Category: 10601-19-1

Gao, Qinghe et al. published their research in Organic & Biomolecular Chemistry in 2018 | CAS: 10601-19-1

5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C10H9NO2

I2-Triggered N-O cleavage of ketoxime acetates for the synthesis of 3-(4-pyridyl)indoles was written by Gao, Qinghe;Wang, Yakun;Wang, Qianqian;Zhu, Yanping;Liu, Zhaomin;Zhang, Jixia. And the article was included in Organic & Biomolecular Chemistry in 2018.Computed Properties of C10H9NO2 This article mentions the following:

Synthesis of 3-(4-pyridyl)indole derivatives I (R = H, 5-OCH2C6H5, 6-F, 7-NO2, etc.; R1 = H, CH3; Ar = C6H5, 2H-1,3-benzodioxol-5-yl, naphthalen-2-yl, etc.) and II from a facile and complementary [3+2+1] annulation of aryl ketoxime acetates Ar(CH3)C=NOC(O)CH3 and 1,2,3,4-tetrahydronaphthalen-1-ylideneamino acetate and 3-formylindoles III is reported. The condensation reaction demonstrated that I2 was capable of triggering N-O bond cleavage of ketoxime acetates to generate iminyl radicals via a single electron transfer pathway. This direct and operationally simple protocol provides a fundamental platform to synthesize 3-(4-pyridyl)indole derivatives I and II with high functional group compatibility and high regioselectivity. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1Computed Properties of C10H9NO2).

5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1) belongs to indole derivatives. Indole produced by Proteus, Pseudomonas, Escherichia and other species was shown to be a growth promoting factor in Arabidopsis thaliana. Due to this activity, the indole ring system has become an important component or intermediate in the synthesis of heterocycles.Computed Properties of C10H9NO2

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Lan, Linfeng et al. published their research in Advanced Materials (Weinheim, Germany) in 2022 | CAS: 10601-19-1

5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Name: 5-Methoxy-1H-indole-3-carbaldehyde

Organic Single-Crystal Actuators and Waveguides that Operate at Low Temperatures was written by Lan, Linfeng;Li, Liang;Di, Qi;Yang, Xuesong;Liu, Xiaokong;Naumov, Pance;Zhang, Hongyu. And the article was included in Advanced Materials (Weinheim, Germany) in 2022.Name: 5-Methoxy-1H-indole-3-carbaldehyde This article mentions the following:

Applications in extreme conditions, such as those encountered in space exploration, require lightweight materials that can retain their elasticity in extremely cold environments. However, cryogenic treatment of most soft polymeric and elastomeric materials results in complete loss of their ability for elastic flow, whereby such materials that are normally ductile become stiff, brittle, and prone to cracking. Here, a facile method for preparation of hybrid organic crystalline materials that are not only cryogenically robust but are also capable of large, recoverable, and reversible deformation at low temperatures is reported. To that end, flexible organic crystals are first mech. reinforced by a polymer coating and combined with a thermally responsive polymer. The resulting hybrid materials respond linearly and reversibly to temperatures from -15 to -120掳 C without fatigue in air as well as in cold vacuum. The approach proposed here not only circumvents one of the main drawbacks that are inherent to the amorphous nature and has thus far limited the applications of polymeric materials at low temperatures, but it also provides a cost-effective access to a myriad of lightweight sensing, electronic, optical or actuating devices that can operate in low-temperature environmental settings. In the experiment, the researchers used many compounds, for example, 5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1Name: 5-Methoxy-1H-indole-3-carbaldehyde).

5-Methoxy-1H-indole-3-carbaldehyde (cas: 10601-19-1) belongs to indole derivatives. Indole, first isolated in 1866, and it is commonly synthesized from phenylhydrazine and pyruvic acid, although several other procedures have been discovered. They are capable of binding to a variety of receptors with high affinity and thus have applications in a wide range of therapeutic areas.Name: 5-Methoxy-1H-indole-3-carbaldehyde

Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Some tips on 10601-19-1

The synthetic route of 10601-19-1 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10601-19-1,5-Methoxy-1H-indole-3-carbaldehyde,as a common compound, the synthetic route is as follows.

a. 5-Methoxy-1-methylindole-3-carboxaldehyde (43) 5-Methoxyindole-3-carboxaldehyde (300 mg, 1.71 mmol) was added in portions over 5 min to a suspension of sodium hydride (82 mg, 2.05 mmol, 60% dispersion in mineral oil) in DMF (8 mL) stirring under argon. The mixture was stirred for 30 min, methyl iodide (0.13 mL, 2.05 mmol) was added and the mixture was stirred for 1 h. Sodium bicarbonate (10%, 40 mL) was added and the mixture was extracted with EtOAc (4*). The combined organic layers were washed with sodium bicarbonate (10%, 2*) and saturated NaCl, dried (MgSO4), filtered and evaporated. Column chromatography of the crude product (50:50 EtOAc:hexanes) afforded 43 (320 mg, 99%) as a light yellow solid; Rf=0.35 (50:50 EtOAc:hexanes); mp=130-132 C.; lit mp=132-133 C.53; 1H NMR (CDCl3): delta 9.95 (s, 1H), 7.79 (d, 1H, J=2.4 Hz), 7.62 (s, 1H), 7.25 (d, J=8.8 Hz), 6.96 (dd, 1H, J=2.4 and 8.9 Hz), 3.90 (s, 3H), 3.85 (s, 3H)., 10601-19-1

The synthetic route of 10601-19-1 has been constantly updated, and we look forward to future research findings.

Reference：
Patent; Borch, Richard F.; Hernick, Marcy; Flader, Carolee; US2003/8850; (2003); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Analyzing the synthesis route of 10601-19-1

As the paragraph descriping shows that 10601-19-1 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10601-19-1,5-Methoxy-1H-indole-3-carbaldehyde,as a common compound, the synthetic route is as follows.

General procedure: Compounds 7-9 were synthesized from the corresponding compounds 4-6. A solution of compounds 4-6 (60 mmol) in THF (30 mL) were added dropwise to a suspension of NaH (3.60 g, 60% dispersion in mineral oil, 150 mmol) in THF (30 mL) at 0 C. After stirring for 15 min, the heterogeneous mixture was treated with iodomethane (5.04 mL, 79.2 mmol) at room temperature for 1 h. Then the reaction mixture was cooled to 0 C, quenched with saturated NH4Cl (60 mL), and extracted with ether (3 * 50 mL). The organic layers were combined, washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to give 1-Methyl-1H-indole-3-carboxaldehyde (7-9), a light brown solid. The crude 7-9 were used in the next step without any further purification., 10601-19-1

As the paragraph descriping shows that 10601-19-1 is playing an increasingly important role.

Reference：
Article; Wang, Yan-Ting; Qin, Ya-Juan; Yang, Na; Zhang, Ya-Liang; Liu, Chang-Hong; Zhu, Hai-Liang; European Journal of Medicinal Chemistry; vol. 99; (2015); p. 125 – 137;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Downstream synthetic route of 10601-19-1

10601-19-1 5-Methoxy-1H-indole-3-carbaldehyde 82758, aindole-building-block compound, is more and more widely used in various fields.

10601-19-1, 5-Methoxy-1H-indole-3-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A solution of 5-methoxyindole-3-carboxaldehyde (80 g) in dimethylformamide (1 L) under nitrogen was treated portion-wise with sodium hydride (20.1 g, 60% dispersion in mineral oil) over 15 minutes. After stirring at ambient temperature for 30 minutes the mixture was treated dropwise with methyl iodide (31.3 mL) over 10 minutes and stirring was then continued for a further 2 hours. The reaction mixture was poured cautiously into water then extracted with ethyl acetate. The organic phase was washed with water, then dried over sodium sulfate and then evaporated. The residue was triturated with pentane to give the title compound (76 g) as a pale brown solid, m.p. 133-134 C. 1H NMR [(CD3)2SO]: delta 9.86 (1H, s); 8.20 (1H, s); 7.60 (1H, d, J=2.6 Hz); 7.50 (1H, d, J=8.9 Hz); 6.96 (1H, dd, J=8.9 and 2.6 Hz); 3.86 and 3.80 (6H, s)., 10601-19-1

10601-19-1 5-Methoxy-1H-indole-3-carbaldehyde 82758, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; Cox, Paul J.; Majid, Tahir N.; Lai, Justine Y.Q.; Morley, Andrew D.; Amendola, Shelley; Deprets, Stephanie D.; Edlin, Christopher; US2004/9983; (2004); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Simple exploration of 10601-19-1

10601-19-1, The synthetic route of 10601-19-1 has been constantly updated, and we look forward to future research findings.

10601-19-1, 5-Methoxy-1H-indole-3-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5-methoxy-indole 22 (1.78 g, 9.40 mmol) was added gradually and under dry argon to a suspension of NaH (0.564 g of a 60% dispersion, 14.11 mmol) in dry DMF (4 mL). The suspension was stirred at room temperature for 10 min and cooled to 0 C, and MeI (0.81 g, 5.71 mmol) was added over 5 min. The solution was then heated at 40 C for 30 min, cooled, poured into cold water. The mixture was extracted with EtOAc (2× 150 mL), dried and evaporated. The residue was used without purification (1.03 g, 95%). 1H NMR (300 MHz, DMSO-d6): delta (ppm) 9.72 (s, 1H), 8.45 (s, 1H), 7.82 (d, J = 9.1 Hz, 1H), 7.37 (d, J = 9.1 Hz, 1H), 3.93 (s, 3H), 3.91 (s, 3H); MS (ESI) m/z: 190.1 [M+H]+.

10601-19-1, The synthetic route of 10601-19-1 has been constantly updated, and we look forward to future research findings.

Reference：
Article; Xu, Shengtao; Yao, Hong; Pei, Lingling; Hu, Mei; Li, Dahong; Qiu, Yangyi; Wang, Guangyu; Wu, Liang; Yao, Hequan; Zhu, Zheying; Xu, Jinyi; European Journal of Medicinal Chemistry; vol. 132; (2017); p. 310 – 321;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Brief introduction of 10601-19-1

As the paragraph descriping shows that 10601-19-1 is playing an increasingly important role.

10601-19-1, 5-Methoxy-1H-indole-3-carbaldehyde is a indole-building-block compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: The relevant indole-3-carboxaldehyde (2a-c, 10 mmol) in THF(25 mL) was added dropwise to a stirred solution of NaH (25 mmol)in THF (25 mL) at 0 C and CH3I (13.2 mmol) was added after 15 minstirring. The reaction mixturewas moved to room temperature andstirred for further 24 h. Then the solvent was removed in vacuumand the residue was extracted by ethyl acetate. The organic layerwas washed with brine, dried over anhydrous sodium sulfate,filtered and concentrated in vacuum. Recrystallization affordedcompound 3a-c with yields of 93.4-97.5%., 10601-19-1

As the paragraph descriping shows that 10601-19-1 is playing an increasingly important role.

Reference：
Article; Chen, Kun; Zhang, Ya-Liang; Fan, Jing; Ma, Xiang; Qin, Ya-Juan; Zhu, Hai-Liang; European Journal of Medicinal Chemistry; vol. 156; (2018); p. 722 – 737;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

New learning discoveries about 10601-19-1

10601-19-1 5-Methoxy-1H-indole-3-carbaldehyde 82758, aindole-building-block compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10601-19-1,5-Methoxy-1H-indole-3-carbaldehyde,as a common compound, the synthetic route is as follows.

To a suspension of NaH (8.9 g, 0.223 mol) in DMF (300 mL) was cooled in an ice-bath. To this, a solution of the starting amine (30 g, 0.171 mol) in DMF (150 mL) was added dropwise. The reaction mixture was stirred at rt for 60 minutes. Then iodomethane (31.5 g, 0.223 mol) was added. The reaction mixture was stirred at rt for 1 hour. Then the mixture was poured onto 10% aqueous solution of NaHCO3, extracted with EA. The combined organicphases were washed with 10% aqueous solution of NaHCO3, brine and dried. The solution was concentrated to get crude product, which was triturated from EAHex to afford product as a light-yellow solid (29.5 g, 91.2%), 10601-19-1

10601-19-1 5-Methoxy-1H-indole-3-carbaldehyde 82758, aindole-building-block compound, is more and more widely used in various fields.

Reference：
Patent; GENENTECH, INC.; DRAGOVICH, Peter; PEI, Zhonghua; PILLOW, Thomas; SADOWSKY, Jack; VERMA, Vishal; ZHANG, Donglu; (268 pag.)WO2018/31662; (2018); A1;,
Indole alkaloid derivatives as building blocks of natural products from?Bacillus thuringiensis?and?Bacillus velezensis?and their antibacterial and antifungal activity study
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles