Month: March 2021

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. 20870-79-5, name is 5-Nitroindolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6N2O3

Example 43 tert-Butyl 3-(5-nitro-2-oxoindolin-3-ylidene)pyrrolidine-1-carboxylate (2) A solution of compound 1 (1.0 g, 5.613 mmol), N-Boc-3-pyrrolidinone (1.039 mL, 5.613 mmol) in 7 N NH3 in methanol (10 mL) was refluxed for 2 h. The reaction was brought to room temperature, filtered, washed with methanol (2*5 mL) and dried under vacuum to obtain compound 2 as a solid (1.88 g, 97%). 1H NMR (DMSO-d6) delta 11.29 (s, 1H), 8.19 (dd, 1H, J=2.1, 8.7 Hz), 8.14 (d, 1H, J=1.8 Hz), 7.05 (d, 1H, J=8.4 Hz), 4.56 (s, 2H), 3.61 (t, 2H, J=7.2 Hz), 3.36-3.30 (m, 2H, merged with DMSO peak), 1.44 (s, 9H); ESI-MS (m/z, %): 368 (M+Na, 23), 272 (48), 246 (MH+-Boc, 100).

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; MADDAFORD, Shawn; RAMNAUTH, Jailall; RAKHIT, Suman; PATMAN, Joanne; ANNEDI, Subhash C.; ANDREWS, John; DOVE, Peter; SILVERMAN, Sarah; Renton, Paul; US2008/234237; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 101207-45-8, These common heterocyclic compound, 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-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.

A mixture of 243 2-(4-methylbenzyl)isoindoline-1,3-dione (1 g, 3.8 mmol) and 24 hydrazine hydrate (752 mg, 15 mmol, 730 muL) in 113 MeOH (10 mL) was stirred at 20 C. for 3 hours. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (dichloromethane:methanol (with 5% 245 ammonia in 55 water)=0:1 to 5:1) to give 246 p-tolylmethanamine (160 mg).

Statistics shows that 2-(4-Methylbenzyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 101207-45-8.

Reference:
Patent; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Kehler, Jan; Rasmussen, Lars Kyhn; Clementson, Carl Martin Sebastian; Marigo, Mauro; (154 pag.)US2019/194189; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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. Computed Properties of C10H7NO2

Using N-vinylphthalimide and diphenylphosphine oxide as raw materials, the reaction steps are as follows:(1) Add N-vinylphthalimide (0.069 g, 0.4 mmol) to the reaction flask, diphenylphosphine oxide (0.081 g, 0.4 mmol),tert-butyl nitrite (0.041 g, 0.4 mmol), silver nitrate (0.07g, 0.04 mmol), ethanol (2.5mL), 30C reaction;(2) TLC tracks the reaction until complete;(3) The crude product obtained after completion of the reaction was separated by column chromatography (ethyl acetate:petroleum ether=1:1) to give the target product (yield 71%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3485-84-5, its application will become more common.

Reference:
Patent; Jiangsu Qiangsheng Function Chemical Co., Ltd.; Zou Jianping; Ying Zhiyao; Zhang Peizhi; Tao Zekun; Li Jianan; (19 pag.)CN107573378; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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 31 (0.300 g, 0.852 mmol) in THF (10 mL) was added isopropylmagnesium chloride (0.46 mL, 2M solution in THF, 0.920 mmol) at room temperature. After 1 h the reaction mixture was cooled to -20 C and a solution of 3-(1,3-dioxoisoindolin-2-yl)propanal (32) (0.144 g,0.709 mmol) in THF (3 mL) added. The resulting solution was warmed to room temperature, quenched with brine (20 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organics were dried (Na2SO4), filtered and concentrated to give 33 which was used without purification in the next step

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACUCELA INC.; WO2008/131368; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 7699-18-5, A common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-one, molecular formula is C9H9NO2, 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: The appropriate compound 2 (10 mmol) was dissolved inmethanol (100 mL) and treated with the equivalent of the appropriatealdehyde 1 and piperidine (1 mL). For compounds 39, 41 and42 the yield was much lower (5%), and an improvement (15-20%)was obtained by replacing piperidine with 33% NH4OHThe reaction mixture was refluxed for 5-10 h, except for compounds39-42 which required a longer reflux time (16-24 h; theprogress of the reaction was followed by TLC). The precipitate,formed on cooling, was collected by filtration.Compounds 39e41 were purified by column chromatographywith petroleum ether/acetone as the eluent. Most of the crudeproducts were crystallized from methanol, except 27 (acetone/petroleumether), 34, 43-48, 50-52 (ethanol) and 42, 49 (toluene). Inthe case of compound 10, the two E/Z isomers were isolated byfractional crystallization from methanol.

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; Morigi, Rita; Locatelli, Alessandra; Leoni, Alberto; Rambaldi, Mirella; Bortolozzi, Roberta; Mattiuzzo, Elena; Ronca, Roberto; Maccarinelli, Federica; Hamel, Ernest; Bai, Ruoli; Brancale, Andrea; Viola, Giampietro; European Journal of Medicinal Chemistry; vol. 166; (2019); p. 514 – 530;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 675109-26-9, A common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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.

6-Bromoisoindolin-1-one (636 mg, 3.10 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (930 mg, 3.70 mmol), and Pd(dppf)Cl2 (125 mg, 0.150 mmol) were added to a dry flask and placed under N2. Potassium acetate (900 mg, 9.20 mmol) was weighed directly into the flask. The flask was then evacuated and back filled with N2. Anhydrous N,N-dimethylformamide (DMF) (18 mL) was added and the reaction was heated at 80 C. overnight. The reaction mixture was evaporated to dryness and the resulting material was purified by silica gel chromatography eluting with 0-100% ethyl acetate in hexane to yield 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (493 mg, 62%). ESI-MS m/z calc. 259.1, found 260.1 (M+1)+. Retention time 1.24 minutes.

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; HADIDA RUAH, SARA S.; Miller, Mark; Zhou, Jinglan; Bear, Brian; Grootenhuis, Peter; US2009/143381; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3484-35-3, A common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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 solution of appropriate oxindole (8a-e, 0.3 mmol) in ethanol (3 mL) was addedcorresponding aldehyde (12a-h, 0.32 mmol) and a catalytic amount of piperidine. The reactionmixture was stirred at reflux for 6-12 h (monitored by TLC). After cooling, the precipitate wasfiltered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(4′-(aminoalkoxy)-3′-methoxybenzylidene)indolin-2-one title compounds of formula (5a-t) as yellow/brown/orangesolids in moderate to excellent yields.

The synthetic route of 3484-35-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Bharghava, Suresh K.; Naidu; Shankaraiah, Nagula; Bioorganic and Medicinal Chemistry Letters; vol. 26; 16; (2016); p. 4061 – 4069;,
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. 912999-79-2, name is 5-Chloroisoindoline hydrochloride, A new synthetic method of this compound is introduced below., SDS of cas: 912999-79-2

General procedure: A mixture of Intermediate J (200 mg, 0.66 mmol), Compound 146A, 3-(4-chlorophenyl)pyrrolidine, (143 mg, 0.79 mmol), HATEG (380 mg, 1 mmol), and DIPEA ( 258 mg, 2 mmol) in DMF (5 mL) was stirred at room temperature overnight. The mixture was diluted with EtOAc (50 mL), washed with brine (15 mL x 3), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified with preparative HPLC give Compound 146B. LC-MS (ESI) m/z: 469 [M +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; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1029691-06-2, 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. 1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation 2; (i?,5′)-2-(7-Bromo-l,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-isoindole-l,3-dione; In a 5 L flask is mixed (i?,5′)-2-(3-oxo-cyclopentyl)-isoindole-l,3-dione (295.3 g, 1.29 mol), 4-bromophenyl hydrazine-HCl (287.9 g, 1.29 mol) and glacial acetic acid (3 L) with mechanical stirring. The reaction is refluxed for 5 h, and then cooled to room temperature. The reaction is poured into water (4 L) with rapid stirring. The solid is collected by vacuum filtration, washed with water (4 L) and air-dried for 30 min. The solid is slurried with MeOH (700 mL), collected by vacuum filtration and rinsed with MeOH (100 mL). The gray solid is air dried for 2 h, then dried overnight in a 50 0C vacuum oven to obtain 414.67 g (84%) of the title compound as a dark solid. ES/MS m/z (7W1Br) 381/383 [M+H]+.

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-Oxocyclopentyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELI LILLY AND COMPANY; WO2009/140448; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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 6941-75-9, name: 5-Bromoisoindoline-1,3-dione

Sodium borohydride (3.48 g, 92.0 mmol) was added to the solutionof 5-bromopthalamide (2.0 g, 8.8 mmol) in THF, and theresultant suspensionwas cooled to 10 C. Then, BF3.Et2O (12.7 mL,102.6 mmol) was added slowly and the reaction mixture wasrefluxed. After 24 h, the reaction mixture was allowed to cool to0 C and cold H2O (18 mL) was added. EtOAc (100 ml) was addedand the reaction mixture was made alkaline using 6.0 M aqueousNaOH. The organic layer was separated and concentrated using arotary evaporator. The residue was diluted with Et2O (50 mL) andacidified to pH 2. The aqueous layerwas separated, made alkaline topH 10 using 6.0 M aqueous NaOH and extracted with EtOAc(70 mL). The organic layer was separated, washed with brine(3 70 mL), dried (Na2SO4) and concentrated using rotary evaporatorto yied the 5-bromo-isoindoline (47). The residue was used infurther reactions without purification.

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; Ojha, Ritu; Nepali, Kunal; Chen, Chun-Han; Chuang, Kuo-Hsiang; Wu, Tung-Yun; Lin, Tony Eight; Hsu, Kai-Cheng; Chao, Min-Wu; Lai, Mei-Jung; Lin, Mei-Hsiang; Huang, Han-Li; Chang, Chao-Di; Pan, Shiow-Lin; Chen, Mei-Chuan; Liou, Jing-Ping; European Journal of Medicinal Chemistry; vol. 190; (2020);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem