Name: 22948-94-3|1-Acetyl-1H-indole-3-carbaldehyde|98%
Brand: Ambeed
SKU: A325996
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1
[ 22948-94-3 ]
[ 141-82-2 ]
[ 1204-06-4 ]

Reference： [1]Journal of the Chemical Society,1957,p. 1442

2
[ 22948-94-3 ]
[ 141-82-2 ]
[ 75629-64-0 ]
[ 1204-06-4 ]

Reference： [1]Journal of Organic Chemistry,1958,vol. 23,p. 1171,1176

3
[ 22948-94-3 ]
[ 99842-79-2 ]

Yield	Reaction Conditions	Operation in experiment
36%	With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 1.16667h; Inert atmosphere;	Procedure for the synthesis of 1-(3-(hydroxymethyl)-1H-indol-1-yl)ethanone (12)³ 1-Acetyl-1H-indole-3-carbaldehyde (0.5 g, 1.9 mmol) and NaBH4 (0.14 g, 3.7 mmol) were added to dry THF (20 mL), and the reaction was stirred at room temperature under a nitrogen atmosphere for 70 mins. Upon completion by TLC, the reaction was quenched with saturated NH4Cl (5 mL), and the solvent was removed in vacuo. The reaction was extracted with ethyl acetate (2 × 5 mL), and the combined organic layers were washed with water (10 mL). The organic layer was then dried (MgSO4), filtered, and the solvent was removed in vacuo. The product was purified by flash column chromatography on silica gel (1:5 petroleum ether: ethyl acetate) to yield the title compound as a light orange-brown powder (0.18 g, 36% yield). M.p. 134 - 135 oC; Rf = 0.50 (1:5 petroleum ether: ethyl acetate); 1H NMR (300 MHz, d6-DMSO): δH = 8.31 (1 H, d, J = 8.0 Hz, Ar), 7.71 (1 H, s, Ar), 7.69 - 7.62 (1 H, m, Ar), 7.36-7.22 (2 H, m, Ar), 5.16 (1 H, t, J = 5.5 Hz, OH), 4.65 (2 H, dd, J = 5.5, 1.0 Hz, CH2), 2.62 (3 H, s, CH3); 13C NMR (75 MHz, d6-DMSO): δC = 169.37 (C=O), 135.42 (Ar, Cq), 129.40 (Ar, Cq), 124.77 (Ar, CH), 123.93 (Ar, CH), 123.17 (Ar, CH), 122.64 (Ar, Cq), 119.70 (Ar, CH), 115.92 (Ar, CH), 55.20 (CH2), 23.86 (CH3); IR (neat, cm-1) ν = 3501 (free O-H stretch, sharp), 1684 (C=O stretch), 1007 (C-O stretch); MS (EI): m/z 130 ([M-OH-Ac]-, 100%), 147 ([M-Ac]-, 43%); HRMS found: [M+H]+ 190.0862, C11H11NO2+H+ requires 190.0863.
	With tetrahydrofuran; lithium borate

Reference： [1]Sherer, Christopher; Tolaymat, Ibrahim; Rowther, Farzana; Warr, Tracy; Snape, Timothy J. [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 7, p. 1561 - 1565]
[2]Ames et al. [Journal of the Chemical Society, 1956, p. 1984,1988]

4
[ 487-89-8 ]
[ 108-24-7 ]
[ 22948-94-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;
98%	With pyridine for 1.5h;
98%	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 3h;	1-Acetyl-1H-indole-3-carbaldehyde (2): To an ice-cold stirred solution of 1H-indole-3-carbaldehyde (630 mg, 4.34 mmol, 1.0 equiv), DMAP (53 mg, 0.43 mmol, 0.1 equiv), and Et3N (1.51 mL, 10.9 mmol, 2.5 equiv) in dry DCM (30 mL) was slowly added Ac2O (0.61 mL, 6.51 mmol, 1.5 equiv), and the resulting mixture was stirred at room temperature for 3 h. After complete conversion, the reaction was concentrated under reduced pressure to give a beige solid, which was purified by column chromatography (PE:EtOAc = 1:1) to yield acetamide 2 as a white solid (795 mg, 98%). m.p. 165.7-167.5 oC; 1H NMR (500 MHz, CDCl3) δ 10.13 (s, 1H, -CHO), 8.41 (d, J = 10 Hz, 1H), 8.28 (d, J= 10 Hz, 1H), 8.08 (s, 1H), 7.49-7.42 (m, 2H), 2.76 (s, 3H); 13C NMR (125 MHz, CDCl3) δ 185.62, 168.57, 136.38, 135.19, 126.87, 126.06, 125.42, 122.66, 121.91, 116.41, 23.90; HRMS (ESI) m/z calcd for C11H9NO2 [M+H]+ 188.0706, found 188.0705.

91%	With dmap; triethylamine In dichloromethane for 24h; Ambient temperature;
91%	With dmap In tetrahydrofuran at 0 - 20℃; for 1h;	1-Acetylindole-3-carboxaldehyde (14). To a solution of indole-3-carboxaldehyde (13; 2.90g, 20.0 mmol) in THF (66 mL) at 0 C was added Ac2O (6.12 g, 5.6 mL, 60.0 mmol) andcatalytic amount of DMAP. The reaction mixture was stirred for 1 h at rt. After the reactionwas finished, THF was evaporated. The residue was dissolved in CH2Cl2 (120 ml) and thesolution washed with 5% solution of KOH (100 mL), 1M HCl (100 ml) and H2O (80 ml). Afterdrying over anhydrous Na2SO4 and evaporation of solvent, aldehyde 14 was obtained by crystallization from the hot EtOH. Yield: 3.42 g (91%), bright yellow crystals, Rf 0.47 (nhexane/Me2CO 2:1), m.p. 165-166 C (hot ethanol), lit.35 167-169 C (n-hexane/EtOAc).Spectral and analytical data are consistent with literature values.35
91%	With dmap In tetrahydrofuran at 0 - 20℃; for 1h;	To a solution of indole-3-carboxaldehyde (13; 2.90 g, 20.0 mmol) in THF (66 mL) at 0 C was added Ac2O (6.12 g, 5.6 mL, 60.0 mmol) and catalytic amount of DMAP. The reaction mixture was stirred for 1 h at rt. After the reaction was finished, THF was evaporated. The residue was dissolved in CH2Cl2 (120 ml) and the solution washed with 5% solution of KOH (100 mL), 1M HCl (100 ml) and H2O (80 ml). After drying over anhydrous Na2SO4 and evaporation of solvent, aldehyde 14 was obtained by crystallization from the hot EtOH. Yield: 3.42 g (91%), bright yellow crystals, Rf 0.47 (n-hexane/Me2CO 2:1), m.p. 165-166 C (hot ethanol), lit.35 167-169 C (n-hexane/EtOAc). Spectral and analytical data are consistent with literature values.
87%	With dmap; triethylamine In dichloromethane at 20 - 25℃; for 3h; Cooling with ice;
77%	With pyridine; dmap In dichloromethane at 20℃; for 2h;	271.1 Example 271 : Synthesis of (1E,6E)-1-(1-acetyl-1H-indol-3-yl)-7-(4-hydroxyphenyl)hepta-1,6-diene-3,5-dione (CU398); (1) Synthesis of 1-acetyl-1H-indole-3-carboxaldehyde; To a solution of 1H-indole-3-carboxaldehyde (300 mg, 2.07 mmol) in 6.2 mL of dry dichloromethane were added pyridine (0.34 mL, 4.2 mmol), acetic anhydride (0.59 mL, 6.2 mmol), and N,N-dimethylaminopyridine (20 mg, 0.16 mmol) at room temperature, successively. After being stirred at room temperature for 2 h, the reaction mixture was diluted with ethyl acetate. The solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, dried over MgSO4, filtered, and concentrated in vacuo. The resulting solid was rinsed with diethyl ether/hexane to obtain the title compound as a white powder (235 mg, 77%).
	Stage #1: Indole-3-carboxaldehyde With sodium hydride In toluene for 1h; Stage #2: acetic anhydride In toluene for 168h;
	With triethylamine In dichloromethane Heating;
	With triethylamine In dichloromethane Reflux;
	With triethylamine for 3h; Reflux;

Reference： [1]Onodera, Kou; Suzuki, Yumiko; Takashima, Ryo [Organic Letters, 2021, vol. 23, # 11, p. 4197 - 4202]
[2]Location in patent: experimental part Pedras, M. Soledade C.; Okinyo-Owiti, Denis P.; Thoms, Ken; Adio, Adewale M. [Phytochemistry, 2009, vol. 70, # 9, p. 1129 - 1138]
[3]Dai, Jiangkun; Dan, Wenjia; Li, Na; Wang, Junru [European Journal of Medicinal Chemistry, 2018, vol. 157, p. 333 - 338]
[4]Nickisch, Klaus; Klose, Walter; Bohlmann, Ferdinand [Chemische Berichte, 1980, vol. 113, # 5, p. 2036 - 2037]
[5]Budovská, Mariana; Pilátová, Martina Bago; Tischlerová, Viera; Mojžiš, Ján [Arkivoc, 2016, vol. 2016, p. 198 - 234]
[6]Budovská, Mariana; Pilátová, Martina Bago; Tischlerová, Viera; Mojžiš, Ján [Arkivoc, 2016, vol. 2016, # 6, p. 198 - 234]
[7]Bosset, Cyril; Angibaud, Patrick; Stanfield, Ian; Meerpoel, Lieven; Berthelot, Didier; Guérinot, Amandine; Cossy, Janine [Journal of Organic Chemistry, 2015, vol. 80, # 24, p. 12509 - 12525]
[8]Current Patent Assignee: NATIONAL UNIVERSITY CORPORATION TOKYO INSTITUTE OF TECHNOLOGY; KYOTO UNIVERSITY - EP2123637, 2009, A1 Location in patent: Page/Page column 72-73
[9]Maya, Ana B. S.; Pérez-Melero, Concepción; Mateo, Carmen; Alonso, Dulce; Fernández, José Luis; Gajate, Consuelo; Mollinedo, Faustino; Peláez, Rafael; Caballero, Esther; Medarde, Manuel [Journal of Medicinal Chemistry, 2005, vol. 48, # 2, p. 556 - 568]
[10]Sonar, Vijayakumar N.; Thirupathi Reddy; Sekhar, Konjeti R.; Sasi, Soumya; Freeman, Michael L.; Crooks, Peter A. [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 24, p. 6821 - 6824]
[11]Madadi, Nikhil Reddy; Penthala, Narsimha Reddy; Brents, Lisa K.; Ford, Benjamin M.; Prather, Paul L.; Crooks, Peter A. [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 7, p. 2019 - 2021]
[12]Monakhova, Natalia; Korduláková, Jana; Vocat, Anthony; Egorova, Anna; Lepioshkin, Alexander; Salina, Elena G.; Nosek, Jozef; Repková, Eva; Zemanová, Júlia; Jurdáková, Helena; Górová, Renáta; Roh, Jaroslav; Degiacomi, Giulia; Sammartino, José Camilla; Pasca, Maria Rosalia; Cole, Stewart T.; Mikušová, Katarína; Makarov, Vadim [ACS Infectious Diseases, 2021, vol. 7, # 1, p. 88 - 100]

5
[ 22948-94-3 ]
[ 16800-68-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 5℃; for 24h;

Reference： [1]Bourlot; Desarbre; Merour [Synthesis, 1994, # 4, p. 411 - 416]

6
[ 487-89-8 ]
[ 75-36-5 ]
[ 22948-94-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydroxide; tetrabutylammonium hydrogensulfate In dichloromethane Heating;
98%	With triethylamine In dichloromethane for 1h; Heating;
90%	With sodium hydroxide; tetrabutylammonium hydrogensulfate In dichloromethane

40%	Stage #1: 1H-indole-3-carboxaldehyde With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: acetyl chloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h;
	With triethylamine In tetrahydrofuran at 20℃; for 3h;	2.1 N-Acylation of indole-3-carboxaldehyde (I) with 13 acetylchloride in the presence of 14 triethylamine gives 15 1-(acetyl)-3-indole carboxaldehyde (II). 13 Acetyl chloride (2.5mmol) in 10mL of 17 tetrahydrofuran (THF) was added dropwise into the well stirred solution of 11 indole-3-carboxaldehyde (2mmol) and 14 triethylamine (2.5mmol) in 10mL of THF. The reaction mixture was stirred at room temperature for about 3h. After the completion of reaction, the reaction mass was quenched in ice-cold 18 water and the product was extracted in 19 diethyl ether. The ether layer was washed with 5% NaHCO3 followed by distilled water. The solid product 15 1-(acetyl)-3-indole carboxaldehyde (II) was obtained by drying the ether layer over anhydrous Na2SO4. The synthesised compound was characterised by elemental analysis and spectroscopic techniques.

Reference： [1]Reimann; Erdle [Pharmazie, 2000, vol. 55, # 12, p. 907 - 912]
[2]Ottoni, Olivia; Cruz, Rosimeire; Alves, Robledo [Tetrahedron, 1998, vol. 54, # 46, p. 13915 - 13928]
[3]Reimann; Hassler [Pharmazie, 1996, vol. 51, # 8, p. 537 - 540]
[4]Wei, Cunbo; Wu, Jiawen; Zhang, Lizhu; Xia, Zhonghua [Organic Letters, 2022, vol. 24, # 25, p. 4689 - 4693]
[5]Durgadevi; Arjunan; Thirunarayanan; Marchewka; Mohan [Journal of Molecular Structure, 2018, vol. 1164, p. 57 - 69]

7
[ 22948-94-3 ]
[ 122-51-0 ]
[ 21777-14-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With ammonium nitrate In ethanol at 80℃; for 1.5h;

Reference： [1]Reimann; Hassler [Pharmazie, 1996, vol. 51, # 8, p. 537 - 540]

8
[ 22948-94-3 ]
[ 31676-46-7 ]
[ 79240-55-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 23% 2: 72%	With hydrogen In ethanol for 3h; Ambient temperature;

Reference： [1]Reimann; Hassler [Pharmazie, 1996, vol. 51, # 8, p. 537 - 540]

9
[ 22948-94-3 ]
[ 105170-27-2 ]
[ 325796-84-7 ]
[ 325796-74-5 ]

Reference： [1]Pharmazie,2000,vol. 55,p. 907 - 912

10
[ 22948-94-3 ]
[ 487-89-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With polymer-supported potassium thiophenolate In tetrahydrofuran; methanol at 20℃; for 3h;

Reference： [1]MacCoss, Rachel N.; Henry, Dara J.; Brain, Christopher T.; Ley, Steven V. [Synlett, 2004, # 4, p. 675 - 678]

11
[ 22948-94-3 ]
[ 61240-20-8 ]
[ 845624-83-1 ]
[ 845625-15-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 56% 2: 17%	Stage #1: triphenyl-(3,4,5-trimethoxybenzyl)phosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at -15℃; for 0.5h; Stage #2: 1-acetyl-3-indolylcarbaldehyde In tetrahydrofuran; hexane at -15 - 20℃;

Reference： [1]Maya, Ana B. S.; Pérez-Melero, Concepción; Mateo, Carmen; Alonso, Dulce; Fernández, José Luis; Gajate, Consuelo; Mollinedo, Faustino; Peláez, Rafael; Caballero, Esther; Medarde, Manuel [Journal of Medicinal Chemistry, 2005, vol. 48, # 2, p. 556 - 568]

12
[ 22948-94-3 ]
[ 1078-28-0 ]
[ 141-43-5 ]
2-[2-(1-acetyl-1<i>H</i>-indol-3-yl)-vinyl]-1-(2-amino-ethyl)-6-methoxy-quinolinium [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 6331 - 6335

13
[ 3612-20-2 ]
[ 22948-94-3 ]
1-Benzyl-3-[1-(1H-indol-3-yl)-meth-(E)-ylidene]-piperidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With piperidine In methanol at 20 - 50℃;

Reference： [1]Andreani; Cavalli; Granaiola; Guardigli; Leoni; Locatelli; Morigi; Rambaldi; Recanatini; Roda [Journal of Medicinal Chemistry, 2001, vol. 44, # 23, p. 4011 - 4014]

14
(1SR,4RS,5SR,6SR)-4,5,6-tris-[triethylsilyl]oxy}cyclohex-2-ene-1-amine [ No CAS ]
[ 22948-94-3 ]
(1SR,4RS,5SR,6SR)-N-[(1-acetyl-1H-indol-3-yl)methyl]-4,5,6-tris[(triethylsilyl)oxy]cyclohex-2-ene-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃;

Reference： [1]Lysek, Robert; Schuetz, Catherine; Favre, Sylvain; O'Sullivan, Anthony C.; Pillonel, Christian; Kruelle, Thomas; Jung, Pierre M.J.; Clotet-Codina, Imma; Este, Jose A.; Vogel, Pierre [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 18, p. 6255 - 6282]

15
[ 22948-94-3 ]
[ 13431-34-0 ]
C₁₄H₁₆N₄OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrogenchloride In water at 20℃;

Reference： [1]Amoedo, Adriana; Adrio, Luis A.; Antelo, Jose M.; Martinez, Javier; Pereira, M. Teresa; Fernandez, Alberto; Vila, Jose M. [European Journal of Inorganic Chemistry, 2006, # 15, p. 3016 - 3021]

16
[ 22948-94-3 ]
[ 79-19-6 ]
C₁₂H₁₂N₄OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrogenchloride In water at 20℃; for 4h;

Reference： [1]Amoedo, Adriana; Adrio, Luis A.; Antelo, Jose M.; Martinez, Javier; Pereira, M. Teresa; Fernandez, Alberto; Vila, Jose M. [European Journal of Inorganic Chemistry, 2006, # 15, p. 3016 - 3021]

17
[ 22948-94-3 ]
[ 6610-29-3 ]
C₁₃H₁₄N₄OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogenchloride In water at 20℃;

Reference： [1]Amoedo, Adriana; Adrio, Luis A.; Antelo, Jose M.; Martinez, Javier; Pereira, M. Teresa; Fernandez, Alberto; Vila, Jose M. [European Journal of Inorganic Chemistry, 2006, # 15, p. 3016 - 3021]

18
[ 645400-45-9 ]
[ 22948-94-3 ]
N-[(1-acetyl-1H-indol-3-yl)methyl]-N'-(6-methoxy-4-methylquinolin-2-yl)cyclohexane-1,3-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium cyanoborohydride; acetic acid In methanol; dichloromethane for 24h;	49 To a stirred solution of N-(6-methoxy-4-methylquinolin-2-yl) cyclohexane-1, 3-diamine (0.526 mmol, 0.150 g) and [1-ACETYL-LH-INDOLE-3-CARBALDEHYDE] (0.53 mmol, 0.098 g) in [CH2CL2/MEOH] 2: 1 containing 1% [HOAC] (5 mL), [SODIUM CYANOBOROHYDRIDE] (0.89 mmol, 0.056 g) was added. After 24 h, the mixture was concentrated and purified by flash chromatography, to give 0.119 g (50%) of the major diastereomer of the title compound. ['H] NMR (400 MHz, CDC13) 8 8.43 (d, J = 8.1 Hz, 1H), 7.61-7. 57 (m, 2H), 7.37-7. 26 [(M,] 3H), 7.19 (dd, [J=] 9.1, 2.8 Hz, [1H),] 7.06 (d, [J=] 12.8 Hz, 1H), 6.42 (s, 1H), 4. 88 (br, 1H), 4.04-3. 95 [(M,] 3H), 3.86 (s, 3H), 2.82 [(M,] [1H),] 2.58 (s, [3H),] 2.48 (s, 3H), 2.44-2. 38 [(M,] 1H), 2.11-1. 82 [(M,] 4H), 1. [52-1.] 11 [(M,] 4H); [13C NMR (101 MHZ, CDC13) 8168.] 6,155. 0, 154.7, 144.0, 143.5, [136.] 2,130. 0,127. 9,125. 4,124. 1,123. 7,122. 7,121. 9,120. 0,119. 0, 116.8, 112.1, 103.8, 55.7 (2C), 48.7, 42.1, 40.1, 33.1, 32.8, 24.1, 22.4, 19.1 ; LC-MS [M+H] + 457.3. A minor diastereomer was isolated and further purified by [HPLC] (95% 0.1M ammonium acetate buffer: 5% [CH3CN # ] 100% CH3CN, 10 mL/min) to give 0.027 g [(11%)] of the minor diastereomer of the title compound. 1H NMR (500 MHz, CDC13) 8 8.43 (bs, [1H),] [7.] 62 (d, [J=] 7.5 Hz, 1H), 7.57 (d, [J=] 9.1 Hz, 1H), 7.37-7. 25 [(M,] 3H), 7.18 (d, [J=] 8.3 Hz, 1H), 7.07 (s, 1H), 6.50 (s, [1H),] 4.69 (bs, 1H), 4.29 (bs, 1H), 4.01 (d, [J=] 13.6 Hz, 1H), 3.96 (d, J= 13.6 Hz, 1H), 3.88 (s, 3H), 3.03 (bs, 1H), 2.53 (s, [3H),] 2.52 (s, 3H), 1.92-1. 4 [(M,] 9H); LC-MS [[M+H] + 457.] 3.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2004/4726, 2004, A1 Location in patent: Page/Page column 46-47

19
[ 645400-45-9 ]
[ 22948-94-3 ]
N-(6-methoxy-4-methylquinolin-2-yl)-N'-[(1-methyl-1H-indol-3-yl)methyl]cyclohexane-1,3-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With CH₃BN^(1-)H⁽¹⁺⁾H₂NPol; acetic acid In methanol; dichloromethane at 100℃; for 0.166667h;	52 N-(6-methoxy-4-methylquinolin-2-yl)cyclohexane-1,3-diamine (0. [16 MMOL,] 0. 046 g) in [CH2CL2/MEOH 1] : 1 (1. [2 ML), L-METHYLINDOLE-3-CARBOXALDEHYDE (0. 13 MMOL,] 0. 021 g) in CHCl2 (0.6 mL) and [HOAC] (0.060 [ML)] was added to Pol-BH3CN (150 mg, pre-swollen in [CH2C12,] 0.6 mL). The resultant slurry was subjected to microwave heating single node 100 [XB0;C,] 10 min. The resin was filtered and washed with portions (1-2 [ML)] [OF CH2C12 AND] MeOH, and the filtrate was concentrated. The residue was purified on [HPLC] (95% 0.1M ammonium acetate buffer: 5% [CH3CN <] 100% CH3CN, 10 [ML/MIN)] to give 0.021 g (34%) of the title compound as a mixture of diastereomers (-6 : [1).'H] NMR (400 MHz, [MEOH-D4)] 8 7.65 (d, [J= 8.] 1 Hz, [1H,] major isomer), 7.59-7. 55 (m, 1H, minor isomer), 7.54 (d, [J=] 9.1 Hz, 1H, major isomer), 7.37 (d, [J=] 8.3 Hz, [1H,] major isomer), 7.30 (d, [J=] 8.3 Hz, 1H, minor isomer), 7.27 (s, 1H, major isomer), 7.23-7. 07 (m, 5H), 7.01-6. 97 [(M,] 1H, minor isomer), 6.62 (s, 1H, minor isomer), 6.58 (s, 1H, major isomer), 4.36 [(M,] [1H,] minor isomer), 4.20 (s, [2H),] 3.95 (tt, J= 11.4, 3.7 Hz, 1H, major isomer), 3.87 (s, 3H, minor isomer), 3.85 (s, 3H, major isomer), 3.78 (s, 3H, major isomer), 3.59 (s, 3H, minor isomer), 3.21 [(M,] [1H,] minor isomer), 3.07 (tt, [J=] 11.5, 3. [4 HZ,] 1H, major isomer), 2.58-2. 40 [(M,] [1H),] 2.51 (s, 3H, minor isomer), 2.49 (s, 3H, major isomer), 2. [18-1. 19 (M,] 7H); LC-MS [[M+H] +] 429.3.

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2004/4726, 2004, A1 Location in patent: Page/Page column 48

20
[ 22948-94-3 ]
[ 74124-56-4 ]
[ 1115219-70-9 ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 0 - 20℃; for 1h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Kuramochi, Kouji; Aoki, Toshiaki; Nakazaki, Atsuo; Kamisuki, Shinji; Takeno, Masahiro; Ohnishi, Kensuke; Kimoto, Kuniaki; Watanabe, Nobuo; Kamakura, Takashi; Arai, Takao; Sugawara, Fumio; Kobayashi, Susumu [Synthesis, 2008, # 23, p. 3810 - 3818]

21
[ 22948-94-3 ]
[ 2770-11-8 ]
[ 1158910-00-9 ]

Yield	Reaction Conditions	Operation in experiment
78%		A solution of the aniline (250 mg, 1.14 mmol), l-acetyl-3-indolecarboxaldehyde (107 mg, 0.57 mmol), NaBH(OAc)3 (302 mg, 1.43 mmol) and AcOH (205 mg, 3.42 mmol) in 1,2-DCE (3 ml) was stirred at room temperature for 16 h. The reaction was quenched with a saturated aqueous solution of sodium bicarbonate (5 ml) and extracted with EtOAc (3 x 5 ml). The combined organics were dried (MgSO4), filtered and concentrated in vacuo before purification by flash chromatography (eluant; 8:2 hexane:EtOAc to EtOAc) proceeded to afford the desired product which was recrystallised from EtOAc and hexane to afford a cream solid (174.1 mg, 78%).1H NMR: (CDCl3, 270 MHz): delta 2.56 (3H, s, CH3), 3.77 (IH, br s, NH), 4.47 (2H, br s,CH2), 6.65-7.50 (12H, m, ArH), 8.41 ppm (IH, d, J= 7.9 Hz, ArH). 13C NMR: (CDCl3, 67.93 MHz): 5 24.1, 39.7, 112.1, 117.0, 117.6, 118.5, 119.0, 119.6,120.1, 123.0, 123.7, 125.5, 125.7, 128.0, 129.7, 136.1, 140.0, 143.5, 156.2, 168.6 ppm.LCMS: 1.550 min, (95% MeOH : 5% water at 1.0 ml/min), AP": 389.20.HPLC: 3.410 min, 95.90% purity, (isocratic, 90% acetonitrile : 10% water at 1.0 ml/min).HRMS (MicroTOF): C23H20ClN2O2 requires 391.1208, found 391.1194. M.Pt. 107-1080C.

Reference： [1]Patent: WO2009/66072,2009,A2 .Location in patent: Page/Page column 105

22
[ 22948-94-3 ]
[ 1190220-94-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With hydroxylamine hydrochloride; sodium acetate In ethanol; water at 47 - 50℃; for 0.166667h;

Reference： [1]Location in patent: experimental part Pedras, M. Soledade C.; Okinyo-Owiti, Denis P.; Thoms, Ken; Adio, Adewale M. [Phytochemistry, 2009, vol. 70, # 9, p. 1129 - 1138]

23
[ 22948-94-3 ]
methyl (2Z)-2-(bromomethyl)-3-(2-bromophenyl)prop-2-enoate [ No CAS ]
C₂₂H₂₀BrNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With indium In tetrahydrofuran; water at 20℃; for 1h;

Reference： [1]Location in patent: experimental part Kim, Ko Hoon; Kim, Sung Hwan; Park, Bo Ram; Kim, Jae Nyoung [Tetrahedron Letters, 2010, vol. 51, # 26, p. 3368 - 3371]

24
[ 22948-94-3 ]
[ 876-87-9 ]
[ 76384-48-0 ]

Yield	Reaction Conditions	Operation in experiment
	With pyrrolidine at 20 - 80℃;	4 To a 20 mL vial, building block I (0.1 mmol) and II (0.3-0.5 mmol) was dissolved together in 10 mL absolute ethanol. 3 μL pyrrolidine was added to the solution. The condensation reaction was carried out using a heating block at 80° C. for 3 to 6 hours. After the reaction was completed, the mixture stood at room temperature overnight. Purification was carried out by two different methods depending on the compounds. For the crystallized compounds, the crystal was filtered and re-crystallized in ethanol and dried in vacuum. Non-crystallized compounds were purified by silica preparative TLC or column chromatography using methanol:methylene chloride=1:10. (Solvent gradient polarity might be different depending on compounds). All purified compounds were identified by LCMS and an average of 95% purity was determined in 250 nm absorption wavelength. Note that compound E36 was the deacetylated indole product. The structure and purity of the final selected four compounds were confirmed by 1H NMR (400 MHz, Methyl-d3 alcohol-d and Chloroform-d) before detailed cell staining study (Table 1). TABLE 1 Selected Dyes Purification Method and Characterization Dye Purification Method Characterization E36 Deacetylated product 8.64 (d, J = 8.8 Hz, 1H); 8.49 (d, J = purified by ethanol 15.2 Hz, 1H); 8.40 (d, J = 8.8 Hz, 1H); re-crystallization 8.30 (d, J = 8.8 Hz, 1H); 8.15 (d, J = 8.0 Hz, 1H); 8.10 (m, 3H); 7.84 (t, J = 8.0 Hz, 1H); 7.56 (m, 1H); 7.52 (d, J = 15.6 Hz, 1H); 7.39 (m, 2H); 4.52 (s, 3H). LCMS (ESI) m/z for C20H17N2+calcd 285.1 found 285.2 E144 Ethanol 8.75 (d, J = 9.2 Hz, 1H); 8.40 (d, J = re-crystallization. 15.6 Hz, 1H); 8.35 (d, J = 8.8 Hz, 1H); 8.27 (d, J = 8.8 Hz, 1H); 8.21 (dd, J = 1.2, 8.0 Hz, 1H); 8.14 (ddd, J = 0.8, 7.2, 8.8 Hz, 1H); 8.05 (d, J = 16 Hz 1H); 7.88 (dt, J = 0.4 Hz, 7.6 Hz, 1H); 6.31 (s, 2H); 4.49 (s, 3H); 4.04 (s, 6H); 3.95 (s, 3H). LCMS (ESI) m/z for C21H22NO3+ calcd 336.2 found 336.2 F22 Ethanol 8.53 (d, J = 8.8 Hz, 1H); 8.25 (d, J = re-crystallization 9.2 Hz, 1H); 8.16 (d, J = 9.6, 1H); 7.85 (d, J = 15.2 Hz, 1H); 7.79 (d, J = 8.8 Hz, 1H); 7.60 (dd, J = 2.8, 9.6 Hz, 1H); 7.49 (d, J = 15.6 Hz, 1H); 7.36 (d, J = 2.8 Hz, 1H); 6.70 (d, J = 9.2 Hz, 1H); 4.64 (s, 3H); 4.00 (s, 3H); 3.09 (s, 6H). LCMS (ESI) m/z for C21H23N2O+ calcd 319.2 found 319.2 F112 Ethanol 8.665 (d, J = 8.8 Hz, 1H); 8.494 (d, J = re-crystallization 8.8 Hz, 1H); 8.219 (d, J = 9.6 Hz, 1H); 8.188 (d, J = 15.6 Hz, 1H); 8.066 (d, J = 15.6 Hz, 1H); 8.043 (d, J = 9.2 Hz, 1H); 7.714 (dd, J = 2.8, 9.6 Hz, 1H); 7.347 (d, J = 2.8 Hz, 1H); 7.184 (d, J = 2.4 Hz, 1H); 7.091 (dd, J = 2.8, 9.2 Hz, 1H); 4.866 (s, 3H); 4.032 (s, 3H); 3.150 (s, 6H). LCMS (ESI) m/z for C21H22N3O3+ calcd 365.2 found 365.1

Reference： [1]Current Patent Assignee: NEW YORK UNIVERSITY - US7790896, 2010, B2 Location in patent: Page/Page column 11-12

25
[ 22948-94-3 ]
[ 15827-42-6 ]
C₂₀H₂₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With hafnium tetrakis(trifluoromethanesulfonate) In acetonitrile at 20℃; for 14h;

Reference： [1]Location in patent: experimental part Nakamura, Masayuki; Niiyama, Kenji; Yamakawa, Takeru [Tetrahedron Letters, 2009, vol. 50, # 47, p. 6462 - 6465]

26
[ 22948-94-3 ]
[ 34907-02-3 ]
[ 1320256-90-3 ]

Yield	Reaction Conditions	Operation in experiment
34%	With copper(II) bis(trifluoromethanesulfonate); trimethyl orthoformate In dichloromethane at 100℃; for 0.166667h; Inert atmosphere; Microwave irradiation;	General procedure C General procedure: A solution of aldehyde (1 eq), Cu(OTf)2 (0.1 eq), trimethyl orthoformate (1.1 eq) and pyruvicamide (1.2 eq) in dry CH2Cl2 under Argon was heated under microwave irradiation to 100 °C for 10 min. The yellow to brown solution was purified by flash chromatography using cyclohexane/ethyl acetate as eluent.

Reference： [1]Steuer, Christian; Gege, Christian; Fischl, Wolfgang; Heinonen, Karl H.; Bartenschlager, Ralf; Klein, Christian D. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 13, p. 4067 - 4074]

27
[ 141-84-4 ]
[ 22948-94-3 ]
(5Z)-5-((1-acetyl-1H-indol-3-yl)methylene)-2-thioxothiazolidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With ammonium acetate In toluene at 160℃; for 0.0833333h; Microwave irradiation;

Reference： [1]Mendgen, Thomas; Steuer, Christian; Klein, Christian D. [Journal of Medicinal Chemistry, 2012, vol. 55, # 2, p. 743 - 753]

28
[ 1123-55-3 ]
[ 22948-94-3 ]
[ 24850-33-7 ]
[ 1281881-57-9 ]

Reference： [1]Medicinal Chemistry Research,2012,vol. 21,p. 1090 - 1097

29
[ 22948-94-3 ]
[ 79-11-8 ]
[ 306963-82-6 ]
[ 1415679-37-6 ]

Yield	Reaction Conditions	Operation in experiment
30%	With sodium acetate In acetic anhydride; acetic acid	6.1.1.2 Synthesis of 6-substituted thiazolo [3,2-b]-1,2,4-triazole-5(6H)-ones (1a-1o). General procedure: The equimolar amounts of (±)-3-[1-(4-(2-methylpropyl)phenyl)ethyl]-1,2,4-triazole-5-thione (1), the corresponding aldehyde, chloroacetic acid and sodium acetate were added to 6 ml of acetic acid and 8 ml of acetic anhydride. Reaction time was determined by TLC-monitoring the consumption of the starting material. After completion of the reaction, the reaction mixture was poured on ice, and the crude precipitate was filtered and dissolved in dichloromethane and washed with a sodium bicarbonate and saturated sodium chloride solution, respectively. The organic layer was evaporated to dryness and the crude product then recrystallized from methanol [20-22]. The characterization data of synthesized novel 6-substituted thiazolo[3,2-b]-1,2,4-triazole-5(6H)-ones are given in Tables 1-3.

Reference： [1]Uzgören-Baran, Ayşe; Tel, Banu Cahide; Sargöl, Deniz; Öztürk, Elif Inci; Kazkayas, Inci; Okay, Gürol; Ertan, Mevlüt; Tozkoparan, Birsen [European Journal of Medicinal Chemistry, 2012, vol. 57, p. 398 - 406]

30
[ 487-89-8 ]
[ 22948-94-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Jing, Lingling; Wang, Liang; Zhao, Yinglan; Tan, Rui; Xing, Xiumei; Liu, Ting; Huang, Wencai; Luo, Youfu; Li, Zicheng [Journal of Chemical Research, 2012, vol. 36, # 12, p. 691 - 696]

31
[ 99842-79-2 ]
[ 22948-94-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With Iron(III) nitrate nonahydrate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; sodium chloride In 1,2-dichloro-ethane at 20℃; for 1.5h;

Reference： [1]Liu, Jinxian; Ma, Shengming [Organic and Biomolecular Chemistry, 2013, vol. 11, # 25, p. 4186 - 4193]

32
[ 22948-94-3 ]
[ 126-81-8 ]
[ 109-77-3 ]
[ 1573119-74-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	In dimethyl sulfoxide at 20℃; for 3h; Green chemistry;	Synthesis of 4-(1-actyl-1H-indol-3-yl)-2-amino-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile (4i) A mixture of 1-aceyl-1H-indole-3-carbaldehyde (0.5 g, 2.7mmol), malononitrile (0.20 g, 2.9 mmol) and dimedone (0.37 g, 2.7 mmol) in DMSO (7 mL) was stirred at room temperature for 3 h. The resulting mixture was poured into ice, stirred for 15 min, the solid obtained was filtered and washed with water and diethyl ether to afford pure product (0.87 g, 87%) as a light yellow solid. Mp 206-208°C; δH (400 MHz, DMSO-d6) 0.88(s, 3H), 1.04 (s, 3H), 2.10 (d, J = 16.1 Hz, 1H), 2.25 (d, J = 16.1 Hz, 1H), 2.54-2.59 (m, 2H),2.62 (s, 3H), 4.55 (s, 1H), 7.07 (s, 2H), 7.23-7.27 (m, 1H), 7.29-7.33 (m, 1H), 7.41 (d, J = 7.6Hz, 1H), 7.66 (s, 1H), 8.32 (d, J = 8.2 Hz, 1H); δC (100 MHz, DMSO-d6) 24.3, 27.1, 27.5,28.8, 32.1, 50.4, 57.1, 111.6, 116.5, 119.2, 120.1, 123.6, 124.2, 124.6, 125.0, 128.8, 135.9,159.3, 163.1, 169.7, 196.1; Anal. Calcd. For C22H21N3O3: C, 70.38; H, 5.64; N, 11.19. Found:C, 70.43; H, 5.66; N, 11.21%; ESI-m/z calcd for [C22H21N3O3+H]+ 376.1, found 376.1.

Reference： [1]Ponpandian, Thanasekaran; Muthusubramanian, Shanmugam [Synthetic Communications, 2014, vol. 44, # 6, p. 868 - 874]

33
[ 22948-94-3 ]
[ 17403-09-7 ]
1-(3-((4-(1H-indol-3-yl)piperidin-1-yl)methyl)-1H-indol-1-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 4h; Inert atmosphere;	10 4.1.2.6.1. General procedure A General procedure: Aldehyde (1.5 eq.) and amine (1 eq.) were mixed in 1,2-dichloroethane, followed by addition of sodium triacetoxyborohydride (1.4 eq.). The reaction was stirred at room temperature under inert atmosphere for 4 h. The reaction mixture was quenched with sat. aq. NaHCO3, and the product was extracted with ethyl acetate. The organic phasewas dried (Na2SO4),and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography with ethyl acetate/acetonitrile:water:methanol (1:1:1) to afford the desired product.

Reference： [1]Santos, Sofia A.; Lukens, Amanda K.; Coelho, Lis; Nogueira, Fátima; Wirth, Dyann F.; Mazitschek, Ralph; Moreira, Rui; Paulo, Alexandra [European Journal of Medicinal Chemistry, 2015, vol. 102, p. 320 - 333]

34
[ 22948-94-3 ]
[ 109-77-3 ]
2-((1-acetyl-1H-indol-3-yl) methylene) malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With N-(3-trifluoromethylphenylcarbamoyl)chitosan In dimethyl sulfoxide at 20℃; for 72h;	7 2.8. General procedure for Knoevenagel condensation General procedure: To a solution of the aryl aldehyde (1 equiv.) in DMSO (1.5 mL), malononitrile (or ethyl cyanoacetate) (1.1 equiv.) and chitosan beads or ureydil chitosan derivative 1 disks (10-15 units) were added. The heterogeneous mixture was allowed to stand at room temperature until the reaction was completed monitoring by TLC(1:2 or 1:4 EtOAc-hexane). Then, the reaction was diluted with CH2Cl2(3 mL) and the chitosan beads, or compound 1 disks, fil-tered off. The resulting solution was concentrated, treated with H2O(2.5 mL) and extracted with EtOAc (4 × 10 mL). The organic layers were successively washed with H2O (3 × 15 mL) and brine, then dried (Na2SO4) and concentrated to give the desired product.

Reference： [1]Franconetti; Domínguez-Rodríguez; Lara-García; Prado-Gotor; Cabrera-Escribano [Applied Catalysis A: General, 2016, vol. 517, p. 176 - 186]

35
[ 22948-94-3 ]
[ 105-56-6 ]
C₁₆H₁₄N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With N-(3-trifluoromethylphenylcarbamoyl)chitosan In dimethyl sulfoxide at 20℃; for 48h; stereoselective reaction;	7 2.8. General procedure for Knoevenagel condensation General procedure: To a solution of the aryl aldehyde (1 equiv.) in DMSO (1.5 mL), malononitrile (or ethyl cyanoacetate) (1.1 equiv.) and chitosan beads or ureydil chitosan derivative 1 disks (10-15 units) were added. The heterogeneous mixture was allowed to stand at room temperature until the reaction was completed monitoring by TLC(1:2 or 1:4 EtOAc-hexane). Then, the reaction was diluted with CH2Cl2(3 mL) and the chitosan beads, or compound 1 disks, fil-tered off. The resulting solution was concentrated, treated with H2O(2.5 mL) and extracted with EtOAc (4 × 10 mL). The organic layers were successively washed with H2O (3 × 15 mL) and brine, then dried (Na2SO4) and concentrated to give the desired product.

Reference： [1]Franconetti; Domínguez-Rodríguez; Lara-García; Prado-Gotor; Cabrera-Escribano [Applied Catalysis A: General, 2016, vol. 517, p. 176 - 186]

36
[ 22948-94-3 ]
[ 1576-35-8 ]
N'-((1-acetyl-1H-indol-3-yl)methylene)-4-methylbenzenesulfonohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In methanol at 20℃; Inert atmosphere;
	In ethanol at 20℃; for 2h;

Reference： [1]Crespin, Lorène; Biancalana, Lorenzo; Morack, Tobias; Blakemore, David C.; Ley, Steven V. [Organic Letters, 2017, vol. 19, # 5, p. 1084 - 1087]
[2]Panda, Subhankar; Pradhan, Nirmalya; Manna, Debasis [ACS Combinatorial Science, 2018, vol. 20, # 10, p. 573 - 578]

37
[ 22948-94-3 ]
3-amino-2-(3,4-dimethoxybenzyl)quinazolin-4(3H)-one [ No CAS ]
8,9-dimethoxy-11-(1-acetyl-1H-indol-3-yl)-11,12-dihydroquinazolino[3,2-c][2,3]benzodiazepin-14(6H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%	With trifluoroacetic acid for 14h; Reflux;	8,9-Dimethoxy-11-(1-acetyl-1H-indol-3-yl)-11,12-dihydroquinazolino[3,2-c][2,3]benzodiazepin-14(6H)-one(2e, C₂₈H₂₄N₄O₄) A mixture of 0.311 g aminoquinazolone 1 (1 mmol) and 0.187 g 1-acetyl-1H-indole-3-carbaldehyde (1 mmol) in4 cm3 TFA was refluxed for 14 h. After cooling, the reaction mixture was poured into 50 cm3 of ice water, neutralized with 25% aqueous ammonia and left at room temperature for 60 min. The precipitate was filtered off, washed with water and dried. Recrystallization from acetone gave the title ompound as a white solid. Yield: 0.25 g (52%). M.p.: 245-247 °C; 1H NMR (400 MHz, DMSO-d6): d = 8.33 (d,J = 8.0 Hz, 1H, H-7-indole), 8.07 (d, J = 8.0 Hz, 1H, H-1),7.86 (d, J = 8.0 Hz, 1H, H-4-indole), 7.75 (t, J = 8.0 Hz,1H, H-3), 7.61 (d, J = 8.0 Hz, 1H, H-4), 7.55 (s, 1H, H-2-indole), 7.45 (t, J = 8.0 Hz, 1H, H-2), 7.25 (t, J = 8.0 Hz,1H, H-6-indole), 7.14 (t, J = 8.0 Hz, 1H, H-5-indole), 6.94(s, 1H, H-10), 6.77 (s, 1H, NH), 6.50 (s, 1H, H-7), 5.73 (s, 1H,H-11), 5.22 (s, 1H, H-6-a), 3.99 (s, 1H, H-6-b), 3.81 (s, 3H,OCH3-8), 3.52 (s, 3H, OCH3-9), 2.49 (s, 3H, COCH3) ppm;13C NMR (100 MHz, DMSO-d6): d = 170.0, 159.9, 157.9,148.6, 148.3, 147.5, 136.1, 135.0, 129.3, 129.1, 127.5, 126.9,126.5, 125.4, 124.3, 123.8, 122.1, 121.0, 116.5, 114.8, 113.5,59.1, 56.2, 40.9, 24.4 ppm; MS (70 eV): m/z (%) = 480(M+, 82), 463 (26), 437 (17), 421 (10), 353 (12), 334 (77),319 (87), 292 (34), 277 (100), 262 (14), 234 (12), 219 (12),117 (10).

Reference： [1]Tolkunov, Andrey S.; Mazepa, Alexander V.; Palamarchuk, Gennadiy V.; Shishkin, Oleg V.; Sujkov, Sergey Yu.; Bogza, Sergey L. [Monatshefte fur Chemie, 2017, vol. 148, # 4, p. 695 - 701]

38
[ 930-68-7 ]
[ 22948-94-3 ]
(E)-6-((1-acetyl-1H-indol-3-yl)methylene)cyclohexen-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: cyclohexenone With titanium tetrachloride; triphenylphosphine In dichloromethane at -50℃; for 0.25h; Stage #2: 1-acetyl-3-indolylcarbaldehyde In dichloromethane at 20℃;	23 Example 23 (E) -6 - ((1-Acetyl-1H-indol-3-yl) methylene) cyclohexen-2-one Cyclohexene-2-one (0.95 g, 10.0 mmol) was dissolved in 15 ml of anhydrous dichloromethane and added at -50 ° CTo a solution of 200 mg of TiCl4 and PPh3 (2.62 g, 10.0 mmol) over 15 min, 1-acetyl-lH-indole-3-carbaldehyde (3.74 g,20.0 mmol) and reacted overnight at room temperature. After the reaction was complete, 10% K2CO3 solution was added for 10 min, the organic layer was collected,Column chromatography. To give 2.31 g of solid in 87% yield.
62%	With titanium tetrachloride; triphenylphosphine In dichloromethane at -40 - 20℃;	General procedure for preparation of benzylidenecyclohexenoneanalogues (2a-v, 15a, and 15c-e) General procedure: To a solution of the cyclic ketene (5.20 mmol) and PPh3 (1.36 g,5.20 mmol) in 5 mL DCM, was added TiCl4 (6 ml, 5.46 mmol) andaromatic aldehyde (5.72 mmol). The reaction solution was stirredat -40 °C for 0.5h, and continuously stirred at r.t. for 12-24 h. Thenthe mixture was poured into saturated K2CO3 solution andextracted with 50 mL DCM for three times. The combined organiclayers were isolated, dried over MgSO4, concentrated by evaporationin vacuum, and finally purified using column chromatographyof silica gel with EtOAc/hexanes (v:v 1:20-1:5) to afford 2a-v.

Reference： [1]Current Patent Assignee: NANTONG UNIVERSITY - CN106673988, 2017, A Location in patent: Paragraph 0122; 0123
[2]Hsu, Pei-Ling; Lee, Kuo-Hsiung; Li, Yangyang; Ling, Yong; Liu, Ji; Meng, Chi; Morris-Natschke, Susan L.; Qian, Jianqiang; Xu, Zhongyuan; Yang, Yumin; Zhang, Yanan; Zhu, Weizhong [European Journal of Medicinal Chemistry, 2020, vol. 204]

39
[ 22948-94-3 ]
1-acetylindole-3-carboxyaldehyde oxime [ No CAS ]
1-acetylindole-3-carboxyaldehyde oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sodium acetate In tetrahydrofuran; water at 20℃; for 4h; Overall yield = 88 %; Overall yield = 3.26 g;	1-Acetylindole-3-carboxaldehyde oxime (17). To a stirred solution of aldehyde (14; 3.42 g,18.3 mmol) in THF (80 mL) was added a solution of hydroxylammonium chloride (1.98 g,28.5 mmol) and NaOAc (1.72 g, 12.6 mmol) in water (14 mL) and the mixture was stirred for4 h at rt. After evaporation of THF and addition of water (80 mL), the oxime 17 was extractedwith EtOAc (1 × 350 mL, 1 × 250 mL). The extract was dried over Na2SO4 and the residueobtained after evaporation of the solvent was further crystallized from Me2CO/n-hexane toafford oxime 17 as a mixture of E- and Z-isomer.Yield: 3.26 g (88%), white crystals, Rf 0.44 (n-hexane/Me2CO 2:1), m.p. 145-148 C(Me2CO/n-hexane). Anal. Calcd for C11H10N2O2 requires: C, 65.34; H, 4.98; N, 13.85. Found:C, 65.27; H, 4.80; N, 13.51. MS (EI), m/z (%): 203 [M+H]+ (7), 202 [M]+ (66), 160 (100), 43[CH3CO]+ (78). IR (KBr) max: 3229 (OH); 1706 (C=O); 1620 (C=N); 1539; 1433; 1365; 1200;1119; 932; 745 cm-1. 1H NMR (400 MHz, DMSO-d6) 11.64 (bs, 0.3H, OH min.), 10.73 (bs,0.7H, OH maj.), 8.60 (s, 0.3H, CH= min.), 8.40 (d, J 8.2, 1H, H-7), 8.26 (s, 0.7H, CH= maj.),8.14 (d, J 7.6, 1H, H-4), 7.72 (s, 0.3H, H-2 min.), 7.63 (s, 0.7H, H-2 maj.), 7.39-7.34 (m, 1H,H-6), 7.31-7.28 (m, 1H, H-5), 2.67 (s, 0.9H, CH3 min.), 2.64 (s, 2.1H, CH3 maj.). 13C NMR(100 MHz, DMSO-d6) 169.3 (C=O min.), 168.7 (C=O maj.), 143.5 (CH= maj.), 137.3 (C-7amin.), 136.4 (C-7a maj.), 134.8 (CH= min.), 130.3 (C-3a min.), 129.0 (C-2 min.), 127.4 (C-3amaj.), 126.8 (C-2 maj.), 126.1 (C-6 maj.), 125.6 (C-6 min.), 124.3 (C-5), 122.6 (C-4), 118.3(C-7 min.), 116.7 (C-3 maj.), 116.5 (C-7 maj.), 111.7 (C-3 min.), 24.1 (CH3).
	With hydroxylamine hydrochloride; sodium acetate In tetrahydrofuran; water at 20℃; for 4h; Overall yield = 88 %; Overall yield = 3.26 g;	To a stirred solution of aldehyde (14; 3.42 g, 18.3 mmol) in THF (80 mL) was added a solution of hydroxylammonium chloride (1.98 g, 28.5 mmol) and NaOAc (1.72 g, 12.6 mmol) in water (14 mL) and the mixture was stirred for 4 h at rt. After evaporation of THF and addition of water (80 mL), the oxime 17 was extracted with EtOAc (1 × 350 mL, 1 × 250 mL). The extract was dried over Na2SO4 and the residue obtained after evaporation of the solvent was further crystallized from Me2CO/n-hexane to afford oxime 17 as a mixture of E- and Z-isomer. Yield: 3.26 g (88%), white crystals, Rf 0.44 (n-hexane/Me2CO 2:1), m.p. 145-148 C (Me2CO/n-hexane). Anal. Calcd for C11H10N2O2 requires: C, 65.34; H, 4.98; N, 13.85. Found: C, 65.27; H, 4.80; N, 13.51. MS (EI), m/z (%): 203 [M+H]+ (7), 202 [M]+ (66), 160 (100), 43 [CH3CO]+ (78). IR (KBr) max: 3229 (OH); 1706 (C=O); 1620 (C=N); 1539; 1433; 1365; 1200; 1119; 932; 745 cm-1. 1H NMR (400 MHz, DMSO-d6) 11.64 (bs, 0.3H, OH min.), 10.73 (bs, 0.7H, OH maj.), 8.60 (s, 0.3H, CH= min.), 8.40 (d, J 8.2, 1H, H-7), 8.26 (s, 0.7H, CH= maj.), 8.14 (d, J 7.6, 1H, H-4), 7.72 (s, 0.3H, H-2 min.), 7.63 (s, 0.7H, H-2 maj.), 7.39-7.34 (m, 1H, H-6), 7.31-7.28 (m, 1H, H-5), 2.67 (s, 0.9H, CH3 min.), 2.64 (s, 2.1H, CH3 maj.). 13C NMR (100 MHz, DMSO-d6) 169.3 (C=O min.), 168.7 (C=O maj.), 143.5 (CH= maj.), 137.3 (C-7a min.), 136.4 (C-7a maj.), 134.8 (CH= min.), 130.3 (C-3a min.), 129.0 (C-2 min.), 127.4 (C-3a maj.), 126.8 (C-2 maj.), 126.1 (C-6 maj.), 125.6 (C-6 min.), 124.3 (C-5), 122.6 (C-4), 118.3 (C-7 min.), 116.7 (C-3 maj.), 116.5 (C-7 maj.), 111.7 (C-3 min.), 24.1 (CH3).
	With hydroxylamine hydrochloride; sodium hydroxide Milling;

Reference： [1]Budovská, Mariana; Pilátová, Martina Bago; Tischlerová, Viera; Mojžiš, Ján [Arkivoc, 2016, vol. 2016, p. 198 - 234]
[2]Budovská, Mariana; Pilátová, Martina Bago; Tischlerová, Viera; Mojžiš, Ján [Arkivoc, 2016, vol. 2016, # 6, p. 198 - 234]
[3]Baláž, Matej; Kudličková, Zuzana; Vilková, Mária; Imrich, Ján; Balážová, L'udmila; Daneu, Nina [Molecules, 2019, vol. 24, # 18]

40
[ 22948-94-3 ]
[ 1895-39-2 ]
1-(3-(2,2-difluorovinyl)-1H-indol-1-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With triphenylphosphine In N,N-dimethyl-formamide at 110℃; for 2h;
53%	With triphenylphosphine In N,N-dimethyl-formamide at 100℃; for 1h; Inert atmosphere;
	With triphenylphosphine In N,N-dimethyl-formamide at 110℃;

Reference： [1]Liu, Jiawang; Yang, Ji; Ferretti, Francesco; Jackstell, Ralf; Beller, Matthias [Angewandte Chemie - International Edition, 2019, vol. 58, # 14, p. 4690 - 4694][Angew. Chem., 2019, vol. 131, # 14, p. 4738 - 4742,5]
[2]Sakaguchi, Hironobu; Uetake, Yuta; Ohashi, Masato; Niwa, Takashi; Ogoshi, Sensuke; Hosoya, Takamitsu [Journal of the American Chemical Society, 2017, vol. 139, # 36, p. 12855 - 12862]
[3]Jiang, Xinpeng; Wang, Guan; Zheng, Zicong; Yu, Xiaohui; Hong, Ye; Xia, Haoqi; Yu, Chuanming [Organic Letters, 2020, vol. 22, # 24, p. 9762 - 9766]

41
[ 22948-94-3 ]
3,4-diaminobenzamidine monohydrochloride [ No CAS ]
2-(N-acethylindol-3-yl)-3H-benzimidazole-5-N-carboxamidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With p-benzoquinone In ethanol for 4h; Inert atmosphere; Reflux;	General method for preparation of amidino substituted benzimidazoles 3a,b-14a,b General procedure: A mixture of equivalent amounts of corresponding 4-N-substituted-1,2-phenylenediamine 2a-2b, aromatic aldehyde 1a-1l and p-benzoquinone in absolute ethanol (10-15 mL) was stirred at reflux for 4 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature and resulting product was filtered off and washed with diethylether (20 mL). After recrystallization from ethanol/diethylether or ethanol, light powders were obtained.

Reference： [1]Perin, Nataša; Starčević, Kristina; Perić, Mihaela; Paljetak, Hana Čipčić; Matijašić, Mario; Stepanić, Višnja; Verbanac, Donatella; Karminski-Zamola, Grace; Hranjec, Marijana [Croatica Chemica Acta, 2017, vol. 90, # 2, p. 145 - 154]

42
[ 22948-94-3 ]
4-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,2-diamine hydrochloride [ No CAS ]
5-N-(2-imidazolinyl)-2-(N-acethylindol-3-yl)-3H-benzimidazole hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With p-benzoquinone In ethanol for 4h; Inert atmosphere; Reflux;	General method for preparation of amidino substituted benzimidazoles 3a,b-14a,b General procedure: A mixture of equivalent amounts of corresponding 4-N-substituted-1,2-phenylenediamine 2a-2b, aromatic aldehyde 1a-1l and p-benzoquinone in absolute ethanol (10-15 mL) was stirred at reflux for 4 hours under nitrogen atmosphere. The reaction mixture was cooled to room temperature and resulting product was filtered off and washed with diethylether (20 mL). After recrystallization from ethanol/diethylether or ethanol, light powders were obtained.

Reference： [1]Perin, Nataša; Starčević, Kristina; Perić, Mihaela; Paljetak, Hana Čipčić; Matijašić, Mario; Stepanić, Višnja; Verbanac, Donatella; Karminski-Zamola, Grace; Hranjec, Marijana [Croatica Chemica Acta, 2017, vol. 90, # 2, p. 145 - 154]

43
[ 22948-94-3 ]
[ 7303-49-3 ]
[ 1242336-83-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 1-acetyl-3-indolylcarbaldehyde; DL-tryptophan methyl ester In toluene for 2h; Reflux; Stage #2: With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 23h;	Methyl 1-(1-acetyl-1H-indol-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carb -oxylate (3): A stirred solution of DL-tryptophan methyl ester (745 mg, 3.42 mmol) and 1-acetyl-1H-indole-3-carbaldehyde 2 (581 mg, 3.11 mmol) in methylbenzene (40 mL) was heated at reflux for 2 h. After cooling to room temperature, the methylbenzene was removed, replaced with DCM (10 mL), and the reaction mixture cooled to 0 °C. After addition of TFA:DCM (1:2, 12 mL), the reaction mixture was warmed to room temperature and stirred for 23 h. The reaction mixture was diluted with EtOAc (20 mL), H2O (10 mL), and 14% aq NH3 (5 mL) and extracted with EtOAc (5 × 15 mL). The combined organic layers were dried (Na2SO4), concentrated, and the residue purified by flash chromatography (DCM:MeOH = 98:2) to afford tetrahydro-β-carboline 3 (1.035 g, 86% yield) as an inseparable mixture of trans and cis diastereomers. These mixtures could be used directly as the substrates for the next reaction. HRMS (ESI) m/z calcd for C23H21N3O3 [M+H]+ 388.1655, found 388.1653.

Reference： [1]Dai, Jiangkun; Dan, Wenjia; Li, Na; Wang, Junru [European Journal of Medicinal Chemistry, 2018, vol. 157, p. 333 - 338]

44
[ 22948-94-3 ]
[ 107-37-9 ]
(R)-1-[3-(1-hydroxy-but-3-enyl)-indole-1-yl]ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With (S)-3,3’-bis[3,5-bis(trifluoromethyl)phenyl]-1,1’-biisoquinoline N,N’-dioxide; N-ethyl-N,N-diisopropylamine In tetrahydrofuran; acetonitrile at -50 - -40℃; for 71h; Inert atmosphere; enantioselective reaction;

Reference： [1]Reep, Carlyn; Morgante, Pierpaolo; Peverati, Roberto; Takenaka, Norito [Organic Letters, 2018, vol. 20, # 18, p. 5757 - 5761]

45
[ 22948-94-3 ]
[ 104-03-0 ]
3-(4-nitrophenylethenyl-E)-N-acetylindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; pyridine at 100℃; for 6h; Reflux;	Synthesis of substituted ethenyl indoles General procedure: The substituted ethenyl indoles were synthesized by the condensation of p-substituted phenyl acetic acid with the corresponding 3-formylindole or its derivatives in presence of pyridine-pipridine mixture. For this purpose, 3-formylindole was taken in freshly distilled pyridine (10 mL), pipiridine (0.6 mL) and p-nitrophenyl acetic acid (2 molar equivalent with respect to 3-formylindole) in a round bottom flask fitted with a reflux condenser. The reaction mixture was heated at 100°C for 6 h. The reaction mixture was cooled to RT and treated with 100 mL of diluted hydrochloric acid to remove excess of pyridine from the reaction mixture. The product was extracted with diethyl ether and purified by column chromatography using 2-10% ethyl acetate in petroleum ether as the eluting solvent.

Reference： [1]Kumar, Jagdeep; Kumar, Naresh; Hota, Prasanta Kumar [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2018, p. 301 - 307]

46
[ 22948-94-3 ]
[ 590-93-2 ]
[ 7188-38-7 ]
[ 95-55-6 ]
N-(1-(1-acetyl-1H-indol-3-yl)-2-(tert-butylamino)-2-oxoethyl)-N-(2-hydroxyphenyl)but-2-ynamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With sodium sulfate In methanol at 20℃;

Reference： [1]He, Yi; Liu, Zhen; Wu, Danjun; Li, Zhenghua; Robeyns, Koen; Van Meervelt, Luc; Van Der Eycken, Erik V. [Organic Letters, 2019, vol. 21, # 12, p. 4469 - 4474]

47
[ 626-35-7 ]
[ 22948-94-3 ]
(Z)-ethyl 3-(1-acetyl-1H-indol-3-yl)-2-nitroprop-2-enoate [ No CAS ]
[ 16814-99-6 ]

Yield	Reaction Conditions	Operation in experiment
53.488 % de	With acetic acid; 3-amino propanoic acid In benzene for 5h; Reflux; Dean-Stark; Overall yield = 55 %;	Ethyl 3-(1-benzyl-1H-indol-3-yl)-2-nitroprop-2-enoate (6) General procedure: A mixture of 0.67 g (5 mmol) of ethyl nitroacetate, 1.17 g (5 mmol) of 1-benzyl-1H-indole-3-carbaldehyde (3), 0.19 g of β-alanine, and 0.8 mL of glacial acetic acid in 20 mL of anhydrous benzene was refluxed for 5 h in a flask equipped with a Dean-Stark trap. After cooling, the mixture was washed with brine, the organic phase was dried over calcined MgSO4, the solvent was removed, and the residue was subjected to chromatography on silica gel.

Reference： [1]Baichurin; Fedorushchenko; Aboskalova; Baichurina; Felgendler; Makarenko [Russian Journal of General Chemistry, 2019, vol. 89, # 5, p. 870 - 880][Zh. Obshch. Khim., 2019, vol. 89, # 5, p. 671 - 683,7]

48
[ 22948-94-3 ]
[ 614-21-1 ]
3-(1-acetyl-1H-indol-3-yl)-2-nitro-1-phenylprop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With acetic acid; 3-amino propanoic acid In benzene at 20℃; for 2h; Reflux; Dean-Stark;	3-(1-Benzyl-1H-indol-3-yl)-2-nitro-1-phenylprop-2-en-1-one (15) General procedure: b. A mixture of 0.82 g (5 mmol) of nitroacetophenone,1.17 g (5 mmol) of aldehyde 3, 0.19 g of β-alanine, and 4 mL of glacial acetic acid in 40 mL of anhydrous benzene was refluxed for 4 h in a flask equipped with a Dean-Stark trap. After cooling, the mixture was washed with water and dried over calcined MgSO4, the solvent was removed, and the precipitate was filtered off and dried.

Reference： [1]Baichurin; Fedorushchenko; Aboskalova; Baichurina; Felgendler; Makarenko [Russian Journal of General Chemistry, 2019, vol. 89, # 5, p. 870 - 880][Zh. Obshch. Khim., 2019, vol. 89, # 5, p. 671 - 683,7]

49
[ 13218-13-8 ]
[ 22948-94-3 ]
3-(1-acetyl-1H-indol-3-yl)-2-nitroprop-2-enenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol at 20℃; for 24h;	3-(1H-Indol-3-yl)-2-nitroprop-2-enenitrile (18) General procedure: A suspension of 1.45 g (10 mmol) of aldehyde 1 in 15 mL of anhydrous ethanol was added to 0.86 g (10 mmol) of crude nitroacetonitrile. The mixture turned dark, and an orange crystalline solid separated on slight heating. The mixture was left to stand for 24 h at room temperature, and the precipitate was filtered off and dried.

Reference： [1]Baichurin; Fedorushchenko; Aboskalova; Baichurina; Felgendler; Makarenko [Russian Journal of General Chemistry, 2019, vol. 89, # 5, p. 870 - 880][Zh. Obshch. Khim., 2019, vol. 89, # 5, p. 671 - 683,7]

50
[ 22948-94-3 ]
[ 137-07-5 ]
1-(3-(benzo[d]thiazol-2-yl)-1H-indol-1-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With TPGS-750-M In water at 20℃; for 12h; Sealed tube;	Representative experimental procedure for the synthesis 2-indolylbenzothiazole General procedure: To dried seal tube equipped with a stir bar, 2-aminothiophenol 1a (25 mg, 0.2 mmol), indole-3-carboxaldehyde 2a (34.8 mg, 0.24 mmol, 1.2 equiv), and 1 mL of aqueous TPGS-750-M (2% w/w) were added. The resultant mixture was stirred at room temperature for 12 h followed by aqueous workup using EtOAc as organic solvent. The collected organic layers were dried overanhydrous Na2SO4 and concentrated under reduced pressure. The crude products were adsorbed on silica gel and purified by column chromatography (eluent- Hexane:EtOAc) to getthe analytically pure compound 3a as white crystalline powder (35 mg, 88%);

Reference： [1]Kumar, Sanjeev; Parshuram Satpute, Dinesh; Nikhil Vaidya, Gargi; Nagpure, Mithilesh; Kumar Lokhande, Shyam; Meena, Deepak; Kumar, Dinesh [Tetrahedron Letters, 2020, vol. 61, # 25]

51
[ 22948-94-3 ]
C₁₁H₈INO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With N-iodo-succinimide; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 20℃; for 4h; Green chemistry;	7 Example 7 Add 0.5 mmol N-acetylindole-3-carbaldehyde 1g and 0.5 mmol N-iodosuccinimide 2a to a 10 mL single-neck flask, add the solvent 1,2-dichloroethane (3 mL), and stir. 1 mmol p-toluenesulfonic acid (TsOH) was added dropwise, and reacted at room temperature for 4 h. After the completion of the reaction, extraction was performed, the reaction solution was rotary evaporated under reduced pressure to remove the solvent, and the residue was purified by a fast silica gel column to obtain 3 g of the corresponding 5-iodoindole compound with a yield of 70%.

Reference： [1]Current Patent Assignee: NORTHWESTERN UNIVERSITY (ILLINOIS) - CN112479972, 2021, A Location in patent: Paragraph 0026-0027

52
[ 576-15-8 ]
[ 75-50-3 ]
[ 22948-94-3 ]

Yield	Reaction Conditions	Operation in experiment
65%	With tetrabutyl ammonium fluoride; water at 80℃; for 25h; Electrolysis; Inert atmosphere; Green chemistry;

Reference： [1]Cheng, Didi; Li, Jingyi; Li, Yujin; Ling, Fei; Liu, Lei; Liu, Tao; Zhong, Weihui [Green Chemistry, 2021, vol. 23, # 11, p. 4107 - 4113]

53
[ 22948-94-3 ]
1-acetyl-4-chloro-1H-indole-3-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-chloro-succinimide; palladium diacetate; trifluoroacetic acid; 4-Nitroanthranilic acid In chlorobenzene at 50℃; for 24h; Sealed tube;

Reference： [1]Kuang, Guanghua; Liu, Dandan; Chen, Xuerong; Liu, Guangyuan; Fu, Yang; Peng, Yiyuan; Li, Hua; Zhou, Yirong [Organic Letters, 2021, vol. 23, # 21, p. 8402 - 8406]

54
[ 22948-94-3 ]
1,4-diacetyl-3-[(tert-butyldimethylsilyl)oxy]methyl}piperazine-2,5-dione [ No CAS ]
(Z)-1-acetyl-3-{(1-acetyl-1H-indol-3-yl)methylene}-6-[(tert-butyldimethylsilyl)oxy]methyl}piperazine-2,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 1-acetyl-3-indolylcarbaldehyde; 1,4-diacetyl-3-[(tert-butyldimethylsilyl)oxy]methyl}piperazine-2,5-dione In N,N-dimethyl-formamide at 0℃; for 0.25h; Inert atmosphere; Stage #2: With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃; for 15h; Inert atmosphere;

Reference： [1]Nishiuchi, Kota; Ohashi, Hirofumi; Nishioka, Kazane; Yamasaki, Masako; Furuta, Masateru; Mashiko, Takumi; Tomoshige, Shusuke; Ohgane, Kenji; Kamisuki, Shinji; Watashi, Koichi; Kuramochi, Kouji [Journal of Natural Products, 2022, vol. 85, # 1, p. 284 - 291]

55
[ 22948-94-3 ]
1,4-diacetyl-3-[(tert-butyldimethylsilyl)oxy]methyl}piperazine-2,5-dione [ No CAS ]
C₂₄H₃₁N₃O₅Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium-t-butoxide In N,N-dimethyl-formamide at 0 - 20℃;	1 Synthesis Example 1: Compound 1 General procedure: According to the above general synthesis method 1, aldehyde A1 (37.4 mg, 0.20 mmol) having the chemical structure shown below and diketopiperazine B (137 mg, 0.40 mmol) are dissolved in DMF (2.0 mL) and potassium tert-butoxide (65.3 mg, 0.58 mmol) was added and reacted to give compound C1 (83.5 mg, 89%) as a yellow solid.

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF TOKYO - WO2022/113987, 2022, A1 Location in patent: Paragraph 0052-0053; 0057-0061

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	22948-94-3	MDL No. :	MFCD00039691
Formula :	C₁₁H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LCJLFGSKHBDOAY-UHFFFAOYSA-N
M.W :	187.19	Pubchem ID :	89915
Synonyms :

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

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
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P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
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P406	Store in corrosive resistant/ container with a resistant inner liner.
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P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H241	Heating may cause a fire or explosion
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H250	Catches fire spontaneously if exposed to air
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H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 22948-94-3 ] {[proInfo.proName]}

Quality Control of [ 22948-94-3 ]

Related Doc. of [ 22948-94-3 ]

Product Details of [ 22948-94-3 ]

Safety of [ 22948-94-3 ]

Application In Synthesis of [ 22948-94-3 ]

[ 22948-94-3 ] Synthesis Path-Upstream 1~2

[ 22948-94-3 ] Synthesis Path-Downstream 1~55

Related Functional Groups of
[ 22948-94-3 ]

Aldehydes

Amides

Related Parent Nucleus of
[ 22948-94-3 ]

Indoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 22948-94-3 ] {[proInfo.proName]}

Quality Control of [ 22948-94-3 ]

Related Doc. of [ 22948-94-3 ]

Product Details of [ 22948-94-3 ]

Safety of [ 22948-94-3 ]

Application In Synthesis of [ 22948-94-3 ]

[ 22948-94-3 ] Synthesis Path-Upstream 1~2

[ 22948-94-3 ] Synthesis Path-Downstream 1~55

Related Functional Groups of [ 22948-94-3 ]

Aldehydes

Amides

Related Parent Nucleus of [ 22948-94-3 ]

Indoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 22948-94-3 ]

Related Parent Nucleus of
[ 22948-94-3 ]