Tag: M.W=100-200

39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, 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. Computed Properties of C10H9NO2

General procedure: Isatin 1 (3 mmol), 0.198 g malononitrile (3 mmol),0.420 g dimedone (3 mmol), and 0.025 g sodium acetate(0.3 mmol) were grinded with the pestle in mortar atambient temperature for 15 min. The resulting mixture wasair dried. Crude solid was then put on filter, rinsed withwater (2 9 2 cm3), and dried with water pump.

The synthetic route of 39603-24-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Elinson, Michail N.; Ryzhkov, Fedor V.; Zaimovskaya, Tatiana A.; Egorov, Mikhail P.; Monatshefte fur Chemie; vol. 147; 4; (2016); p. 755 – 760;,
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. 20876-36-2, name is 5-Aminoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 5-Aminoindolin-2-one

Preparation of 5-(4-Chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-1,3-dihydro-indol-2-one (4) To a solution of 5-trifluoromethyl-2,4-dichloropyrimidine (214.8 g; 0.921 mol) in 1:1 DCE/tBuOH (1.240 L) was added Zinc chloride 1M solution in ether (1 eq; 0.921 L). After 0.5 hour, 5-amino-oxindole (124 g; 0.837 mol) was added followed by triethylamine (129.4 ml; 0.921 mol) keeping temperature at 25° C. The reaction was allowed to stir at room temperature overnight, then was concentrated and the product triturated from methanol as a yellow solid (224.3 g; 82percent). 1H NMR (DMSO-d6, 400 MHz) .box. 3.29 (s, 2H), 6.76 (d, J=7.9 Hz, 2H), 7.39 (d, J=8.3 Hz), 7.51 (br s, 1H), 8.71 (s, 1H), 10.33 (s, 1H), 10.49 (s, 1H), 13C NMR (DMSO-d6, 100 MHz) .box. 177.0, 161.3, 158.7 (br), 140.7, 132.8, 126.9, 123.7 (q, J=268 Hz), 121.0, 118.7, 111.2 (q, J=32 Hz), 109.6, 36.7; HPLC ret. time: 5.759 min. LRMS (M+) 329.1, 331.1.

The synthetic route of 20876-36-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc; US2005/256145; (2005); A1;,
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Indoline | C8H9N – PubChem

Related Products of 59-48-3, 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. 59-48-3 name is Indolin-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.

A stirred mixture of sodium hydride (60%, 31g, 0.79 mol) in dry xylene (500 mL), under a nitrogen atmosphere, was heated to reflux for 30 min. l,3-Dihydro-indol-2-one 16a (100 g, 0.75 mol) was then slowly added via an addition funnel and stirred at reflux for 1.5 hrs. Dimethyl sulfate (104 g, 0.83 mol) was added drop-wise, whereupon the resulting homogeneous solution was refluxed for an additional 2 hrs. After cooling to room temperature, the reaction mixture was washed with water, dried over Na2SC>4, and concentrated under reduced pressure to afford l-methyl-l,3-dihydro-indol-2-one 16b (74 g, 67.3%). .HNMR (300 MHz, CDC13) 5 7.23-7.31 (m, 2 H), 7.04 (t, J= 7.5 Hz, 1 H), 6.82 (d, J= 7.8 Hz, 1 H), 3.52 (s, 2 H), 3.21 (s, 3 H).[0270] A suspension of NaH (60%, 70 g, 0.48 mol) in THF (300 mL) was stirred for 10 min at 0 C. Then a solution of l-methyl-l,3-dihydro-indol-2-one 16b (70 g, 2.88 mol) in THF (200 mL) was added at 0 C, and the mixture was stirred for 1 h at room temperature. Benzyl-bis-(2-chloro-ethyl)-amine (129 g, 0.48 mol) was added in portions at 0 C. The mixture was stirred overnight at room temperature, and then was poured into ice-water, extracted with EtOAc. The combined organic layers were dried over IS^SO^ and concentrated under reduced pressure. The residue was purified by column on silica gel (P.E./E.A. 2:1) to give compound 16c (24 g, 16.3%). lH NMR (300 MHz, CDCI3) 5 7.25-7.42 (m, 7 H), 7.02-7.07 (m, 1 H), 6.83 (d, J= 7.5, 1 H), 3.68 (s, 2 H), 3.19 (s, 3 H), 2.74-2.99 (m, 2 H), 2.66-2.72 (m, 2 H), 1.93-2.01 (m, 2 H), 1.79-1.85 (m, 2 H).[0271] To a solution of compound 16c (12 g, 39.2 mmol) in MeOH (100 mL) was added Pd(OH)2/C (1.5 g, 20%>) under N2. The suspension was hydrogenated under H2 (50 psi) at room temperature for 4.5 hrs. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give the deprotected spiroindolone product 16d (8 g, 94.5%). ]H NMR (400 MHz, DMSO-rf6) 5 7.46 (d, J= 7.2,1 H), 7.23-7.27 (m, 1 H), 6.96-7.03 (m, 2 H), 3.04-3.14 (m, 5 H), 2.83-2.89 (m, 2 H), 1.61-1.67 (m, 2 H), 1.45-1.51 (m, 2 H). MS (ESI) m/z 217.1 [M+H]+ [0272] 1.0 eq of deprotected spiroindolone 16d (22 mg, 0.10 mmol) was dissolved in anhydrous l,2-dichloroethane:l,2-dimethoxyethane (1.0 mL, 1:1 v/v) and treated with 1.5 N-Carbethoxy-4-tropinone (30 mg, 0.15 mmol), followed by titanium tetraisopropoxide (88 /xL, 85 mg, 0.30mmol). The vial was flushed with nitrogen and stirred at room temperature ~70 h. The reactionwas then diluted with methanol (1.0 mL), cooled in an ice-BbO bath and treated with sodiumborohydride (8 mg, 0.20 mmol). After warming to room temperature and stirring for 90 min, thereaction was further diluted with methanol (2.0 mL), quenched with 1.0 N NaOH (500 juL) andstirred vigorously at room temperature for 10 min. The suspension obtained was centrifuged(3K rpm, 10 min) and the supernatant concentrated under reduced pressure. The residueobtained was dissolved in MeOH:acetonitrile (1250 fiL, 1:1 v/v), filtered, and purified byreverse-phase HPLC (2-40% CH3CN/0.1% TFA gradient over 10 min) to yield productcompound no. 149. LC/MS (10-99%) m/z [M+H]+398.2, retention time 1.93 min.

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

Reference:
Patent; VERTEX PHARMACEUTICALS, INCORPORATED; WO2006/23852; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 13220-46-7, 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. 13220-46-7, name is 4-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

4-Methyl-oxindole was condensed with 3-(2-formyl-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrol-3-yl)-propionic acid and piperidine in ethanol to give the title compound. MS (m/z) 365 [M+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, 4-Methylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUGEN, Inc.; US2004/186160; (2004); A1;,
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. 56341-39-0, name is 6-Fluoroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6FNO

PREPARATION 3 1-(3-Chloropropionyl)-6-fluoroindoline This provides an alternative method of preparing the title compound, whose preparation is also described in Example 1(6). 424 ml (3.35 mol) of a boron trifluoride-diethyl ether complex were added dropwise at 0 C. over a period of 40 minutes to 1.5 liters of a suspension of 106 g (2.52 mol) of sodium borohydride (purity 90%) in tetrahydrofuran, and the mixture was stirred at room temperature for 1 hour. At the end of this time, 194 g (1.28 mol) of 6-fluorooxindole was added at 0 C. to the reaction mixture, and the mixture was heated under reflux for 84 hours. The reaction mixture was then cooled to 0 C., after which 1 liter of 6N aqueous hydrochloric acid was added dropwise over a period of 30 minutes. The resulting mixture was heated under reflux for 2 hours, after which it was concentrated by distillation at atmospheric pressure until the volume of the reaction mixture was reduced to about 1 liter. About 400 g of sodium hydroxide was added to the reaction mixture at 0 C. over a period of 1 hour to adjust the pH to a value of at least 14, and then the mixture was filtered. The filtrate was extracted with 1 liter of ethyl acetate and the organic extract was dried over anhydrous sodium sulfate. The mixture was filtered, and then the solvent was removed from the filtrate by distillation under reduced pressure to obtain 370 g of a crude product containing 6-fluoroindoline. This crude product was dissolved in 1 liter of acetone, and 125 ml of 3-chloropropionyl chloride was added dropwise to the resulting solution at 0 C. over a period of 50 minutes, after which the mixture was heated under reflux for 40 minutes. The reaction mixture was then cooled to room temperature and concentrated by evaporation under reduced pressure until the volume of the mixture was reduced to about 400 ml. 500 ml of water and 100 ml of acetone were added to the reaction mixture, and the precipitated crystals were collected by filtration. The crystals were washed with water and then air-dried. The crystals thus obtained were washed with a 2:3 by volume mixture of ethyl acetate and hexane and then with hexane and dried to obtain 158 g (yield: 54%) of the title compound as pale yellow crystals.

According to the analysis of related databases, 56341-39-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sankyo Company, Limited; US5773618; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 16800-68-3,Some common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, 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 10 mL glass tube equipped with a stirring bar was charged with the isatin-derived N-Boc ketimine 1 (0.44 mmol, 1.2 equiv), the N-acetylindolin-3-one 2 (0.4 mmol, 1.0 equiv), catalyst 4o (0.02 mmol, 2 mol%) and CH2Cl2 (4.0 mL). The resulting solution was stirred at r.t. for the indicated time. The solvent was then evaporated to give the crude product, which was directly purified by flash chromatography (n-pentane/EtOAc, 4:1 to 1:1) to provide the desired products 3a-t.

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gajulapalli, V. Pratap Reddy; Jafari, Ehsan; Kundu, Dipti S.; Mahajan, Suruchi; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter; Synthesis; vol. 49; 22; (2017); p. 4986 – 4995;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, 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 7477-63-6, Computed Properties of C8H4ClNO2

General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken ina 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, thereaction mixture was allowed to cool, quenched with water (10 mL) and extractedwith DCM (3 x 20 mL). The combined organic extracts were dried over anhydrousNa2SO4, filtered and volatiles were removed in vacuo. Thecrude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 percent ethyl acetate in petroleum ether to afford compound (4).

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; Karmakar, Rajiv; Kayal, Utpal; Bhattacharya, Biswajit; Maiti, Gourhari; Tetrahedron Letters; vol. 55; 7; (2014); p. 1370 – 1372;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 16800-68-3,Some common heterocyclic compound, 16800-68-3, name is 1-Acetylindolin-3-one, molecular formula is C10H9NO2, 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 10 mL glass tube equipped with a stirring bar was charged with the isatin-derived N-Boc ketimine 1 (0.44 mmol, 1.2 equiv), the N-acetylindolin-3-one 2 (0.4 mmol, 1.0 equiv), catalyst 4o (0.02 mmol, 2 mol%) and CH2Cl2 (4.0 mL). The resulting solution was stirred at r.t. for the indicated time. The solvent was then evaporated to give the crude product, which was directly purified by flash chromatography (n-pentane/EtOAc, 4:1 to 1:1) to provide the desired products 3a-t.

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gajulapalli, V. Pratap Reddy; Jafari, Ehsan; Kundu, Dipti S.; Mahajan, Suruchi; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter; Synthesis; vol. 49; 22; (2017); p. 4986 – 4995;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1074-82-4, The chemical industry reduces the impact on the environment during synthesis 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, I believe this compound will play a more active role in future production and life.

[0714] Step 11: Synthesis of 2-(5-bromopentyl) isoindoline-1,3-dione (14-k) To a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 min at room temperature. After complete addition, the reaction mixture was stirred at 90C for 18 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10% EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65% yield). 1H NMR (400 MHz, CDCl3): delta 7.82 (dd, J = 5.5, 3.1Hz, 2H), 7.69 (dd, J = 5.5, 3.0 Hz, 2H), 3.68 (t, J = 7.2 Hz, 2H), 3.38 (t, J = 6.8 Hz, 2H), 1.93-1.85 (m, 2H), 1.70 (p, J = 7.5 Hz, 2H), 1.53-1.43 (m, 2H).

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, Potassium 1,3-dioxoisoindolin-2-ide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; LADNER, Robert D.; (345 pag.)WO2018/128720; (2018); A1;,
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. 13220-46-7, name is 4-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 13220-46-7

5-Chloro-4-methyl-2-oxindole A suspension of 3.0 g of 4-methyl-2-oxindole was stirred in 50 ML of acetonitrile at room temperature while 3.3 g of N-chlorosuccinimide was added in portions.. trifluoroacetic acid (1 ML) was then added.. The suspension was stirred at room temperature for 3 days during which time solid was always present.. The white solid was collected by vacuum filtration, washed with a small amount of cold acetone and dried overnight in a vacuum oven at 40 C. to give 2.5 g (68%) of 5-chloro-4-methyl-2-oxindole.

According to the analysis of related databases, 13220-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem