence of piperidine (0.5 mL) for 24 h. After completion of reaction as confirmed by TLC, the mixture was poured into crushed ice (20 g), neutralized with acetic acid. Obtained solid was filtered, washed with cold water (20 mL) and dried and recrystallized from ethanol to obtain pure indolylchalcones 9a-m in 60-70% yields.
  • 91
  • [ 75629-57-1 ]
  • [ 6882-68-4 ]
  • 14-[N-(4-chlorobenzyl)-1H-indo-3-ylmethylene]sophoridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% General procedure: A 100mL round-bottomed flask was charged with <strong>[6882-68-4]sophoridine</strong> (1.24g, 5mmol), NaH (2.4g, 100mmol) and anhydrous tetrahydrofuran (50mL). The solution was stirred at room temperature for 1h followed by addition of N-substituted indole-carboxyaldehyde (5mmol) and then refluxed for 48h. The reaction mixture was cooled and then poured into water slowly (100mL). It was then extracted with dichloromethane (3×40mL). The combined phases were dried with anhydrous Na2SO4 and concentrated to obtain crude product. The residue was purified by silica gel flash column chromatography (methanol/dichloromethane, 2%) to afford 5a-5y in 24%-53% yields.
  • 92
  • [ 75629-57-1 ]
  • 12-(4-chlorobenzyl)-6,12,12a,12b-tetrahydro-5H-naphtho[2,3-a]carbazole-5,13(5aH)-dione [ No CAS ]
  • (5aS,12aS,12bS)-12-(4-chlorobenzyl)-6,12,12a,12b-tetrahydro-5H-naphtho[2,3-a]carbazole-5,13(5aH)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -30 °C / Inert atmosphere 1.2: 1 h / -30 °C / Inert atmosphere 2.1: C100H112MgO8P2 / methyl cyclohexane / -25 °C / Molecular sieve; Inert atmosphere
  • 93
  • [ 75629-57-1 ]
  • C27H20ClNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -30 °C / Inert atmosphere 1.2: 1 h / -30 °C / Inert atmosphere 2.1: 2C50H56O4P(1-)*Mg(2+) / methyl cyclohexane / -25 °C / Molecular sieve; Inert atmosphere
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