Tag: M.W=200-300

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. 959235-95-1, name is 6-(Trifluoromethoxy)indoline, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

A mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1] (2 g, 9.84 mmol), 2-(4-chlorophenyl)acetic acid [CAS 1878-66-6] (1 .85 g, 10.8 mmol), HATU (5.6 g, 14.8 mmol) and diisopropylethylamine (4.9 ml_, 29.5 mmol) in DMF (40 ml_) was stirred at room temperature for 12 h. Water was added and the precipitate was filtered off. The residue was taken up with EtOAc. The organic solution was washed with a 10% aqueous solution of K2CO3, brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel (15-40 muiotatauiota, 80 g, heptane/EtOAc gradient 90/10 to 60/40). The pure fractions were combined and the solvent was concentrated under reduced pressure to give 2-(4-chlorophenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)- ethanone 4a (3 g).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 959235-95-1.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; RABOISSON, Pierre Jean-Marie Bernard; BONFANTI, Jean-Francois; BARDIOT, Dorothee Alice Marie-Eve; MARCHAND, Arnaud Didier M; (74 pag.)WO2017/167951; (2017); A1;,
Indoline – Wikipedia,
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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 954-81-4 as follows. Formula: C13H14BrNO2

Potassium carbonate (0.50 g, 3.6 mmol) was added to a solutionof N-[(4-triphenylmethylamino)butyl]-4-nitrobenzenesulfonamide(0.93 g, 1.8 mmol) and N-(5-bromopentyl)phthalimide(0.54 g, 1.8 mmol) in DMF (12 mL). The mixture was stirred at95 C and monitored by TLC (5% EtOAc in DCM). The reactionwas diluted with ethyl acetate (100 mL) and extracted with water(4 100 mL) and brine (100 mL). The organics were dried oversodium sulfate and concentrated under reduced pressure. The residuewas purified on silica gel (1:3:96 triethylamine/ethyl acetate/dichloromethane) to yield the product as an off-white foam (1.03 g,1.41 mmol, 78%). 1H NMR (500 MHz, DMSO) d 8.35 (d, 2H, J = 9 Hz),8.02 (d, 2H, J = 9 Hz), 7.82 (m, 4H),7.35 (d, 6H, J = 8 Hz), 7.24 (t, 6H,J = 7.5 Hz), 7.13 (t, 3H, J = 7.5 Hz), 3.51 (t, 2H, J = 7 Hz), 3.07 (m, 4H),1.91 (m, 2H), 1.58 (m, 2H), 1.49 (m, 4H), 1.35 (m, 2H), 1.20 (m, 2H);13C NMR (125 MHz, CDCl3) d 168.37, 149.78, 146.04, 145.92,133.95, 132.01, 128.54, 128.16, 127.77, 126.22, 124.32,123.20,70.79, 48.22, 47.98, 42.99, 37.47, 28.08, 27.99, 27.82,26.44, 23.78; HRMS (C42H42N4O6S): calculated 730.2825, observed730.2837

According to the analysis of related databases, 954-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Thomson, Andrew; O’Connor, Sean; Knuckley, Bryan; Causey, Corey P.; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4602 – 4608;,
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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. 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4,7-Dichloroindoline-2,3-dione

General procedure: alpha-Isothiocyanato imide 2c (10.7 mg, 0.050 mmol) and catalyst 6d (2.8 mg, 0.005 mmol, 10 mol %) were dissolved in diethyl ether (1.0 mL) in a glass vial while stirring. Isatin 1a (8.8 mg, 0.060 mmol) was added and the mixture was further stirred at room temperature for 2 h. The reaction progress was monitored by TLC analysis. Upon completion, the solvent was removed under reduced pressure and the crude product was purified by flash column chromatography on silica gel (1:1 hexane/ethyl acetate) to give the desired product.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 18711-13-2.

Reference:
Article; Guang, Jie; Zhao, Cong-Gui; Tetrahedron Asymmetry; vol. 22; 11; (2011); p. 1205 – 1211;,
Indoline – Wikipedia,
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Reference of 5332-26-3, 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 5332-26-3 as follows.

General procedure: To a mixture of substituted benzyl bromide 3a-3o (1.0 mmol), sodium azide (3.0 mmol), alkyne 2 (1.0 mmol) in DMF/water (8:2), copper sulfate pentahydrate (10 mol%) and sodium ascorbate (20 mol%) were added. The reaction mixture was stirred for 4-16 h at room temperature, and the progress of the reaction was monitored by TLC. After completion of the reaction, ice-cold water (30 mL) was added to the reaction mixture. The residue thus obtained was filtered, washed with aqueous ammonium chloride/ammonia (9:1) solution and water and recrystallized with chloroform/hexane (8:2) to get 1,4-disubstituted 1,2,3-triazoles (4a-4o).

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lal, Kashmiri; Yadav, Pinki; Kumar, Ashwani; Medicinal Chemistry Research; vol. 25; 4; (2016); p. 644 – 652;,
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. Product Details of 20780-72-7

General procedure: A solution of 2-nitrobenzamides 1 or bis(2-nitrobenzamides) 4 (1 mmol), isatins 2 or acenaphthylene-1,2-diones 6 (1 mmol), and SnCl2*2H2O (4 mmol) in EtOH (5 mL) was stirred at reflux for 3-5 h. After this period, the TLC analysis of the mixture showed the reaction to be completed. The mixture was quenched with 3percent HCl (10 mL) and filtered to yield a crude product, which was purified by recrystallization from 95percent ethanol and DMF.

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

Reference:
Article; Hu, Yu; Wang, Man-Man; Chen, Hui; Shi, Da-Qing; Tetrahedron; vol. 67; 48; (2011); p. 9342 – 9346;,
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: A mixture of isatin (1) (2.0 mmol), L-proline (2) (2.0 mmol) and acrylonitrile/methyl acrylate (3/5) (2.0 mmol) in 10 mL of water was heated in an oil bath at 80 C for 3 to 6 hours. Initially reaction mixture appeared to be homogeneous but with the progress of reaction the solid precipitated out. TLC indicated the consumption of L-proline and acrylonitrile while isatin was remaining in small portion. The reaction mixture was extracted many times with ethylacetate (EA). The combine organic layer was dried over anhydrous Na2SO4 and evaporated on rotary evaporator to provide yellow colour solid. The solid was purified by silica gel column chromatography using EA:hexane (4:6) as an eluent to provide desired product 4 and 6 as white solid. The yield mentioned in the analytical data has been calculated after recovering the unreacted isatin (amount mentioned in characterization data).

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

Reference:
Article; Tiwari, Keshri Nath; Pandurang, Taur Prakash; Pant, Suyash; Kumar, Rahul; Tetrahedron Letters; vol. 57; 21; (2016); p. 2286 – 2289;,
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.

General procedure: To a vial containing 5b (12 mg, 0.05 mmol), TFA (11 mg,0.1 mmol) and EtOH (2.0 mL) was added 4-nitrobenzaldehyde (76 mg, 0.50 mmol). The reaction mixture was stirred for 5 min, then cyclohexanone (147 mg, 1.50 mmol) was added. The resulting mixture was stirred at room temperature for 24 h until the reaction was complete by monitoring (TLC). Next, saturated NH4Cl solution and ethyl acetate were added with vigorous stirring. The organic phase was separated, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was then purified by column chromatography on silica gel (mixture of ethyl acetate/hexane) to give the corresponding aldol adducts. The anti/syn ratio (diastereoselectivity) and ee values (enantioselectivity) were determinedby HPLC on a chiral column.

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

Reference:
Article; Li, Lei; Gou, Shaohua; Liu, Fei; Tetrahedron Asymmetry; vol. 25; 2; (2014); p. 193 – 197;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 5332-26-3, 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of the tetrabutylammonium salt of 10-methylthio-7,8-dicarba-nido-caborane [1] (0.40 g, 0.95 mmol) in ethanol (10ml) chloroacetonitrile (0.06 ml, 0.95 mmol) was added. After stirring for 15 min, r.t., the mixture was heated under reflux for about 15 h and the solvent was evaporated under reduced pressure. The column chromatography on silica gel was used for the purification of the substance with CH2Cl2 as an eluent. Finally the solvent was removed in a vacuum to yield white solid (0.14 g, 68% yield).

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

Reference:
Article; Erokhina, Svetlana A.; Stogniy, Marina Yu.; Suponitsky, Kyrill Yu.; Kosenko, Irina D.; Sivaev, Igor B.; Bregadze, Vladimir I.; Polyhedron; vol. 153; (2018); p. 145 – 151;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 104618-31-7, 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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-[4-(1,3-Dioxo-1 , 3-dihydro-isoindol-2-yl)-cyclohexyloxy]-benzoic acid ethyl ester; To a stirred solution of 2-(4-hydroxycyclohexyl)isoindole-1 ,3-dione (8.0 g, 32.6 mmol) in dry THF (100 ml.) was added triphenyl phosphine (12.8 g, 48.8 mmol) and 4- hydroxy benzoic acid ethyl ester (5.44 g, 32.7 mmol). The reaction mixture was cooled to 0 0C and DIAD (9.6 g, 47.4 mmol) was added dropwise from an addition funnel over a period of 3 h. The reaction was gradually brought to room temperature and stirring continued for 3 h. The solvent was removed under vacuum and ether (100 ml.) was added and cooled to 0 0C. The solid formed was filtered and the clear filtrate concentrated and purified by column chromatography over neutral alumina (8 % AcOEt in hexane) to give 5.13 g (42 %) of 4-[4- (I .S-dioxo-I .S-dihydro-isoindol^-ylJ-cyclohexyloxyJ-benzoic acid ethyl ester. 1H-NMR (300 MHz, CDCI3); delta 1.24 – 1.36 (m, 2H), 1.40 (t, 3H), 1.63 – 1.77 (m, 3H), 2.19 – 2.29 (m, 2H), 2.62 – 2.79 (dq, 2H), 4.15 – 4.72 (m, 1 H), 4.35 (q, 2H), 7.01 (d, 2H), 7.71 (m, 2H), 7.82 (m, 2H), 8.0 (d, 2H). m/z: 394.1 (M+1 )+

The synthetic route of 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVO NORDISK A/S; WO2007/115935; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6326-79-0, 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. 6326-79-0 name is 6-Bromoisatin, 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.

The mixture of IX-1 (6.5 g, 28.7 mmol), malonic acid (3.3 g, 31.7 mmol), NaOAc (2.95 g, 36 mmol) in AcOH (60 mL) were stirred at rt. After 6 hrs, NaOAc (2.95 g, 36 mmol) was added additional, then refluxed overnight. After cooling, the mixture was filtered and the filtrate was washed with water and EtOAc, then dried under reduced pressure to afford IX-2 (5 g, yield 66%) as a brown oil, which was used for next step directly.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromoisatin, and friends who are interested can also refer to it.

Reference:
Patent; Buckman, Brad Owen; Nicholas, John Beamond; Emayan, Kumaraswamy; Seiwert, Scott D.; US2014/200215; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem