Month: August 2021

Application of 169037-23-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

The synthetic route of 5-(Trifluoromethoxy)indoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C16H13FN2O3

EXAMPLE 3: Preparation of 7V-(3-(hvdroxycarbamoyl)propyl)5-(TZ)- (5- fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-lH-pyrrole- 3-carboxamide (compound 3) Step 3a. Methyl 4-(5-((Z)-(5-fluoro-2-oxoindolin-3-ylidene)methyl) -2,4- dimethyl- lH-pyrrole-3-carboxamido)butanoate (Compound 110-3) To a stirred solution of compound 1 (0.5 g, 1.67 mmol) in DMF (35 mL) at room temperature was added etaOBt (1.02 g, 7.52 mmol), triethylamine(2.12 mL, 15.03 mmol), ECDI-HCl(1.44 g, 1.52 mmol) and methyl 4-aminobutanate hydrochloride(0.77 g, 5.0 mmol) successively. The mixture was stirred for 24 h at room temperature and then was diluted with water (20 mL), brine (20 mL) and saturated bicarbonate solution (20 mL) and the pH of solution was adjusted to 11-12 with 10 mol/L NaOH. The mixture was filtrated, the solid was collected, washed with water and dried to obtain crude yellow solid product 110-3 (0.32 g, 48.3%). LCMS: m/z 400(M+l), 1H NMR(DMSO-^6) deltal.77 (m, 2H), 2.39 (m, 4H), 2.42 (s, 3H), 2.49 (s, 3H), 3.23 ( t, 2H), 6.85 (m, 2H), 7.60 (t, IH), 7.67 (s, IH), 7.71 (m, IH), 10.89 (s, IH), 13.68 (s, IH).

According to the analysis of related databases, 356068-93-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CURIS, INC.; WO2008/33743; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1035235-27-8, A common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Step a. To a stirred solution of tert-butyl 4-bromoisoindoline-2-carboxylate (Intermediate 1, 0.35 g, 1.185 mmol) in 1,4-dioxane: water (4: 1; 20 ml) was added Cs2C03 (0.77 g, 2.371 mmol) at rt under nitrogen. The reaction was purged with nitrogen for 15 min. Pd(PPh3)4 (0.14 g, 0.118 mmol) was added to the reaction mixture and purged with nitrogen for 10 min. 3- (Methoxycarbonyl)phenylboronic acid (CAS Number 99769-19-4; available from Combi Blocks) (0.26 g, 1.422 mmol) was added to the reaction mixture. The reaction mixture was heated at 80C for 24 h. The resulting reaction mixture was cooled to rt, poured into water (20 ml) and extracted with EtOAc (3 x 50). The combined organic phase was washed with brine (80 ml). The organic phase was separated, dried over Na2S04, filtered and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography (5% EtOAc in hexane) yielding tert-butyl 4-(3- (methoxycarbonyl)phenyl)isoindoline-2-carboxylate (0.33 g, 0.932 mmol). LCMS: Method A, 2.782 min, MS: ES+ 298.4 (M-56); 1H NMR (400 MHz, CDC13) delta ppm 8.04 – 8.11 (m, 2 H), 7.62 (d, J=7.2 Hz, 1H), 7.49 – 7.58 (m, 2 H), 7.40 (t, J=7.2 Hz, 1H), 7.31 – 7.33 (m, 1H), 4.69 – 4.79 (m, 4 H), 3.95 (s, 3 H), 1.53 (s, 9 H).

The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H4F3NO3

General procedure: To the reaction mixture containing isatin (0.5mmol) in water (2mL), indole (0.5mmol), diethanolamine (20mol %) was slowly added at room temperature. After thecompletion of reaction as monitored by TLC, the reaction mixture was washed with brine solution and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the product was purified by flash chromatography on the silica gel column using a gradient of petroleum ether/ethyl acetate, as eluent to afford pure products 1-41.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Sai Prathima, Parvathaneni; Rajesh, Pamanji; Venkateswara Rao, Janapala; Sai Kailash, Uppalapati; Sridhar, Balasubramanian; Mohan Rao, Mandapati; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 155 – 159;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 20780-72-7, name is 4-Bromoisatin, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 20780-72-7, Quality Control of 4-Bromoisatin

General procedure: To a solution of isatin 1 (1 mmol) in toluene (5 mL) was added the solution of trialkyl/aryl Al 2 (2 mmol, 2 M in toluene) dropwise at RT. Then the mixture was heated at 70 °C and stirred for additional 3?3.5 h (see Table 2). The reaction was monitored by TLC. After completion of the reaction, toluene was evaporated and extracted with ethyl acetate (3 × 5 mL). The combined organic layer was washed with brine solution, dried over anhydrous Na2SO4, and concentrated under reduced pressure (rotary evaporator). The crude products were purified by silica gel column chromatography using ethyl acetate/hexanes (4:1?1:1). All compounds were characterized by (MP, NMR, Mass, and IR) spectral data.18

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromoisatin, and friends who are interested can also refer to it.

Reference:
Article; Kumar, G. Santosh; Ramesh, Palakuri; Kumar, A. Sanjeeva; Swetha; Meshram; Tetrahedron Letters; vol. 54; 37; (2013); p. 5048 – 5051;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1074-82-4, The chemical industry reduces the impact on the environment during synthesis 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, I believe this compound will play a more active role in future production and life.

[0714] Step 11: Synthesis of 2-(5-bromopentyl) isoindoline-1,3-dione (14-k) To a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 min at room temperature. After complete addition, the reaction mixture was stirred at 90C for 18 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65% yield). 1H NMR (400 MHz, CDCl3): delta 7.82 (dd, J = 5.5, 3.1Hz, 2H), 7.69 (dd, J = 5.5, 3.0 Hz, 2H), 3.68 (t, J = 7.2 Hz, 2H), 3.38 (t, J = 6.8 Hz, 2H), 1.93-1.85 (m, 2H), 1.70 (p, J = 7.5 Hz, 2H), 1.53-1.43 (m, 2H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Potassium 1,3-dioxoisoindolin-2-ide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; LADNER, Robert D.; (345 pag.)WO2018/128720; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromoisatin

Into a 250-mL round-bottom flask, was placed 4-bromo-2,3-dihydro-1H-indole-2,3- dione (2.25 g, 9.95 mmol, 1.00 equiv), N,N-dimethylformamide (50 mL), sodium hydride (480 mg, 12.00 mmol, 2.00 equiv), and iodomethane (1.7 g, 11.98 mmol, 1.20 equiv). The resulting solution was stirred for 1 h at room temperature in a water/ice bath. The resulting solution was diluted with 800 mL of EA then washed with 4×50 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 2 g (84percent) of 4-bromo-1-methyl-2,3-dihydro-1H-indole-2,3-dione as a red solid

According to the analysis of related databases, 20780-72-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LYCERA CORPORATION; AICHER, Thomas, Daniel; PADILLA, Fernando; TOOGOOD, Peter, L.; CHEN, Shoujun; (331 pag.)WO2016/138335; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 16800-68-3,Some common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: A 10 mL glass tube equipped with a stirring bar was charged with the isatin-derived N-Boc ketimine 1 (0.44 mmol, 1.2 equiv), the N-acetylindolin-3-one 2 (0.4 mmol, 1.0 equiv), catalyst 4o (0.02 mmol, 2 mol%) and CH2Cl2 (4.0 mL). The resulting solution was stirred at r.t. for the indicated time. The solvent was then evaporated to give the crude product, which was directly purified by flash chromatography (n-pentane/EtOAc, 4:1 to 1:1) to provide the desired products 3a-t.

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gajulapalli, V. Pratap Reddy; Jafari, Ehsan; Kundu, Dipti S.; Mahajan, Suruchi; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter; Synthesis; vol. 49; 22; (2017); p. 4986 – 4995;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 446292-08-6, These common heterocyclic compound, 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

9 g (0.021 mol) of 2-({(5S)-2-Oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-1 ,3-oxazolidin-5- yl}methyl)-1 H-isoindole-1 ,3(2H)-dione (II), 8.06 mL of methylamineamine (40% aqueous solution, 0.235 mol) and 80 mL of ethanol were charged in a 100 mL flask and the reaction mixture was heated to 65 C for 2h. Then, 10 mL of a 20% HCI solution was added until the pH of the reaction mass was adjusted to 2.7. The reaction mass was cooled to 30 C and the resulting solid was filtered off, washed with ethanol and dried under vacuum at 60 C.Yield: 5.3 g. Molar yield: 75.7%. HPLC purity: 93.9%

The synthetic route of 446292-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LABORATORIOS LESVI, S. L.; VISHNU NEWADKAR, Ravindranath; CHANGDEO GAIKWAD, Avinash; MADHUKAR HARAD, Ajay; DALMASES BARJOAN, Pere; WO2013/53739; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 7477-63-6, Computed Properties of C8H4ClNO2

General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken ina 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, thereaction mixture was allowed to cool, quenched with water (10 mL) and extractedwith DCM (3 x 20 mL). The combined organic extracts were dried over anhydrousNa2SO4, filtered and volatiles were removed in vacuo. Thecrude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 percent ethyl acetate in petroleum ether to afford compound (4).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Karmakar, Rajiv; Kayal, Utpal; Bhattacharya, Biswajit; Maiti, Gourhari; Tetrahedron Letters; vol. 55; 7; (2014); p. 1370 – 1372;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem