Month: July 2021

Synthetic Route of 1254319-51-1, A common heterocyclic compound, 1254319-51-1, name is 6-Bromo-2-methylisoindolin-1-one, molecular formula is C9H8BrNO, 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-Bromo-2-raethylisoindolin-l-one (723 mg, 3.41 mmol), bis(pinacolato)diboron (1.04 g, 4.09 mmol), potassium acetate (1.00 g, 10.2 mmol) and PdCl2(dppf) catalyst (139 mg, 0.17 mmol) were weighed into a flask which was sealed under N2. DMSO (15 mL) was added, and the entire mixture stirred at 90C for 5 h. Upon cooling, the reaction mixture was diluted with water (250 mL) and extracted with CH2C12 (5×50 mL). The combined CH2C12 fractions were in turn washed with water (2×100 mL), brine (100 mL), dried (Na2S04), filtered and the solvent removed under reduced pressure to yield the crude product. Purification was carried out by flash column chromatography on silica gel (20% THF/CH2C12 as eluant) to give the title compound as a crystalline beige solid (262 mg, 28%). NMR [400 MHz, (CD3)2SO] delta 7.91 (br s, 1 H), 7.85 (dd, J = 7.6, 1.0 Hz, 1 H), 7.59 (dd, J = 7.5, 0.6 Hz, 1 H), 4.49 (s, 2 H), 3.07 (s, 3 H), 1.32 (s, 12 H). LRMS (APCI+) calcd for Ci5H2iBN03 274 (MH+), found 274.

The synthetic route of 1254319-51-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PETER MACCALLUM CANCER INSTITUTE; SPICER, Julie Ann; HUTTUNEN, Kristiina Maria; LYONS, Dani Michelle; TRAPANI, Joseph Albert; SMYTH, Mark John; DENNY, William Alexander; WO2011/75784; (2011); A1;,
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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. 86626-38-2, name is 4-Bromoindoline, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Bromoindoline

To a solution of 4-bromoindoline (12.2 g, 61.6 mmol) in dichloromethane (200 mL) was added Boc20 (14.8 g, 67.8 mmol) and DMAP (0.75 g, 6.16 mmol). The mixture was stirred at room temperature for 48 h and then evaporated. The residue was purified by silica gel column chromatography with EtOAc in hexanes (0 to 10% gradient) to provide the title compound (11.5 g, 62.5%). 1H NMR (CDC13) delta: 7.80 (br. s, 1H), 6.98-7.12 (m, 2H), 4.00 (t, J=8.7 Hz, 2H), 3.08 (t, J=8.7 Hz, 2H), 1.50-1.66 (s, 9H).

According to the analysis of related databases, 86626-38-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PTC THERAPEUTICS, INC.; WANG, Jiashi; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; KARP, Gary, Mitchell; QI, Hongyan; WOLL, Matthew, G.; ZHANG, Nanjing; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Maria, L.; (260 pag.)WO2016/25933; (2016); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 56341-37-8, name is 6-Chlorooxindole, 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 56341-37-8, COA of Formula: C8H6ClNO

A solution of 6-chloro-oxindole(184mg, 1.1mmol) in tetrahydrofuran(5ml) and triethylamine(0.3mL) were added to a solution of 3,5-bis(trifluoromethyl)phenylisocyanate(255mg, 1.0mmol) in tetrahydrofuran(5mL) under argon atmosphere, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into diluted hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and brine, and dried over anhydrous magnesium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel(n-hexane:ethyl acetate=4:1) to give the title compound(172.2mg, 40.7%) as a pink solid.1H-NMR(DMSO-d6):delta 3.97(2H, s), 7.29(1H, dd, J=8.1, 2.1Hz), 7.41(1H, d, J=8.1Hz), 7.88(1H, s), 8.04(1H, d, J=2.1Hz), 8.38(2H, s), 10.93(1H, s).

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; Institute of Medicinal Molecular Design, Inc.; EP1535609; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 60434-13-1, 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. 60434-13-1 name is 5-Chloro-1-methylindoline-2,3-dione, 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.

General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Chloro-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Singh, Radhey M.; Bharadwaj, Kishor Chandra; Tiwari, Dharmendra Kumar; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2975 – 2980;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 88150-75-8, The chemical industry reduces the impact on the environment during synthesis 88150-75-8, name is Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, I believe this compound will play a more active role in future production and life.

Stage-1: Preparation of Phthalimido amlodipine:2-chlorobenzaldehyde (27 g) and methyl 3-amino crotonate (64.8 g) are added to the suspension of 4-[2-(Phthalimido) ethoxy] acetoacetate (60 g) in iso-propanol (300 ml). Temperature of the reaction mass is raised and maintained for 21 hrs at reflux temperature. Distilled off the solvent under vacuum at temperature below 75C. Washed the residue with n-Hexane and again removed the low volatiles under vacuum to get residue. Acetic acid (300 ml) is added to the residue, mixed for 22 hrs at room temperature. Crystallized Phthaliimido amlodipine is filtered and washed the wet cake with acetic acid and n-Hexane. The wet cake is again mixed with methanol (150 ml) at room temperature for about 30 min, filtered and dried at 55C – 60C till constant weight.Dry wt of the phthalimido Amlodipine crude is 26 g (Yield: 31.7%).

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, Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MATRIX LABORATORIES LTD; WO2006/3672; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1035235-27-8, These common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, 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 a. To a stirred solution of tert-butyl 4-bromoisoindoline-2-carboxylate (Intermediate 1, 0.2 g, 0.671 mmol) in l,4-dioxane:water (4.1; 5 ml) were added Cs2C03 (0.44 g, 1.342 mmol) and 1-methyl- lH-pyrazole-4-boronic acid pinacol ester (CAS Number 761446-44-0; available from Combi Blocks) (0.17 g, 0.805 mmol) at rt. The reaction mixture was degassed for 20 min. Pd(PPh3)4 (0.077 g, 0.067 mmol) was added to the reaction mixture at rt. The reaction mixture was heated at 85C for 30 min. The resulting reaction mixture was cooled to rt, diluted with water (100 ml) and extracted with EtOAc (3 x 80 ml). The combined organic phase was separated, dried over Na2S04, filtered and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography (30% EtOAc in hexane) yielding tert-butyl 4-(1 -methyl- lH-pyrazol-4-yl)isoindoline-2-carboxylate (0.121 g, 0.404 mmol). LCMS: Method A, 2.335 min, MS: ES+ 300.53; NMR (400 MHz, DMSO-d6) delta ppm 8.03 (d, J=11.2 Hz, 1H), 7.78 (d, J=20.4 Hz, 1H), 7.43 – 7.49 (m, 1H), 7.31 (t, J=7.2 Hz, 1H), 7.19 (t, J=7.6 Hz, 1H), 4.69 (s, 2 H), 4.62 (d, J=11.2 Hz, 2 H), 3.90 (s, 3 H), 1.48 (s, 9 H).

The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 64483-69-8, 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. 64483-69-8, name is 5-Acetylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Ethyl-2-oxindole To 5-Acetyl-2-oxindole (2 g) in 15 mL of trifluoroacetic acid in an ice bath was slowly added 1.8 g of triethylsilane; the reaction was then stirred at room temperature for 5 hours. One mL of triethylsilane was added and the stirring continued overnight. The reaction mixture was poured into ice water and the resulting precipitate collected by vacuum filtration, washed copiously with water and dried under vacuum to give 1.3 g (71% yield) of the title compound as a yellow 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, 5-Acetylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 60434-13-1, 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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: General procedure forthe preparation of oxazolo[5,4-b]quinoline- fused spirooxindoles 4a-t: A reaction of isatin(1 mmol),beta-diketone (1 mmol) and5-amino-3-methylisoxazole (1 mmol) were mixed and irradiated in a closed vesselin the absence of any solvent in a Synthos 3000 microwave reactor at 700 W, 14 bar,and 110 C for 10 min. The reaction was monitored by TLC. Then, thereaction mixture was filtered hot and the resulting solid products were washed with ethanol, dried in air and recrystallized from ethanol.

The chemical industry reduces the impact on the environment during synthesis 5-Chloro-1-methylindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yuvaraj, Panneerselvam; Manivannan, Karthikeyan; Reddy, Boreddy S.R.; Tetrahedron Letters; vol. 56; 1; (2015); p. 78 – 81;,
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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: A mixture of dibromoalkane (23 mmol) and potassium carbonate (12 mmol)was added in acetone (30 mL), and potassium phthalimide (10 mmol) was added slowly over a 15-min period, and then the reaction was heated under reflux for 8-10 h. The reaction mixture was filtered,and the acetone was evaporated in vacuo. The crude product was purified by column chromatography on silica gel using mixtures of petroleum/acetone as eluent) to obtain the white solid compounds 2-4.

The synthetic route of 1074-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pan, Wanli; Hu, Ke; Bai, Ping; Yu, Lintao; Ma, Qinge; Li, Tao; Zhang, Xu; Chen, Changzhong; Peng, Kelin; Liu, Wenmin; Sang, Zhipei; Bioorganic and Medicinal Chemistry Letters; vol. 26; 10; (2016); p. 2539 – 2543;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 172078-33-0,Some common heterocyclic compound, 172078-33-0, name is Indolin-5-ol, molecular formula is C8H9NO, 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 6-(3,5-dimethylisoxazol-4-yl)-7-methoxy-2-oxo-l-(pyri- din-2-ylmethyl)-l,2-dihydroquinoline-3-carbaldehyde (intermediate- le) (0.2 g, 0.51 mmol) in titanium isopropoxide (5 mL) was added indolin-5-ol (0.1 g, 0.77 mmol) followed by stirring at RT for 16 h. After stirring, methanol (20 mL) was added to the mixture at 0 C followed by NaCNBH4 (0.16 g, 2.56 mmol). The mixture was stirred at RT for 2 h. The mixture was then quenched with ammonium hydroxide and the solids were filtered off. The filtrate was extracted with EtOAc (100 mL x 2), washed with water (100 mL) and brine (100 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue was purified to get the title compound as pale brown solid (0.016 g, 6 %). 1H NMR (400 MHz, CDC13) delta 8.60 (d, J=4.8 Hz, 1H), 7.86 (s, 1H), 7.67 (t, J=7.8 Hz, 1H), 7.34 (d, J=7.8 Hz, 1H), 7.27 (s, 1H), 7.23-7.20 (m, 2H), 6.69 (s, 1H), 6.60-6.48 (m, 2H), 5.74 (s, 2H), 4.29 (s, 2H), 3.79 (s, 3H), 3.61-3.59 (m, 2H), 3.10-3.00 (m, 2H), 2.25 (s, 3H), 2.11 (s, 3H); LC-MS: m/z 509.3 (M+H)+.

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

Reference:
Patent; ORION CORPORATION; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; LINNANEN, Tero; WOHLFAHRT, Gerd; (120 pag.)WO2017/1733; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem