Tag: M.W=200-300

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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Bromoethoxy)isoindoline-1,3-dione

To a solution of 2-(2-bromoethoxy) isoindoline-l,3-dione (10 g, 37 mmol) and tert-buty 2-(lH-tetrazol-5-yl)ethylcarbamate (7.88 g, 37 mmol) in dimethyl formamide (50 ml) was added cesium carbonate ((14.48 g, 44 mmole) in portion wise at 25-30 C under stirring. The reaction mixture was stirred for further 16 hours and filtered; the filtrate was slowly poured into chilled water (400 ml) under stirring and continued stirring for 30 minutes. The formed precipitates of compound were filtered and washed with water (40 ml). The solid compound was dried at 40C for 2 hour under high vacuum, yielded 12 g. The compound was column purified using hexane and acetone as an eluent. The mixture was isolated at 10-15% concentration of acetone in hexane to yield 10 g of 2-{2-[5-(2-tertiary butoxy carbonyl aminoethyl)-2H-tetrazol-2-yl]ethoxy}-lH-isoindole-l,3(2H)-dione and 2-{2-[5-(2-tertiary butoxy carbonyl aminoethyl)-lH-tetrazol-l-yl]ethoxy}-lH-isoindole-l,3(2H)-dione in 67% yield. Analysis: Mass: 403 (M+l); for Molecular weight: 402 and Molecular formula: C18H22N6O5.

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; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, 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 132898-96-5, category: indolines-derivatives

T he hydrochloride salt of 3,3-difluoropyrrolidine (475 mg, 3,3 mmol) ^as added to a solution of2.3-dioxoiotando.me-5-suifonyl chloride (1 ,0 g, 4, 1 mmol) and diisopropyleth) 1 amine (2 0 ml, 12 mmol) in 1 : 1 CH2Cl2ZTHF (40 mL) at -50 C. The solution was warmed to room temperature and stirred at that temperature for 12 hours The reaction mixture was then concentrated, dissolved in CH2Cl2. and washed with saturated NaHCOj and brine. The organic layer was dried (MgSO4), filtered, concentrated, and purified by flash chromatography on silica gel (5% MeOH in CH2Cl2) to provide 575 mg of the product as an orange solid

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, 2,3-Dioxoindoline-5-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH LLC (FORMERLY KNOWN AS WYETH); DOLLINGS, Paul, Jeffrey; DONNELL, Andrew, Forrest; GILBERT, Adam, Matthew; ZHANG, Minsheng; HARRISON, Boyd, Lynn; STANTON III, Charles, John; O’NEIL, Steven, Victor; HAVRAN, Lisa, Marie; CHONG, Dan, Chaekoo; WO2010/77839; (2010); A1;,
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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 118289-55-7 as follows. COA of Formula: C10H9Cl2NO

Example 1 6-chloro-5-(2-(4-(2,3-dihydrobenzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)indolin-2-one 6-chloro-5-(2-chloroethyl)indolin-2-one (120 mg, 0.52 mmol), the product of Reference Example 12 (115 mg, 0.52 mmol), potassium carbonate (215 mg, 1.56 mmol), potassium iodide (86 mg, 0.52 mmol) and acetonitrile (5 ml) were added to the flask and the mixture was stirred at 85 C. overnight. The reaction mixture was concentrated and subjected to column chromatography to obtain a white solid (120 mg, yield: 56%). 1HNMR (300 MHz, DMSO-d6): delta ppm 10.42 (brs, 1H), 7.21 (s, 1H), 7.07 (t, 1H), 6.90 (d, 1H), 6.80 (s, 1H), 6.69 (d, 1H), 3.45 (s, 2H), 3.30 (t, 2H), 3.14 (t, 2H), 2.74-2.95 (m, 6H), 2.59 (brs, 4H), 2.50 (t, 2H). ESI-MS (m/z): 414.2 [M+H]+.

According to the analysis of related databases, 118289-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES; SUZHOU VIGONVITA LIFE SCIENCES CO., LTD.; TOPHARMAN SHANDONG CO., LTD.; JIANG, Hualiang; WANG, Zhen; LI, Jianfeng; ZHANG, Rongxia; HE, Yang; LIU, Yongjian; BI, Minghao; LIU, Zheng; TIAN, Guanghui; CHEN, Weiming; YANG, Feipu; WU, Chunhui; WANG, Yu; JIANG, Xiangrui; YIN, Jingjing; WANG, Guan; SHEN, Jingshan; (70 pag.)US2017/158680; (2017); A1;,
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Some common heterocyclic compound, 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-dione, molecular formula is C16H13NO2, 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. Product Details of 101207-45-8

REFERENTIAL EXAMPLE 11 To 50.3 g of 4-phthalimidomethyltoluene, were added 39 g of N-bromosuccinimide (NBS), 1.5 g of benzoyl peroxide (BPO), and 500 ml of carbon tetrachloride. The mixture was heated under reflux for one hour. The reaction mixture was cooled in ice, filtered from insolubles, and concentrated under reduced pressure. The residue was recrystallized from methanol to yield 40 g of colorless needle crystals of 4-phthalimidomethylbenzyl bromide; m.p. 129-131 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 101207-45-8, its application will become more common.

Reference:
Patent; Torii & Co. Ltd.; US4598077; (1986); A;,
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Indoline | C8H9N – PubChem

20780-72-7, name is 4-Bromoisatin, 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 4-Bromoisatin

General procedure: At first, 0.5mmol of aryl aldehyde or isatin was added to a mixture of ketone (cyclohexanone or acetone, 5equiv), 15 or 20molpercent catalyst, 30 or 40molpercent acid, and 2.0mL of solvent at reaction temperature. The reaction mixture was stirred for the indicated time and then purified through flash column chromatography on a silica gel (petroleum ether/ethyl acetate) to afford the pure products.

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

Reference:
Article; Xu, Biao; Li, Lei; Gou, Shaohua; Tetrahedron Asymmetry; vol. 24; 24; (2013); p. 1556 – 1561;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6326-79-0, A common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, molecular formula is C8H4BrNO2, 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: Isatins (1a-j, 3.0 g), hydrazine hydrate (80%, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L-1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a-j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.

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; Zhang, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20870-90-0, 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. 20870-90-0 name is 5-Bromo-1-methyl-2-oxoindoline, 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.

11. Preparation of I -methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)indolin-2-one 5-Bromo-1-methylindolin-2-one (537 mg, 2.375 mmol),bis(pmnacolate)diborane (987 mg, 3.89 mmol), potassium acetate (636mg, 6.48 mmol) and Pd(dppf)C12.CH2CI2 (88 mg, 0.108 mmol) wereloaded in a microwave vial and DME (15.6 ml) was added. The reaction mixture was heated at 80 C overnight and was then concentrated. The crude was purified by chromatography on silica gel (biotage, CyHex/EtOAc) to give the product(500 mg, 85%). 1H-NMR (500 MHz, CDCI3) ppm = 7.78 (d, J=7.7, IH), 7.69 (s, IH), 6.84 (d, J7.7, IH), 3.52 (s, 2H), 3.24 (s, 3H), 1.36 (s, 12H). LC – MS (ESI, m/z) Rt = 2.90 mm- 274 (M-?-H) (HPLC method E).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methyl-2-oxoindoline, and friends who are interested can also refer to it.

Reference:
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LIMITED; SCHIEMANN, Kai; STIEBER, Frank; CALDERINI, Michel; BLAGG, Julian; MALLINGER, Aurelie; WAALBOER, Dennis; RINK, Christian; CRUMPLER, Simon Ross; (127 pag.)WO2015/144290; (2015); A1;,
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337536-15-9, name is 4-Bromoisoindolin-1-one, 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 C8H6BrNO

Step 4: Preparation of 4-bromo-7-nitroisoindolin-1-one (5) To a solution of 4-bromoisoindolin-1-one 4 (3.0 g, 14.1 mmol) in conc. H2SO4 (6 mL) at 0 C. was added dropwise a solution of conc. HNO3 (1 mL) in conc. H2SO4 (6 mL) The resulting mixture was then stirred at room temperature overnight, then poured over ice, and filtered. The filter cake was washed with water, MTBE, dried in vacuo to give the title product 5 (3.0 g). 1H NMR (400 MHz, DMSO-d6) delta 9.17 (s, 1H), 8.06-8.04 (d, J=8.4 Hz, 1H), 7.89-7.87 (d, J=8.4 Hz, 1H), 4.39 (s, 2H).

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GREEN CROSS CORPORATION; CHOI, Soongyu; PARK, Eun-Jung; SEO, Hee Jeong; KONG, Younggyu; SON, Ickhwan; MA, Sang-ho; CHA, Man-Young; KIM, Mi-Soon; PARK, Kisoo; (143 pag.)US2016/311772; (2016); 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. 885272-46-8, name is tert-Butyl 4-bromoindoline-1-carboxylate, A new synthetic method of this compound is introduced below., SDS of cas: 885272-46-8

A solution of tert-butyl 4-bromoindoline-1-carboxylate (0.50g),bis(triphenylphosphine)palladium(II) dichioride (0.24 g), copper iodide (64 mg),triphenyiphosphine (0.18 g), hexamethyldisilazane (0.52 mL) and triethylamine (1.7 g) in DMF (8.4 mL) was evacuated and backfilied with nitrogen three times. The mixture was stirred for 10 minutes at 110 C. 2-[2-(4-Ethynylphenoxy)ethoxyjtetrahydropyran (0.83 g) was added into the mixture. The reaction mixture was stirred for 5 hours at 110 C and overnight at room temperature, quenched with water and extracted with EtOAc. The organiclayer was washed with water twice, dried over MgSO4, filtered and concentrated in vacuo. The residue was charged onto ISOLUTE HM-N and purified with OH-type silica gel column chromatography (3-100 % EtOAc in n-hexane) to give the title compound (0.57 g, 73 % yield) as a colorless solid.?H NMR (600 MHz, CHLOROFORM-d)6 ppm 1.50- 1.67(m, 13 H), 1.71 – 1.79(m, I H),1.81 – 1.89 (m, I H), 3.18 -3.25 (m, 2 H), 3.51 -3.57 (m,1H), 3.80-3.86 (m, I H), 3.87-3.93 (m, 1 H), 3.96 – 4.10 (m, 3 H), 4.13 – 4.23 (m, 2 H), 4.68 – 4.74 (m, 1 H), 6.89 – 6.94 (m,2 H), 7.05 – 7.17 (m, 2 H), 7.26 – 7.27 (m, 1 H), 7.40 – 7.48 (m, 2 H).

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; TAISHO PHARMACEUTICAL CO., LTD.; TAKASHIMA, Hajime; USHIYAMA, Fumihito; YAMADA, Yousuke; MATSUDA, Yohei; YOSHIZUMI, Takashi; KIM, Chunhae; YAMAGISHI, Junya; ARRATE, Alba Teresa Macias; ROUGHLEY, Stephen David; McKENNA, Sean; WALMSLEY, David Lee; (108 pag.)WO2018/216823; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 200049-46-3, 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 200049-46-3 as follows.

[00259] A stirred mixture of Int-A (200 mg, 0.984 mmol), 7-bromoisoindolin-l-one 1 (240 mg, 1.13 mmol), XPhos (47 mg, 0.098 mmol), Cs2C03 (800 mg, 2.46 mmol), and fert-butanol (7.8 mL) at rt, was purged with a stream of argon for 5 min. Pd2(dba)3 (90 mg, 0.098 mmol) was added and the vial was sealed and heated at 100 C for 16 h. The mixture was cooled to rt and concentrated under reduced pressure. The residue was partitioned between DCM and water. The organic layer was separated and the aq layer re-extracted with additional DCM. The combined organic layers were dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified via reverse-phase preparative HPLC (X-Select CSH C18 250 chi 19 mm, 5mupiiota column; eluting with 10-90% MeCN/H20 containing 0.05% TFA, over 30 min) to afford compound 2 (52 mg, 12%) as a yellow solid. LCMS Mass: 335.0 (M++l).

According to the analysis of related databases, 200049-46-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIDECAR THERAPEUTICS, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John. H.; (178 pag.)WO2019/70742; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem