Category: indolines-derivatives

Electric Literature of 35197-64-9, 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. 35197-64-9, name is 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid, This compound has unique chemical properties. The synthetic route is as follows.

3-(3-chlorophenyl)-2-mercapto-8-methylquinazolin-4(3H)-one (1-3) was prepared as described before . 3-(3-chlorophenyl)-2-mercapto-8-methylquinazolin-4(3H)-one (1-3,211 mg, 0.70 mmol, 1.0 equiv), 2-bromo-4-(l ,3-dioxo-l,3-dihydro-2H-isoindol-2-yl)butanoic acid (3-4, 284 mg, 0.91 ramol, 1.3 equiv.), and triethyl amine (588 muL, 4.2 mmol, 6 equiv.) were dissolved in anhydrous DMF (1 mL) and stirred at 75 0C. When LCMS indicated the reaction was complete, the crude reaction mixture was partitioned between ethyl acetate and 0.1 M HCl, the aqueous phase drained and the organic layer washed twice more with 0.1 M HCl followed by brine to yield the product (3-5). LRMS m/z (M+H) 533.8 found, 533.1 required.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK & CO., INC.; WO2009/102537; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 341988-36-1, name is Methyl indoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 341988-36-1

Example 1: Synthesis and analytical data of l-(4-Ethoxy-benzenesulfonyl)-2,3-dihydro- indole-6-carboxylic acid methyl esterl-(4-Ethoxy-benzenesulfonyl)-2,3-dihydro-indole-6-carboxylic acid methyl ester was synthesized starting from commercial available indoline-6-carboxylic acid methylester following the general procedure A using commercial available 4-ethoxy-benzene sulfonylchloride. ESI+, m/z+l=362, found; IH-NMR (CDCl3): delta(ppm)=8.25 (s, IH), 7.8.-7.65 (m, 3H), 7.15 (d, J=2Hz; 1H); 6.90 (d; J=3Hz; 2H), 4,10-3=90 (m, 7H), 2,95 (t, J=2Hz, 2H), 1.40 (t, J=2Hz, 3H) General procedure A: Coupling of sulfonic acid chlorides to indolines0.5 mmol of the Indoline were dissolved in a mixture of 2.5 mL dry dichloromethane and 0.5 mL dry pyridine under a nitrogen atmosphere. 0.6 mmol of the sulfonic acid chloride were added. The mixture was stirred at room temperature in a sealed tube for 6.5 h. Thereafter solvent was evaporated under vacuum. The crude product was purified by preparative HPLC-MS to give the corresponding sulfonamide.

The synthetic route of 341988-36-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EUROPEAN MOLECULAR BIOLOGY LABORATORY; ELARA PHARMACEUTICALS GMBH; JANSSEN, Bernd; AMMENN, Jochen; MUeLBAIER, Marcel; ALONSO, Jorge; WO2010/17827; (2010); 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., category: indolines-derivatives

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 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; 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

Adding a certain compound to certain chemical reactions, such as: 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, 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 60434-13-1, COA of Formula: C9H6ClNO2

General procedure: A solution of N-methylisatin (322 mg, 2.0 mmol), phenylacetylene (306 mg, 3.0 mmol), CuI (76 mg, 0.4 mmol), and Cs2CO3 (978 mg, 3.0 mmol) in CH3CN (4.0 mL) was stirred at room temperature for 18 h. After aqueous extractive workup and column chromatographic purification process (CH2Cl2/EtOAc, 15:1) 1a was obtained as a pale yellow solid, 347 mg (66%).1-12 Other compounds were prepared similarly,1-12 and the propargylic alcohols were used in the next hydrogenation step without further identification process.

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:
Note; Seo, Da Young; Min, Beom Kyu; Roh, Hwa Jung; Kim, Jae Nyoung; Bulletin of the Korean Chemical Society; vol. 38; 10; (2017); p. 1231 – 1234;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 102359-00-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 102359-00-2 name is 2-Oxoindoline-5-carboxylic Acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: Compound 7 (2.1 g, 0.012 mol) and HBTU (5.0 g, 0.013 mol) were dissolved in dry DMF, in a 250 ml round bottom flask. DIPEA (6.5 ml, 0.037 mol) was added and the reaction mixtures were stirred for 30 min. L or D- phenylalanine methyl ester hydrochloride (3.0 g, 0.014 mol) or glutamic acid dimethyl ester hydrochloride (3.0 g 0.014 mol) was added and the reaction mixture was kept stirring overnight under ambient conditions. Reaction monitoring by TLC was performed on silica gel plates using CHCl3:MeOH 9:1 as eluent. Saturated NaHCO3 solution (150 ml) was added to the mixture and the precipitate was filtered, washed with saturated NaHCO3 solution and water. The crude product was purified by column chromatography CHCl3:MeOH (95:5) to give the product as white to off-white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Oxoindoline-5-carboxylic Acid, and friends who are interested can also refer to it.

Reference:
Article; Nemes, Zoltan; Takacs-Novak, Krisztina; Voelgyi, Gergely; Valko, Klara; Beni, Szabolcs; Horvath, Zoltan; Szokol, Balint; Breza, Nora; Dobos, Judit; Szantai-Kis, Csaba; Illyes, Eszter; Boros, Sandor; Kok, Robbert Jan; ?rfi, Laszlo; Bioorganic and Medicinal Chemistry Letters; vol. 28; 14; (2018); p. 2391 – 2398;,
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. 19155-24-9, name is 3,3-Dimethylindolin-2-one, A new synthetic method of this compound is introduced below., COA of Formula: C10H11NO

To a mixture of 3,3-dimethyloxindole 41 (50 mg, 0.31mmol, 1.00 equiv) and Cs2CO3 (202 mg, 0.62 mmol, 2.00 equiv) in THF (1.60 mL)was added p-nitrobenzyl bromide (101 mg, 0.47 mmol, 1.50 equiv). The reactionmixture was stirred overnight. Then, the reaction mixture was extracted with EtOAc(3 x 3 mL) and washed with brine. The combined organic phases were dried overMgSO4 and concentrated in vacuo. The residue was purified by columnchromatography (1:4 ? 1:2 EtOAc:hexanes) on silica gel to afford N?4-nitrobenzyl-3,3-dimethyloxindole 3c (77.5 mg, 84percent yield).Rf = 0.35 (1:2 EtOAc:hexanes); 1H NMR (500 MHz, CDCl3) delta 8.18 (d, J = 8.8 Hz,2H), 7.43 (d, J = 10.0 Hz, 2H), 7.25 (ddd, J = 7.3, 1.5, 0.7 Hz, 1H), 7.16 (td, J = 7.7,1.3 Hz, 1H), 7.07 (td, J = 7.5, 1.1 Hz, 1H), 6.65 (dt, J = 7.7, 0.7 Hz, 1H), 5.01 (s, 2H),1.45 (s, 6H); 13C NMR (126 MHz, CDCl3) delta 181.6, 147.6, 143.7, 141.1, 135.8, 128.0,127.9, 124.2, 123.2, 122.8, 108.7, 77.2, 44.4, 43.1, 24.7; IR (Neat Film NaCl) 2968,1707, 1613, 1522, 1343, 1173, 1111, 1009, 760; HRMS (MM: ESI-APCI+) m/zcalc?d for C17H17N2O3 [M+H]+ : 297.1234; found: 297.1239.

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; Han, Seo-Jung; Fernando De Melo, Gabriel; Stoltz, Brian M.; Tetrahedron Letters; vol. 55; 47; (2014); p. 6467 – 6469;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)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. HPLC of Formula: C10H9NO3

(i) Preparation of Ethyl-4-(2-phthalimidoethoxy)acetoacetate STR141 To a slurry of sodium hydride (57% dispersion in oil, 66.1 g; 1.57M), in tetrahydrofuran (500 ml) cooled to 0 under nitrogen was added B 2-phthalimidoethanol (150 g; 0.785M) followed by ethyl 4-chloroacetoacetate (129 g; 0.785M) in tetrahydrofuran (250 ml) over 1 hour. The mixture was stirred at room temperature overnight then poured into a mixture of 1M hydrochloric acid (800 ml) and ethyl acetate (750 ml). The organic phase was separated and the solvent was evaporated at reduced pressure. The residue separated into two layers and the upper layer of mineral oil was removed to leave the title compound (243 g) as a crude product which was used without further purification.

The synthetic route of 2-(2-Hydroxyethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US4572908; (1986); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3891-07-4,Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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.

Under nitrogen, to a cooled (0 C) solution of Ph3P (9.44 g, 36 mmol) in dry THF (60 mL), diisopropylazodicarboxylate (DIAD) (7.08 mL, 36 mmol) was added dropwise at stirring. The suspension obtained was stirred for 30 min and then a suspension of calixarene 9 (1:1 p-xylene complex, 6.40 g, 6 mmol) and 2-hydroxyethylpthalimide (6.88 g, 36 mmol) in THF (200 mL) was added dropwise. The stirring was continued for 1 h at low temperature and then for 24 h at room temperature. The reaction mixture (clear solution) was concentrated in vacuo to an oil, which was triturated with methanol. The solid formed was separated, washed with methanol and dried. Yield 89% (6.98 g, white powder). Mp 234-236 C (decomp.). 1H NMR (400 MHz, CDCl3) delta 7.93 (4H, m, ArHPht), 7.70 (4H, m, ArHPht), 6.96 (4H, s, ArH), 6.67 (4H, s, ArH), 6.65 (2H, s, OH), 4.44 (4H, t, J=6.6 Hz, NCH2), 4.24 (4H, t, J=6.6 Hz, OCH2), 4.18 (4H, d, J=2.9 Hz, ArCH2Ar), 3.25 (4H, d, J=12.9 Hz, ArCH2Ar), 2.10-1.35 (60H, m, HAd). 13C NMR (100 MHz, CDCl3) delta 168.10 (CO), 150.47, 149.01, 146.87, 141.49 (CAr), 133.83 (CHAr,Pht), 132.13, 132.09 (CAr), 127.72 (CAr,Pht), 124.96, 124.26 (CHAr), 123.22 (CHAr,Pht), 71.79 (OCH2), 43.70, 42.74 (CAd), 37.47 (NCH2), 36.91, 36.61 (CAd), 35.29, 35.26 (CAd), 31.11 (ArCH2Ar), 29.08, 28.76 (CHAd). FD-MS: m/z 1308.5 [M+H]+; C88H94N2O8·H (1308.7).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2-Hydroxyethyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Article; Vatsouro, Ivan; Serebryannikova, Alina; Wang, Leyong; Hubscher-Bruder, Veronique; Shokova, Elvira; Bolte, Michael; Arnaud-Neu, Franoise; Boehmer, Volker; Kovalev, Vladimir; Tetrahedron; vol. 67; 42; (2011); p. 8092 – 8101;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1055412-47-9, The chemical industry reduces the impact on the environment during synthesis 1055412-47-9, name is su-5614, I believe this compound will play a more active role in future production and life.

A suspension of 5-chloro-3-(1H-pyrrol-2-yl-methylene)-1,3-dihydro-indol-2-one (260 mg, 0.96 mmol), piperidine (95 muL, 0.96 mmol) and paraformaldehyde (43 mg, 1.44 mmol) in 5 mL of dioxane and 5 mL of EtOH was heated to 80 C. for 15 h. The resulting solution was cooled to room temperature followed by cooling to -20 C. for 1 h. The solid which formed was collected by filtration and rinsed with EtOH (previously cooled to -20 C.). The solid collected was dried under vacuum to give the title compound (180 mg, 51%) as a yellow-orange solid.

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, su-5614, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Allergan, Inc.; US6699863; (2004); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, molecular formula is C11H9NO3, 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. Recommanded Product: (R)-(-)-N-(2,3-Epoxypropyl)phthalimide

General procedure: Compounds 2-5 were synthesized using a modified procedure originally reported by Roehrig et al.28 To a cooled solution of (R)-(-)-N-(2,3-epoxypropyl)phthalimide 1 (102 mg, 0.50 mmol) in 10 mL of 2-propanol, amine or aminoalcohol (0.6 mmol, 1.2 equiv) in 10 mL of 2-propanol was added at 0 C and stirred for 1 h. It was then refluxed for 8 h. After the completion of the reaction, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silica gel (CHCl3/MeOH 1:20 as eluent) to afford 2-5 as white crystals.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 181140-34-1, its application will become more common.

Reference:
Article; Bozkurt, Selahattin; Durmaz, Mustafa; Naziroglu, Hayriye Nevin; Yilmaz, Mustafa; Sirit, Abdulkadir; Tetrahedron Asymmetry; vol. 22; 5; (2011); p. 541 – 549;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem