Author: Jessica.F

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. 7477-63-6, name is 7-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H4ClNO2

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

The synthetic route of 7477-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

261732-38-1, name is tert-Butyl 5-bromoindoline-1-carboxylate, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of tert-Butyl 5-bromoindoline-1-carboxylate

Part 2. To a solution of N-Boc-5-bromoindoline (104 mg, 0.35 mmol) in 5 ml of anhydrous dioxane were added the boronic acid from Example 19 (100 mg, 0.39 mmol), cesium carbonate (228 mg, 0.7 mmol) and tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct (10 mg, 0.01 mmol). The reaction flask was thoroughly flushed with argon, and tri-tert-butylphosphine (0.006 mL, 0.025 mmol) was added via syringe. The reaction was heated to 80 C. and stirred overnight. The reaction was then cooled to room temperature, diluted with 25 mL of diethyl ether, flushed through a pad of Celite and concentrated in vacuo to give a brown residue. This residue was subjected to flash column chromatography on silica gel using 25% ethyl acetate in hexane to give the desired biphenylamine (150 mg, 100%) as a light brown oil after drying. 1H NMR (CDCl3) delta: 1.02 (s, 9H); 1.22 (s, 9H); 3.10-3.15 (t, 2H); 4.02, (t, 2H); 7.25-8.14 (m, 7H).

The synthetic route of 261732-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US6534535; (2003); B1;,
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Indoline | C8H9N – PubChem

Related Products of 14192-26-8, 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To N, N-dimethylformamide (1000 ml) were added methyl 2-oxindole-6-carboxylate (100.0 g), benzoic acid methyl ester (78.3 g) and potassium carbonate (180.7 g) were added and stirred at room temperature for 3 hours. N- (4-aminophenyl) -N-methyl-2- (134.5g). After stirring at room temperature for 4 hours, the reaction mixture was poured into water (3000ml), stirred for 30 minutes, filtered and recrystallized from methylene chloride / methanol (10: 4 by volume) and dried to give 257.8g of crystals Compound. (89.7% yield).

The synthetic route of Methyl 2-oxoindoline-6-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Beijing Kanglisheng Pharmaceutical Development Co., Ltd.; Cheng Gang; (12 pag.)CN104844499; (2017); B;,
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. 7699-18-5, name is 5-Methoxyindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

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 7699-18-5 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 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. 21857-45-4, name is 5-Methoxyindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Methoxyindoline

12 g of compound obtained in the preceding step are heated at 140 C. for 3 h in HBr (48%, 200 ml). After cooling to AT, filtering, the filtrate is concentrated dry. The residue is washed with acetone and dried. 14.8 g of desired product are obtained and used as such.

The synthetic route of 21857-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEREP; US2009/233910; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 99365-40-9, name is 6-Bromoindolin-2-one, 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 99365-40-9, Product Details of 99365-40-9

To a warm, stirred solution of 6-bromo-2-oxindole (4 g, 26.3 mmol) dissolved in 60 mL toluene and 60 mL ethanol was added tetrakis(triphenylphosphine)palladium(0) (2.3 g, 1.9 mmol) followed by 2M aqueous sodium carbonate (50 mL, 100 mmol) and thiophene-2-boronic acid (4.38 g, 34.2 mmol) in three portions over 1.5 hours. The mixture was stirred at 100 C. in an oil bath for 12 hours. The mixture was then diluted with ethyl acetate (400 mL) and washed with saturated sodium bicarbonate (200 mL), water (200 mL) and brine (200 mL). The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated to give 2.53 g (42%) of 6-thiophen-2-yl-1,3-dihydro-indol-2-one a tan solid. 1H NMR (360 MHz, DMSO-d6) delta 10.42 (s, 1H, NH), 7.50 (dd, J=0.83 and 4.97 Hz, 1H, Ar-H), 7.43 (dd, J=0.89 and 3.52 Hz, 1H, Ar-H), 7.21 (s, 2H, Ar-H), 7.10 (dd, J=3.31 and 4.82 Hz, 1H, Ar-H), 7.01 (s, 1H, Ar-H), 3.47 (s, 2H, CH2CO). MS EI: 215 [M]+.

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; Sugen, Inc.; US6689806; (2004); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, 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 118289-55-7, COA of Formula: C10H9Cl2NO

General procedure: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

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:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, molecular formula is C9H7NO3, 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.

Into a 10-mL round-bottom flask was placed 2-oxo-2,3-dihydro-1H-indole-5- carboxylic acid (48 mg, 0.27 mmol, 2.00 equiv), 1-hydroxybenzotrizole (40 mg, 1.26 mmol, 2.00 equiv), triethylamine (50 mg, 0.49 mmol, 4.00 equiv), N-[4-[(2S,4S)-4- amino-2-methylpiperidine-1-sulfonyl]phenyl]acetamide (40 mg, 0.13 mmol, 1.00 equiv), and dichloromethane (4 mL). N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (56 mg, 0.29 mmol, 2.00 equiv) was added batchwise at 0-5oC. The resulting solution was stirred for 16 hours at 25oC. The mixture was then washed with 3×5 mL of brine and the organic layer concentrated under vacuum. The crude product was purified by Prep-HPLC with the following conditions (2-Waters 2767-2(HPLC- 08)): Column, Xbridge Shield RP 18, 5um, 19*150mm; mobile phase, water with 50mmol NH4HCO3and CH3CN (10.0% CH3CN up to 28.0% in 2 min, up to 46.0% in 10 min,up to 100.0% in 1 min, down to 10.0% in 1 min); Detector, UV 254 nm. This resulted in 2.6 mg (4%) of N-[(2S,4S)-1-[(4-acetamidobenzene)sulfonyl]-2- methylpiperidin-4-yl]-2-oxo-2,3-dihydro-1H-indole-5-carboxamide as a white solid

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Epizyme, Inc.; Poley, Megan Allen Clunan; Kunz, Kevin Wayne; Mills, James Edward John; Mitchell, Lona Helen; munckhof, Michael John; Harvey, Darren Martin; (303 pag.)KR2017/45749; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 99365-40-9, name is 6-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H6BrNO

Sodium bis(trimethylsilyl)amide (1.0M in tetrahydrofuran, 9.40 mL, 9.40 mmol) was added dropwise to a stirred suspension of 6-bromoindolin-2-one (preparation 1, 0.40 g, 1.89 mmol) in tetrahydrofuran (4 mL) at -78C. The mixture was stirred for 30 minutes, then 2-chloro-N-(2-chloroethyl)-N-methylethanamine hydrochloride (0.36 g, 1.89 mmol) was added and the mixture was warmed to room temperature. After stirring overnight, water was added to the reaction and the mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4) and evaporated. Purification of the residue by reverse phase chromatography (0% CH3CN in H2O to 100% CH3CN in H2O) gave the title compound as a yellow oil (0.17 g, 31%). LRMS (m/z): 295/297 (M+1)+. 1H-NMR delta (DMSO-d6): 1.68-1.86 (m, 4H), 2.51-2.62 (m, 4H), 2.80-2.87 (s, 3H), 7.00 (s, 1H), 7.14 (d, J=6.0 Hz, 1H), 7.41 (d, J=6.0 Hz, 1H), 8.28 (brs, 1H).

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 99365-40-9.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2108641; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3484-35-3, 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. 3484-35-3 name is 5-Methylindolin-2-one, 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: A reaction mixture of compound 19-21 (2.35 mmol),compound 14-18 (2.14 mmol) and 2 drops of piperidine was stirred at RT for 3 h. The precipitate was filtered off and dried. The crude compound was purified by column chromatography using ethyl acetate in dichloromethane (13%) to afford the desired products (4, 22-32).

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

Reference:
Article; Dai, Hou-Ling; Gao, Li-Xin; Yang, Ying; Li, Jing-Ya; Cheng, Jia-Gao; Li, Jia; Wen, Ren; Peng, Yan-Qing; Zheng, Jian-Bin; Bioorganic and Medicinal Chemistry Letters; vol. 22; 24; (2012); p. 7440 – 7443;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem