Tag: M.W=200-300

Application of 169037-23-4, These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-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.

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 169037-23-4 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,
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Some common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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. Computed Properties of C8H6BrNO

Step 3: 5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one 5-Bromo-2,3-dihydro-isoindol-1-one (230 mg, 1.08 mmol), bis(pinacolato)diboron (300 mg, 1.18 mmol), PdCl2dppf (25 mg, 31 mumol) and KOAc (320 mg, 3.26 mmol) are suspended in dioxane (4 ml), purged with nitrogen for 5 minutes and then heated at 85 C. overnight. The solvent is removed in vacuo and the residue partitioned between ethyl acetate and water. The aqueous layer is extracted three times with ethyl acetate and the combined organic phases are washed once with brine, filtered through anhydrous MgSO4 and evaporated. The solid residue is triturated with hexane and dried in vacuo to furnish the title compound (185 mg, 66%) as a grey solid. 1H-NMR (400 MHz, CDCl3) delta (ppm) 1.37 (s, 12H, 4*CH3), 4.45 (s, 2H, CH2), 6.38 (bs, 1H, NH), 7.87 (d, 1H, H), 7.93 (m, 2H, H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 552330-86-6, its application will become more common.

Reference:
Patent; Andrews, Martin James Inglis; Chambers, Mark Stuart; Van De Poel, Herve; Bar, Gregory Louis Joseph; US2009/286798; (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. 20870-78-4, name is 5-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 5-Bromoindolin-2-one

General procedure: An oven-dried flask was charged with stir bar, oxindole (0.5 mmol), PIDA (0.25 mmol) in dry acetonitrile (4.0 mL). Then to the reaction mixture TEMPO (0.5 mmol) was added in presence of air and the mixture was stirred at room temperature until complete conversion takes place as indicated by TLC analysis. The resulting reaction mixture was extracted with ethyl acetate (3 10 mL). The combined organics were dried with Na2SO4 and dried under vacuum to afford crude solid. Then the crude product was purified by column chromatography on silica gel.

The synthetic route of 20870-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sai Prathima, Parvathaneni; Bikshapathi, Raktani; Rao, Vaidya Jayathirtha; Tetrahedron Letters; vol. 56; 46; (2015); p. 6385 – 6388;,
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 181140-34-1 as follows. Recommanded Product: 181140-34-1

A mixture of 2,3-dihydro-1 /-/-inden-2-amine (5.0 g, 24.61 mmol) and (R)-2-(oxiran-2- ylmethyl)isoindoline-1 ,3-dione (4.91 g, 36.91 mmol) in EtOH (100 mL) was heated at reflux overnight. After cooling to room temperature, triethylamine (9.94 g, 98.44 mmol) and (0472) (Boc)20 (10.74 g, 49.22 mmol) were added and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated and purified by column (EtOAc / petroleum ether = 1/4, v/v) to give the title compound (5.4 g, 50%) as an oil.

According to the analysis of related databases, 181140-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CTXT PTY LIMITED; STUPPLE, Paul Anthony; (88 pag.)WO2017/153519; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 552330-86-6, A common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

Prepared using method described in Example 4, step (a) with the solution being initially irradiated for 90 min and then a further 90 min using 5-cyclopropyl-6-methyl-7-(tetramethyl- 1 ,3,2-dioxaborolan-2yl)-oxazolo[4,5-c]quinolin-4-one (Intermediate D) and 5-bromo-2,3- dihydro-1 H-isoindol-1-one. Chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1 , 1 ‘- biphenyl)[2-(2’-amino-1 , 1 ‘-biphenyl)]palladium(ll) (10% mmol) was used as catalyst and .2- dicyclohexylphosphino-2′,4′,6’-triisopropylbiphenyl (10% mmol) as ligand. Column chromatography was carried out, eluting with 0-20% MeOH in DCM. 1 H NMR (Method A) (CDCb): delta ppm 8.10 (s, 1 H), 7.99 (d, J = 7.8 Hz, 1 H), 7.81 (d, J = 7.9 Hz, 1 H), 7.53 (d, J = 8.0 Hz, 1 H) 7.50 (s, 1 H), 7.28 (s, 1 H), 6.22 (s, 1 H), 4.56 (s, 2H), 3.69- 3.61 (m, 1 H), 2.54 (s, 3H), 1.33 (d, J = 6.8 Hz, 2H) 0.74 – 0.66 (m, 2H); LC-MS (Method D) 372.0 [M+H]+; RT 1.96 min

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; REDX PHARMA PLC; HUXLEY, Anthony; KIRK, Ralph; RATCLIFFE, Andrew; LYTH, David; (112 pag.)WO2017/46605; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 954-81-4, 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. 954-81-4 name is N-(5-Bromopentyl)phthalimide, 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.

To a stirred solution of compound 14-k (80 g, 0.27 mol) in DMF (745 mL) was added potassium thioacetate (34 g, 0.29 mol) portion wise over 20 mm at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 mm. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (1 L) and stirred for 1 h. The resultant precipitate was filtered, washed with water (500 mL) and dried in vacuo to afford 15-k as an off-white solid (75 g, 95%).?HNMR (400 IVIFIz, CDC13): 7.84 (dd, J= 5.5 Hz, 3.0 Hz, 2H), 7.71 (dd, J 5.5 Hz, 3.1 Hz, 2H), 3.67 (t, J= 7.3 Hz, 2H), 2.85 (t, J= 7.3 Hz, 2H), 2.30 (s, 3H), 1.73-1.65 (m, 3H), 1.64-1.57 (m, 1H), 1.46-1.37 (m, 2H);LC-MS: 292.2 (M+1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-(5-Bromopentyl)phthalimide, and friends who are interested can also refer to it.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LADNER, Robert, D.; (340 pag.)WO2018/98207; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 18711-15-4, name is 4,6-Dichloroisatin, 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. category: indolines-derivatives

Reference Example 23 4,6-Dichloro-3-hydroxy-3-(2-naphthyl)oxindole To a solution of 2-bromonaphthalene (2.952 g) in anhydrous THF (25 mL) was added portion wise a solution of n-butyl lithium in n-hexane (1.55 N, 10.12 mL) at -78 C. The reaction solution was stirred for 30 minutes. To the mixture was then added portion wise a solution of 4,6-dichloroisatin (1.54 g) in anhydrous THF (25 ml) for 50 minutes. The reaction mixture was stirred for 2 hours. Then the mixture was allowed to warm to room temperature. To the mixture was added 1N HCl and extracted by ethyl acetate. The organic phase was separated, washed with 1N HCl and brine and dried over MgSO4 and concentrated. Purification was carried out by silica gel chromatography (hexane:ethyl acetate, 2:1 to 1:1 gradient) to give the title compound (0.652 g, yield: 27%). 1H NMR (DMSO-d6, 300 MHz) delta 6.93 (1H, s), 6.96 (1H, d, J=1.7 Hz), 7.12 (1H, d, J=1.7 Hz), 7.23 (1H, m), 7.49 (2H, m), 7.80-7.94 (4H, m), 10.80 (1H, brs).

The synthetic route of 4,6-Dichloroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Pharmaceuticals Co., Ltd.; US6576656; (2003); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 20780-72-7,Some common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, molecular formula is C8H4BrNO2, 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.

A mixture of 1.0 g (4.4 mmol) of 4-bromoindole diketone,Methyl acrylate (0.46 g, 5.3 mmol)PdCl2 (PPh3) 20.15 g (0.22 mmol),K3PO41.6 g (6.2 mmol),Into the microwave reaction flask,Add 5 mL of DMF,Argon protection,And reacted at 145 ° C for 30 min in a microwave reactor.TLC detection reaction is complete,The reaction solution was washed three times with 100 mL of saturated brine,Extracted with dichloromethane,Combined organic phase,Dried over anhydrous sodium sulfate and purified by silica gel column chromatography using developing solvent petroleum ether: ethyl acetate = 5: 1-1: 1,200-300 mesh,4-methyl acrylate indole diketone 0.65 g, yield 64percent.

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

Reference:
Patent; Tianjin Kunjian Bio-pharmaceutical Co., Ltd.; Yu Peng; Han Kailin; Mao Huihua; Qiu Dongxu; (8 pag.)CN104370799; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 104618-31-7, The chemical industry reduces the impact on the environment during synthesis 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

190gms(0.7755mole) 4-phthalimido cyclohexanol are dissolve in 1480ml chloroform.Add solution of H2SO4 (435.87gm, 4.4476mole cone. H2SO4 was added in 900 mlwater). Cool mass to 25C,add lot wise 180.5gm(0.6139mole) potassium dichromate inone hour. Stir mass for three hours, add 900 ml water and separate organic phase.Organic phase was washed with water and 2% NaHCO3 solution, after drying andconcentration of extracts product was isolated by adding methanol and water mixture.YIELD: 175g(92.4%)PURITY: 96.01%.

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, 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALEMBIC LIMITED; WO2006/3677; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 15362-40-0, The chemical industry reduces the impact on the environment during synthesis 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, I believe this compound will play a more active role in future production and life.

General procedure: Compounds 4-9 were prepared through knoevenagel condensation of compounds 12 and 13 (1 mmol) with active methylene compounds including 1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one, oxindole and indolinone (1 mmol). The reactants were heated at 160-180 C for about 10-20 min in oil bath and the completion of the reaction was monitored using TLC. The crude products were solidified by triturating with diethyl ether and purified by recrystallization and column chromatography.

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, 1-(2,6-Dichlorophenyl)-2-indolinone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Singh, Palwinder; Shaveta; Sharma, Surbhi; Bhatti, Rajbir; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 77 – 82;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem