Month: January 2021

Electric Literature of 132898-96-5,Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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 solution of the N-Boc-protected pyrrolidine (1.0 mmol) in dry DCM (3 mL) at 0 C under argon atmosphere, TFA (1.14 g, 10.0 mmol) was added dropwise. The obtained solution was stirred at 0 C for 30 min followed by stirring at r.t. for 2 h. Subsequently, the solution was poured to cold 10% aq. NaOH (15 mL) and extracted with DCM (3 ¡Á 15 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure resulting in the corresponding unprotected pyrrolidine, which was used in the next step without further purification. The free pyrrolidine (ca. 1 mmol) from the previous step was then taken up in CHCl3 (2.2 mL) and DIPEA (2.0 mmol) was added. The solution was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.5 mmol) in CHCl3/THF (1:1, 15 mL) at room temperature. The resulting mixture was stirred further for 1 h and the solvent was removed under reduced pressure. After purification by flash column chromatography the target isatin sulfonamide was obtained.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Dioxoindoline-5-sulfonyl chloride, its application will become more common.

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 1337533-31-9, 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. 1337533-31-9, name is tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of terr-butyl 5-bromo-4-fluoroindoline-l-carboxylate (2.0 g, 6.33 mmol), 1- methyl-4-(4,4,5,5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- IH-pyrazole (2.0 g, 9.49 mmol) and Na2CO3 (2.0g. 18.98 mmol) in dioxane / 1-120 (27 mL, 3: 1) was added [1,V-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (461 mg, 0.63 mmol). The mixture room temperature, the mixture was concentrated in vacuo. The crude residue was purified bysilica gel chromatography (petroleum ether EtOAc 1: 1) to give the title compound (1.5 g, 75%) as a brown solid.

The synthetic route of tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; ROMERO, F. Anthony; MAGNUSON, Steven; PASTOR, Richard; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy; CRAWFORD, Terry; ALBRECHT, Brian, K.; COTE, Alexandre; TAYLOR, Alexander, M.; LAI, Kwong Wah; CHEN, Kevin, X.; BRONNER, Sarah; ADLER, Marc; EGEN, Jackson; LIAO, Jiangpeng; WANG, Fei; CYR, Patrick; ZHU, Bing-Yan; KAUDER, Steven; (0 pag.)WO2016/86200; (2016); 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 16800-68-3 as follows. Recommanded Product: 1-Acetylindolin-3-one

General procedure: 1a (35.0 mg, 0.2 mmol, 1 equiv.), tert-BuOK (22.4 mg, 0.2 mmol, 1.0 equiv.) were added to a Schlenk tube. Then 2 ml THF was added using a syringe. The reaction mixture was stirred 15min,and then added iodonium salt 2 (0.2 mmol, 1.0 eq). The reaction was stirred at 30C for 10 hours.After cooling to room temperature, the solvent was removed in vacuo and the residue was purifiedby silica gel using a proper eluent (EtOAc/Hexane) to afford the desired products

According to the analysis of related databases, 16800-68-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Yanxia; Han, Jianwei; Liu, Zhen-Jiang; Synlett; vol. 26; 18; (2015); p. 2593 – 2597;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1504-06-9, These common heterocyclic compound, 1504-06-9, name is 3-Methyloxindole, 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.

Step 2: 3-methyl-3-(pyrimidin-5-ylmethyl)-l ,3-dihydro-2H-indol-2-onePyrimidin-5-ylmethanol (510 mg, 4.63 mmol) in tetrahydrofuran (8 mL) at room temperature was treated with sodium hydride (185 mg, 4.63 mmol) and stirred for 5 minutes, sodium salt precipates out of solution. p-Toluenesulfonyl chloride (883 mg, 4.63 mmol) was added and the mixture stirred for one hour, to form pyrimidin-5-ylmethyl 4-methylbenzenesulfonate. In a separate flask 3-methyloxindole (682 mg, 4.63 mmol) and A^V-dimethylethylenediamine (1.538 mL, 10.19 mmol) in tetrahydrofuran (16 mL) were cooled to -78 0C and treated dropwise with n-butyllithium (2.5M in hexanes, 4.08 mL, 10.19 mmol). The mixture was allowed to warm to O0Cand stirred for 15 minutes. The mixture was recooled to -78 0C. To this mixture, the tetrahydrofuran solution of pyrimidin-5-ylmethyl 4-methylbenzenesulfonate was added via cannula and the mixture was allowed to warm to room temperature and stirred for 18 hours. Water (50 mL) was added and the mixture was extracted with ethyl acetate (2 x 50 mL). The combined organic fractions were dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel Biotage 25S, eluting with 0-100% ethyl acetate/isohexane to afford 3-methyl-3-(pyrimidin-5-ylmethyl)-l,3- dihydro-2H-indol-2-one as a white solid.1H NMR (CDCl3): delta 8.97 (s, 1 H), 8.29 (s, 2 H), 7.88 (br s, 1 H), 7.25(d, 1 H, J=7.3 Hz), 7.20 (m, IH), 7.11 (m, 1 H)5 6.74 (d, 1 H, J=7.8 Hz), 3.20 (d, 1 H, J=13.5 Hz), 3.0 (d, 1 H, J=13.5 Hz), 1.57 (s, 3H) MS: m/e 240.19 (M + H)+

The synthetic route of 1504-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2009/45381; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 32692-19-6, 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. 32692-19-6, name is 5-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of 5-nitro-2,3-dihydro-lH-mdole (1.0 g, 6.1 mM) in DMF is treated with CsCO3 (3.0 g, 9.1 mM) and 2-Chloro-N,N-diethyl-acetamide (1.1 g, 7.3 mM) and heated to 8O0C for 16 hours. The solution Is cooled, poured into water, extracted with EtOAc, the organic layer separated, dried (MgSO4) and the solvent removed at reduced pressure. The residue is recrystallized from EtOH. This solid is suspended in EtOH, treated with 10% Pd/C (0.2 g) and the reaction hydrogenated on a Parr Shaker at 50 psi for 2 hours. The reaction is then filtered and the solvent removed at reduced pressure to give the product as a gray solid (0.8 g, 13%). LC/MS 0.46 min. 249 (M+H, 100%); IH-NMR (300 MHz, DMSO-d6) delta 6.56 (m, IH), 6.51 (m, IH), 6.45 (s, IH), 3.80 (bs, 2H)5 3.62 (s, 2H), 3.30 (m, 2H), 3.26 (m, 4H), 2.91 (m, 2H), 1.21 (s, 3H), 1.20 (s, 3H).

The synthetic route of 5-Nitroindoline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2007/97697; (2007); 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. 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H9NO3

Method 2; 6-Methoxycarbonyl-2-oxindole (10 g; 0,052 mol) is suspended in n-butyl acetate (25 ml) at room temperature. To this suspension a solution of chloroacetic anhydride (12,8 g; 0,037 mol) in n-butyl acetate (25 ml) is added within 3 min. The mixture is heated to reflux for 2 h, then cooled to 85 0C and methyl cyclohexane (20 ml) is added. The resulting suspension is further cooled down to room temperature and stirred for 2 h. The mother liquor is separated and the solid is washed with methanol (400 ml) at ambient temperature. The crystals are dried to afford 12,7 g (91 ,5 %) of the “chlohmide” compound as a slightly yellow solid.

According to the analysis of related databases, 14192-26-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/71523; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 60434-13-1, These common heterocyclic compound, 60434-13-1, name is 5-Chloro-1-methylindoline-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: To a mixture of ethyl acetoacetate or methyl acetoacetate (1 eqv), formaldehyde (1.1 eqv) and NH4OAc (1.5 eqv) in acetic acid (3 mL) was added FeWO4 (20 mol%) at room temperature and the mixture was heated at 80 C for 2 h (monitoring by TLC) to give poly-substituted pyridine (3), to this solution isatin (1 eqv) was added and heating continued at same temperature for 3 h (monitoring by TLC). After that the reaction mixture was cooled to room temperature neutralized with sodium bicarbonate and extracted with EtOAc (2 ¡Á 10 mL). The organic layers were washed with brine, dried using sodium sulphate .Evaporation of the solvent gave the crude product which was purified by silica gel column chromatography. Elution of the column with petroleum ether-EtOAc gave the desired product.

The synthetic route of 60434-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Paplal, Banoth; Nagaraju, Sakkani; Sathish, Kota; Kashinath, Dhurke; Catalysis Communications; vol. 103; (2018); p. 110 – 115;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 675109-26-9, name is 6-Bromoisoindolin-1-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 675109-26-9, SDS of cas: 675109-26-9

Preparation 48: 6-bromo-2-[2-(morpholin-4-yl)ethyl]-2,3-dihydro-1 H-isoindol-1 -one (1544) (1545) Sodium hydride (60% dispersion in mineral oil, 34 mg, 1.40 mmol) was added to a suspension of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (250 mg, 1.18 mmol) in DMF (5 mL) and the mixture was stirred for 5 min after hydrogen gas evolution ceased. 4-(2-bromoethyl)morpholine (0.18 mL, 1.3 mmol) was added to the resulting brown solution and the mixture was stirred at RT for 18 h. The mixture was diluted with ethyl acetate and transferred into a separating funnel. Water was added and the crude product was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgS04) and concentrated under vacuum. The residue was triturated with a mixture of diethyl ether and iso-hexane and the resulting precipitate was filtered, washed with iso-hexane and dried under suction to afford the title compond (196 mg, 50%) as a pale yellow solid. LC-MS: [M+H]+ = 325/327.

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-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); 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. 1504-06-9, name is 3-Methyloxindole, A new synthetic method of this compound is introduced below., Application In Synthesis of 3-Methyloxindole

General procedure: Oxindole (0.5 mmol), sulfonyl chloride (0.6 mmol), PPh3 (1.0 mmol), n-Bu4NI (0.1 mmol) and dry1,4-dioxane (0.5 mL) were mixed in an oven dried sealed tube. The mixture was stirred at 80 C for12 h. Then, the solvent was evaporated under reduced pressure and the residue was purified by silicagel column chromatography (PE:EA = 5:1 or PE:EA = 3:1) to afford the pure product.

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; Zhao, Xia; Wei, Aoqi; Lu, Xiaoyu; Lu, Kui; Molecules; vol. 22; 8; (2017);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 341988-36-1,Some common heterocyclic compound, 341988-36-1, name is Methyl indoline-6-carboxylate, molecular formula is C10H11NO2, 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.

Reference Example 7 1-(2-Bromoethyl)-6-methoxycarbonylindoline To 1,2-dibromoethane (15.7 ml) were added 6-methoxycarbonylindoline (2.41 g) and triethylamine (7.8 ml), and the mixture was stirred at 90¡ã C. for 2 hr. Ethyl acetate (150 ml) was added to the reaction mixture, and the mixture was washed with saturated brine (300 ml) and dried over Na2SO4. Ethyl acetate was evaporated under reduced pressure. The obtained residue was purified by column chromatography to give the title compound (1.71 g). IR v(neat) cm-1; 1713, 1611, 1499.

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

Reference:
Patent; Matsui, Hiroshi; Kobayashi, Hideo; Azukizawa, Satoru; Kasai, Masayasu; Yoshimi, Akihisa; Shirahase, Hiroaki; US2003/27836; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem