Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, 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 32692-19-6, COA of Formula: C8H8N2O2

A suspension of 5-nitroindoline (6) (1.0 g, 6.09 mmol) in toluene (20 mL) was treated with 2-chloroacetyl chloride (0.97 mL, 12.18 mmol) and heated at 110 C for 15 min. ;The reaction was cooled to room temperature, treated with sat. ;NaHCO3 solution and extracted into ethyl acetate. ;The combined organic layer was dried (Na2SO4) and concentrated. ;The crude was purified by flash column chromatography (EtOAc:hexanes, 1:9 to 1:1 then 2 M NH3 MeOH: ;CH2Cl2, 1:9) to obtain the title compound (1.08 g, 74%). ;1H NMR (CDCl3) delta 8.30-8.27 (m, 1H), 8.14 (dd, 1H, J = 2.1, 9.0 Hz), 8.06 (s, 1H), 4.30 (t, 2H, J = 8.7 Hz), 4.18 (s, 2H), 3.33 (t, 2H, J = 8.4 Hz); ESI-MS (m/z, %): 241, 243 (MH+).

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; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107,14;; ; Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-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. Formula: C8H4ClNO2

N-4-methylphenylglycine ethyl ester (0.3 mmol) under air atmosphere,A phthalimide compound (0.2 mmol) and cuprous chloride (0.02 mmol) were placed in a dry reaction tube with stirring magnets.Then, an acetonitrile solvent (2 mL) was added to the test tube, and the reaction tube was reacted in an air atmosphere at 60 C for 24 hours.After the reaction is completed, it is cooled to room temperature, and the solvent is distilled off under reduced pressure using a rotary evaporator.The residue is purified by column chromatography to obtain a pure pale yellow solid 3n.The yield was 67%.

The synthetic route of 5-Chloroisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Donghua University Of Science And Technology; Zhu Zhiqiang; Xiao Lijin; Xie Zongbo; Yue Changgao; (12 pag.)CN108623514; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

Example 343 (BVT074103); 2-anilino-5-[2-(1,3-dihydro-2H-isoindol-2-yl)-2-oxoethyl]-1, 3-thiazol-4 (5H)-one ;(2-anilino-4-oxo-4, 5-dihydro-1, 3-thiazol-5-yl) acetic acid (25 mg, 1 eq) was dissolved in DCM (1 mL) and 1- [3- (dimethylamino) propyl] -3-ethylcarbodiimide hydrochloride (EDC, 29 mg, 1.5 eq), 1-hydroxybenzotriazole hydrate (HOBt, 20 mg, 1.5 eq), and N- methylmorpholine (NMM, 44 u. L, 4 eq) were added sequentially. After 10 min stirring at room temperature isoindoline (13 pL, 1.1 eq) was added and the reaction mixture was stirred overnight at room temperature H,, O (5 mL) and DCM (5 mL) was added, the organic layer separated on a 1-PS syringe and concentrated. Purified by flashtube DCM- MeOH (14: 1). 17 mg, yield 47%. 1H NMR (400 MHz, CHLOROFORM-D) 8 ppm 2.09-2. 45 (m, 2 H), 4.19-4. 42 (m, 1 H), 4.53-4. 77 (m, 4 H), 7.01-7. 22 (m, 7 H), 7.30-7. 42 (m, 2 H). MS [M+H] + m/z = 352.

Statistics shows that Isoindoline is playing an increasingly important role. we look forward to future research findings about 496-12-8.

Reference:
Patent; BIOVITRUM AB; WO2005/75471; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 14192-26-8, A common heterocyclic compound, 14192-26-8, name is Methyl 2-oxoindoline-6-carboxylate, molecular formula is C10H9NO3, 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.

To a stirred solution of methyl 2-oxoindoline-6-carboxylate (10.0 g, 52.33 mmol) in 1,4-dioxane (500 mL) was added selenium dioxide (27.9 g, 261.68 mmol) and the resulting reaction mixture was stirred vigorously at 100 C for 1 h. After completion of the reaction, the reaction mixture was diluted with EtOAc and water and filtered through a bed of celite. The filtrate layers were separated and the organic layer was washed with water and brine, dried over anhydrous Na2S04 and then evaporated under reduced pressure to provide the crude product. This was purified by Comb1-flash using 50% EtOAc in hexanes as eluent to afford methyl 2,3-dioxoindoline-6-carboxylate (3.5 g, 17.06 mmol, 34% yield) as a light yellow solid.

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; CURADEV PHARMA LIMITED; BANERJEE, Monali; MIDDYA, Sandip; BASU, Sourav; YADAV, Dharmendra; GHOSH, Rajib; PRYDE, David; SHRIVASTAVA, Ritesh; SURYA, Arjun; (190 pag.)WO2018/234807; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 13861-75-1, 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. 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

The spiro [cyclopropane-1,3′-indol] -2′-one 63a (3g, 18.8mmol) was dissolved in 3mL of acetonitrile at room temperature was added 2-bromo-1,1-dimethoxyethane ( 3.34g, 19.7mmol), potassium carbonate (12.25g, 37.6mmol), potassium iodide (10mg), the reaction was stirred for 16 hours at room temperature. The reaction solution was concentrated under reduced pressure, the reaction solution was added 100mL of water, extracted with ethyl acetate (100mL × 2), and the combined organic phase was washed with water (100mL × 3), washed with saturated sodium chloride solution (100mL × 2), dried over anhydrous dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. By column chromatography (PE: EtOAc = 4: 1) to give purified 1 ‘- (2,2-dimethoxy-ethyl) spiro [cyclopropane-1,3′-indol] -2′-one 63b (2g, yellow solid), yield: 43.0%.

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, Spiro[cyclopropane-1,3′-indolin]-2’-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing Mingde New Drug Research And Development Co. Ltd; HE, HAI-YING; SHI, WEI-HUA; JIANG, ZHI-GAN; HAN, LI-XIA; SUN, JI-KUI; LI, JIAN; CHEN, SHU-HUI; (175 pag.)TW2016/5834; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 912999-79-2, 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. 912999-79-2, name is 5-Chloroisoindoline hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of Compound 151A (340 mg, 2.36 mmol) and 1-(azidomethyl)-4- methoxybenzene (500 mg, 3.07 mmol) in toluene (15 mL) was stirred at 110 C for 48 hours. The reaction mixture was concentrated and purified by column chromatography on silica gel using ethyl acetate- hexane as eluent to afford a Mixture 151B. LC-MS (ESI) m/z: 278 [M+H]._A Mixture 151B (60 mg, 0.217 mmol) and thionyl chloride (0.45 mL) in methylene chloride (10 mL) was stirred at 50 C for 5 hours. The reaction mixture was concentrated to give isic, which was used directly in the next step without further purification.LC-MS (ESI) m/z: 296 [M+H]._ A Mixture 151C (74 mg, 0.2 17 mmol), 5-chloroisoindoline (38 mg, 0.248 mmol), and K2C03 (60 mg, 0.43 5 mmol) in DMF (6 mL) was stirred at 60 C for 5 hours. The mixture was poured into water (100 mL) and extracted with ethyl acetate (100 mL x 3). The combined extracts were washed with brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with preparative HPLC to afford a Mixture 151D. LCMS (ESI) m/z: 413 [M+H]t

The chemical industry reduces the impact on the environment during synthesis 5-Chloroisoindoline hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 16800-68-3, name is 1-Acetylindolin-3-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 16800-68-3, Formula: C10H9NO2

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

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, 1-Acetylindolin-3-one, other downstream synthetic routes, hurry up and to see.

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

These common heterocyclic compound, 6344-05-4, name is 4-Chloroisatin, 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. Application In Synthesis of 4-Chloroisatin

EXAMPLE 32 7-Chloroindolo[2,1-b]quinazoline-6,12-dione STR40 Using the procedure in Example 12 and substituting isatoic anhydride for 5-chloroisatoic anhydride and 4-chloroisatin for 5-fluoroisatin gave the title compound in 16percent yield: mp 294°-295.7° C.; 1 H NMR (300 MHz, DMSO-d6) delta 8.49(d, 1H) 8.33 (d, 1H) 7.97 (d, 2H) 7.81-7.90 (m, 1H) 7.72-7.80 (m, 1H) 7.52 (d, 1H); MS (M+H)+ 283.

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

Reference:
Patent; PathoGenesis Corporation; US5441955; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 317-20-4,Some common heterocyclic compound, 317-20-4, name is 7-Fluoroisatin, molecular formula is C8H4FNO2, 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: 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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoroisatin, its application will become more common.

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

Adding a certain compound to certain chemical reactions, such as: 16800-68-3, name is 1-Acetylindolin-3-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 16800-68-3, SDS of cas: 16800-68-3

3 -phenylpropionne acid 4 – nitrophenyl-unitz (80.1 mg 0.3 mmol), was obtained. N- Acetylindole -3 -unitz 26.3 mg (0.15 mmol), the carbene-unitz (0.015 mmol), 3.96 mg, 1 diazabicycloundecene 8 – (-7 -) and methylene-methylene chloride shown in Formula 45 mul IV 0.3 mmol were placed in 3 ml a 25 ml unitunito-two-port 2h bottle, and reacted 30 C, under unituniteous conditions, and concentrated, under inert atmosphere protection, unitant-like conditions. The eluate fractions of all the products 10:1 detected were collected by chromatography with petroleum ether: ethyl acetate in the timetime as eluent column chromatography, and the solvent was evaporated to obtain the residue unit, 43 mg and gave rise 95% to unit_.

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:
Patent; China Pharmaceutical University; Du Ding; Sun Kewen; (10 pag.)CN110156800; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem