Tag: M.W=200-300

Application 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: To a stirred mixture of 1-benzyl-1H-indole-2,3-dione (1a, 0.25 g,1.05 mmol), CuI (0.01 g, 0.05 mmol, 0.05 equiv), and phenylacetylene (2a, 0.11 g, 1.11 mmol, 1.05 equiv) in anhyd toluene (2 mL), DBU (0.032 g, 0.21 mmol, 0.2 equiv) was added at 25 C under a N2 atmosphere. Stirring was continued at this temperature until the starting material was completely consumed (TLC monitoring). After completion, the mixture was quenched with sat. aq NH4Cl (2mL) and extracted with EtOAc (2 ¡Á 5 mL). The combined organic layers were dried (anhyd Na2SO4) and evaporated under reduced pressure to dryness. The crude product thus obtained was purified by column chromatography (activated silica gel, 60-120 mesh, hexane-EtOAc) to afford pure 3aa as a white solid; yield: 0.35 g (97%); mp 177-179 C.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chouhan, Mangilal; Senwar, Kishna Ram; Kumar, Kapil; Sharma, Ratnesh; Nair, Vipin A.; Synthesis; vol. 46; 2; (2014); p. 195 – 202;,
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 99365-40-9 as follows. Formula: C8H6BrNO

Under an argon atmosphere NaH (60 % on mineral oil, 7.32 g) was suspended in dry THF (45 ml). A suspension of 6-bromoindolin-2-one (10.0 g) in dry THF (108 ml) was added in portions during 10 min keeping the temperature below 27 C. The reaction mixture was warmed to 25 C, Mel (11.4 ml) was added drop wise during 1 h while the internal temperature was carefully kept between 24 and 27 C and stirring was continued for 18 h. Saturated aqueous NH4C1 solution (20 ml) was carefully added at 10-15 C, the mixture was diluted with EtOAc and saturated aqueous NaHC03 solution, the organic layer was washed with saturated aqueous NaHC03 solution, dried and evaporated. The residue was purified by flash chromatography (siliga gel, gradient 0% to 30% EtOAc in n-heptane) to give the title compound (10.1 g, 84%) as a light red solid. MS (ESI, m/z): 254.1/256.2 [(M+H)+].

According to the analysis of related databases, 99365-40-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; LIMBERG, Anja; STOLL, Theodor; WO2015/177110; (2015); 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 169037-23-4 as follows. Formula: C9H4F3NO3

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.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

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

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. 6326-79-0, name is 6-Bromoisatin, A new synthetic method of this compound is introduced below., Recommanded Product: 6326-79-0

Step 1: Synthesis of Intermediate 1-12.1 To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 niL, 241 mmol) and K2C03 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgS04 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001 004.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter, Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; BINDER, Florian; VINTONYAK, Viktor; WO2014/140075; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common compound: 99365-40-9, name is 6-Bromoindolin-2-one, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 99365-40-9

Di-tert-butyl dicarbonate (4.63 g, 21.2 mmol) and sodium hydrogen carbonate (10.7 g, 127 mmol) were added to a stirred solution of 6-bromoindolin-2-one (preparation 1, 3.0 g, 14.2 mmol) in tetrahydrofuran (150 mL) and the mixture was heated to reflux. After 3 hours the mixture was cooled and filtered and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (10:1 hexanes/ethyl acetate) gave the title compound (3.58 g, 81%) as a white solid. LRMS (m/z): 312/314 (M+1)+. 1H-NMR delta (CDCl3): 1.65 (s, 9H), 3.66 (s, 2H), 7.10(d, 1H), 7.27 (d, 1H), 8.03 (s, 1H).

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, 99365-40-9, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2113503; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

20870-90-0, Adding a certain compound to certain chemical reactions, such as: 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, 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 20870-90-0.

A mixture of 5-bromo-N-methyloxindole(5 g, 22 mmol) and POCl3 (40 mL) was stirred and refluxed for 2h. After cooling, themixture was poured into ice water, and then extracted with dichloromethane (MC) forthree times. The combined organic layers were dried over anhydrous magnesium sulfate,filtered, and concentrated. The solid was washed with MC, white solid NMT (2.6 g) wasprepared. Yield was 61%.1H-NMR (300MHz, THF) delta(ppm) : 8.58 (s, 3H), 7.63-7.60 (d, 3H), 7.57-7.53 (d, 3H),4.40 (s, 9H).

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, 5-Bromo-1-methyl-2-oxoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kang, Hyeonmi; Lee, Hayoon; Shin, Hwangyu; Kang, Seokwoo; Kim, Beomjin; Park, Jongwook; Molecular Crystals and Liquid Crystals; vol. 618; 1; (2015); p. 47 – 54;,
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 2058-72-2 as follows. 2058-72-2

General procedure: solution of isatin (1a) (0.3 gm, 2.04 mmol),proline (2) (0.234 gm, 2.04 mmol) and methyl vinyl ketone (3) (255 muL, 3.00 mmol) in CH3CNwas heated to 80 C for 2 h. After the completion of starting precursor, the reaction mixture wascooled and solvent was evaporated on rotator evaporator to provide brown solid. The reactionmixture was purified by silica gel chromatography using hexane:ethyl acetate (6:4) as an eluentto provide product (4a) as a white solid

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tiwari, Keshri Nath; Pandurang, Taur Prakash; Pant, Suyash; Sreelekha; Synthetic Communications; vol. 48; 7; (2018); p. 802 – 808;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

The chemical industry reduces the impact on the environment during synthesis 143262-20-8, name is 1-(tert-Butoxycarbonyl)indoline-7-carboxylic acid, I believe this compound will play a more active role in future production and life. 143262-20-8

Step 3: Methyl 4-{ l-[(2,3-dihydro-lH-indol-7-ylcarbonyl)amino]cyclopropyl}benzoatel-(te^butoxycarbonyl)indoline-7-carboxylic acid (300 mg, 1.14 mmol), HATU (475 mg, 21.2 mmol) and methyl 4-(l-aminocyclopropyl)benzoate (262 mg, 1.37 mmol) were added to acetonitrile (7.6 ml). The solution was cooled in an ice bath and DIPEA (695 ul, 3.99 mmol) was added. After 2 hr at RT, the mixture was poured into a solution OfNaHCO3 (l/2sat.) and washed 3 times with EtOAc. The combined organic layers were washed with brine and dried with Na2SO4. The solvent was removed and the crude mixture purified by flash chromatography on silica gel. The Boc group was removed with 1:1 TFA/DCM using the standard procedure.

The chemical industry reduces the impact on the environment during synthesis 143262-20-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2008/104055; (2008); 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., 169037-23-4

General procedure: A mixture of beta-nitrostyrenes, isatin and tyrosine (1:1:1) was stirredunder heating at 100 C for 1 h in [bmim]Br (200 mg). After the reaction was completed, 10 mL of ethyl acetate was added to the reaction mixture and stirred for 15 min. The organic layer was separated, washed with water, and dried. The cycloadduct was further purified using hexane: ethyl acetate (3:2 v/v) as eluent employing column chromatography technique. After extraction of the cycloadduct, [bmim]Br wasdried under vacuum at 80 C for 2 h to exclude any water trapped from moisture and reused for subsequent runs.

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; Kumar, Raju Suresh; Almansour, Abdulrahman I.; Arumugam, Natarajan; Mohammad, Faruq; Kotresha; Menendez, J. Carlos; Bioorganic and Medicinal Chemistry; vol. 27; 12; (2019); p. 2487 – 2498;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

70478-63-6, The chemical industry reduces the impact on the environment during synthesis 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

A mixture of 3-bromophthalimide (10.0 g, 44.2 mmol), potassium carbonate (12.2 g, 88.5 mmol) and potassium iodide (50 mg, 0.30 mmol) are stirred in 80 mL DMF for 15 min. The reaction mixture is cooled to 0 0C, methyl iodide (3.04 mL, 48.7 mmol) is added and the reaction mixture is stirred overnight at RT. The reaction mixture is filtered, the solids are washed with DMF and the filtrate is poured in water. The mixture is extracted with ethyl acetate and the combined organic phases are washed several times with water, dried over MgSO4 and concentrated in vacuo. Yield: 7.10 g.

The chemical industry reduces the impact on the environment during synthesis 4-Bromoisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/112565; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem