Tag: M.W=200-300

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. 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-(3-Oxobutyl)isoindoline-1,3-dione

A solution of 4-(3-piperidin-4-yl-3-thiophen-3-ylmethyl-ureidomethyl)-benzoic acid methyl ester (97 mg, 0.25 mmol), 2-(3-oxo-butyl)-isoindole-l,3-dione (109 mg, 0.50 mmol) and glacial AcOH (5 drops) in MeOH (1.2 ml) at 60 C was added NaBH3CN (50 mg, 0.80 mmol) and the reaction was stirred for 20.5 hours. The reaction was cooled, diluted with saturated aqueous NaHCO3 (25 ml) and was extracted with CH2Cl2 (20 ml X 3). The combined organic solution was dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash column chromatography on silica (CH2Cl2/MeOH, 29:1) gave the tertiary piperidine as a white foam (86.3 mg, 59%). 1H NMR (CDCl3) delta 0.95 (d, 3H, J= 6.2 Hz), 1.18-1.71 (m, 5H), 1.84-1.97 (m, IH), 2.09-2.20 (m, IH), 2.40-2.50 (m, IH), 2.63-2.83 (m, 3H), 2.64-2.88 (m, 2H), 3.89 (s, 3H), 4.11 (s, 2H), 4.19-4.31 (m, IH), 4.36 (d, 2H, J= 5.3 Hz), 4.69 (t, IH, J= 5.3 Hz), 6.92 (d, IH, J= 5.1 Hz), 7.04 (s, IH), 7.09 (d, 2H, J= 8.4 Hz), 7.33 (dd, IH, J= 5.1, 3.1 Hz), 7.57-7.63 (m, 2H), 7.75-7.81 (m, 2H), 7.90 (d, 2H, J= 8.4 Hz).

The synthetic route of 3783-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ANORMED INC.; WO2006/138350; (2006); A2;,
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. 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 6-Bromo-1-methylindoline-2,3-dione

1-3. I (JS.O g, 63 nunol) and hydrazine hydrate (30 mL, 618 nunol) are heated to 12S C for 72 h.To the cool reaction mixtw-e DCM is added and extracted with water and 1 M HCI. The organiclayer is dried over MgS04 and concentrated. The crystaJlized residue is dissolved in DCM,methanol is added and the DCM is removed in vacuo. The crystallized product is filtered by sunction and washed with cold methanol. Yield 63%, mz 226/228 [M+H]+, rt J.l6 min, LC-MSMethod VOOJ 003.

The synthetic route of 667463-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRAUERT, Matthias; ANDERSKEWITZ, Ralf; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140081; (2014); 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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Formula: C8H4BrNO2

To a solution of 4a (10 g, 44.4 mmol) in TRF (200 mE) was added NaI3R4 (17.6 g, 464.8 mmol), followed by 13F3.Et20 (170 ml, 519.2 mmol) drop- wise at room temperature. The mixture was then heated at 80 C. overnight, cooled to 0 C. and adjusted to pH 13 with aqueous NaOH solution. The mixture was extracted with ethyl acetate (100 mEx3). The combined organic phase was washed with water, brine and dried over anhydrous Na2504. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (DCM:MeOR=10:1, v: v) to provide 4b (7.3 g, 83% yield). EC-MS: 198 [M+1].

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:
Patent; HELSINN HEALTHCARE SA; Giuliano, Claudio; Daina, Antoine; Pietra, Claudio; (254 pag.)US2017/275301; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, 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.

Intermediate 60 : 2-(3-(3-Oxopiperazin-l-yl)propyl)isoindoline-l,3-dione (0587) A mixture of 3-(l,3-dioxoisoindolin-2-yl)propanal (499.4 mg, 2.458 mmol, commercially available from Fluorochem), piperazin-2-one (376.1 mg, 3.76 mmol, commercially available from Sigma Aldrich) and Na(0Ac)3BH (779.9 mg, 3.68 mmol) in 2-MeTHF (20 mL) was stirred at rt for 21 h 40 min. Further Na(OAc)3BH (516.6 mg, 2.437 mmol) was added after 3 h. AcOH (0.014 mL, 0.246 mmol) was added after 4 h 45 min. After 20 h 40 min further 2-MeTHF (5 mL) was added and the reaction mixture was heated to 60 C. Further Na(OAc)3BH (279.9 mg, 1.321 mmol) was added after 3 h 20 min at 60 C. Further Na(OAc)3BH (496.8 mg, 2.344 mmol) was added after 25 h 45 min at 60 C. The mixture was removed from heating and stirring after a total of 31 h at 60 C and cooled to rt. To this mixture was added sat. NaHCCte (2 mL) and water (8 mL). The mixture was stirred at rt for 20 min and extracted with EtOAc (3 x 10 mL). The organic layer was filtered through a cartridge fitted with a hydrophobic frit and the volatiles evaporated in vacuoto give an oil which was redissolved in MeOH (approx. 5 mL) and applied to the top of a 20 g Isolute aminopropyl ion exchange column. The column was eluted with 4 column volumes of MeOH and 4 column volumes of aqueous 2M HCI. The second MeOH fraction was evaporated in vacuoto give a pale yellow solid; 2-(3-(3-oxopiperazin- l-yl)propyl)isoindoline-l,3-dione (595.1 mg, 2.071 mmol, 84 % yield). (0588) LCMS (2 min high pH); Rt = 0.71 min, m/z = 288 for [MH]+

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; ATKINSON, Stephen John; DEMONT, Emmanuel Hubert; HARRISON, Lee Andrew; LEVERNIER, Etienne; PRESTON, Alexander G; SEAL, Jonathan Thomas; WALL, Ian David; WATSON, Robert J; WOOLVEN, James Michael; (225 pag.)WO2017/174621; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 100510-64-3 as follows. Formula: C10H10N2O3

B. 6-Amino-3,3-dimethylindolin-2-one A mixture of 3,3-dimethyl-6-nitroindolin-2-one (500 mg, 2.4 mmol), 10% Pd-C (100 mg), and MeOH (100 mL) was stirred under H2 (1 atm) for 3 h. After that the catalyst was filtered off and the filtrate was concentrated to give an off-white solid (420 mg). MS: M+H=177.3

According to the analysis of related databases, 100510-64-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kelly, Michael G.; Janagani, Satyanarayana; Wu, Guoxian; Kincaid, John; Lonergan, David; Fang, YunFeng; Wei, Zhi-Liang; US2005/277643; (2005); 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. 20780-72-7, name is 4-Bromoisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H4BrNO2

General procedure: Isatin 1 (1 mmol), active methylene 2 (1 mmol), phosphite 3 (1mmol), and [DABCO-H][AcO] (17.2 mg, 0.1 mmol) were added to THF(0.3 mL). Then the reaction mixture was vigorously stirred at r.t. Theprogress of the reaction was monitored by TLC (n-hexane?EtOAc,4:1). After completion of the reaction, cold H2O (2 mL) was added. TheIL catalyst dissolved in the H2O and the insoluble crude products wereisolated by simple filtration. The crude products were recrystallizedfrom EtOH to afford pure final products. After removal of the H2O underreduced pressure, the catalyst [DABCO-H][AcO] could be directlyreused for the next run under similar reaction conditions.

The synthetic route of 20780-72-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Song, Lan-Lan; Yang, Cheng; Yu, Ya-Qin; Xu, Da-Zhen; Synthesis; vol. 49; 7; (2017); p. 1641 – 1647;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: (2E,2’E)-3,3′-Benzene-1,4-diylbis(1-phenylprop-2-en-1-one) (1) (0.34 g, 1 mmol) was added in one portion at room temperature to a stirred solution of isatin 2(1 mmol) and sarcosine (4) (0.09 g, 1 mmol) in 10 ml ethanol. The reaction mixture was stirred for 8 h. The solvent was then removed under reduced pressure, and theresidue was recrystallized from ethyl acetate as white powder.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Taghizadeh, Mohammad Javad; Javidan, Abdollah; Keshipour, Sajjad; Chemistry of Heterocyclic Compounds; vol. 51; 5; (2015); p. 467 – 471; Khim. Geterotsikl. Soedin.; vol. 51; 5; (2015); p. 467 – 471,5;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 99365-40-9, 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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The reaction condition is three: under the protection of nitrogen, the 6 – bromo indole -2 – ketone (212.0 mg, 1.0 mmol), potassium carbonate (276 mg, 2 mmol), tetrabutyl ammonium bromide (33 mg, 0.1 mmol) is placed in the dual-port reaction bottle. The good sealing of the reaction device, replacing the nitrogen three times, nitrogen balloon is inserted. Injection 22 ml tetrahydrofuran, in 85 C under stirring conditions for 30 min, then slowly injected into the 3 ml bromo hexane, maintain 85 C under stirring 8 h. To be reaction slowly cooling to the room temperature after quenching in the into ice water, dichloromethane is used for extracting the organic phase, deionized water after washing three times, the organic phase for water-free magnesium sulfate drying. After filtering the organic phase by the vacuum concentrated under reduced pressure to get the crude product, using column chromatography (eluate to DCM/PE=1:1) purification, to obtain white waxy solid compound 1 – hexyl -6 – bromo – indolone (172 mg), yield 58.1%.

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, 6-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing University of Posts and Telecommunications; Lai Wenyong; Meng Cheng; Li Xiangchun; Huang Wei; (19 pag.)CN108794494; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: C9H6BrNO2

General procedure: A mixture of substituted isatin 1 (0.5 mmol), cyclic 1,3-dicarbonyl 2 (0.55 mmol), 4-hydroxyl coumarin 3 (0.55 mmol) and I2 (0.05 mmol) in DCE (2 mL) was heated at 60 C under atmosphere. The progress was monitored using TLC detection. After completion of the present reaction, the reaction mixture was concentrated under vacuum. The residue was purified by column chromatography [eluent, petroleum ether/ethyl acetate 5:1] to afford the desired products 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2058-72-2, its application will become more common.

Reference:
Article; Zhang, Min; Yang, Wenbo; Qian, Min; Zhao, Ting; Yang, Liuqing; Zhu, Chunyin; Tetrahedron; vol. 74; 9; (2018); p. 955 – 961;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 22949-08-2,Some common heterocyclic compound, 22949-08-2, name is 1-(6-Nitroindolin-1-yl)ethanone, molecular formula is C10H10N2O3, 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 B: l-Acetyl-6-nitroindoline (3.8 g, 18.3 mmol) was suspended in EtOAc (200 mL). Pd/C (650 mg, 10%) was added, and the mixture was hydrogenated at 40-55 p.si.i. for 2 hours. The mixture was then filtered through celite. The filtrate was concentrated, and the residue was triturated with ether to yield l-acetyl-6-aminoindoline (3.18 g, 99%) as an orange solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(6-Nitroindolin-1-yl)ethanone, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; HWANG, Peter Seongwoo; TAKASUGI, James; REN, Hongyu; WILDE, Richard Gerald; TURPOFF, Anthony; AREFOLOV, Alexander; KARP, Gary Mitchell; CHEN, Guangming; CAMPBELL, Jeffrey Allen; WO2006/19831; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem