Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-2,3-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 324-03-8, Quality Control of 6-Fluoroindoline-2,3-dione

General procedure: Similar to as described in General Procedure Z, 6-fluoro-2,3-dihydro- 1H-indole-2,3-dione was converted to the title compound as a yellow solid (ig, 15%). LC-MS (ES, iWz): 195 [M+H]; A solution of 2,3-dihydro-1H-indole-2,3-dione (1 eq.) and sodium hydroxide (1.1 eq.) in water was stirred for 5-30 mm at 25 C. Then a solution of sodium nitrite (1 1 eq.) in water and concentrated sulfuric acid (2 eq.) were added dropwise with stirring at 0.-10 C. After 5-30 mm a solution of SnC12 (2.5 eq.) in concentrated hydrochloric acid (15-30 eq.) was added slowly. After5 being stirred for 1–5 h at 25 C the reaction mixture was filtered and the solid was dissolved in methanol. Sulfuric acid (0.5-1 eq.) was added to the solution and the solution was heated to reflux overnight. The resulting mixture was concentrated under vacuum, diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum to give the ester which may need further purification such as fresh chromatography.

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; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 126674-93-9, name is 4,6-Difluoro-1H-indole-2,3-dione, molecular formula is C8H3F2NO2, 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 4,6-Difluoro-1H-indole-2,3-dione

Stage 3: 2-amino-4,6-difluorobenzoic acid First sodium hydroxide (6.70 g, 167 mmol) and then 30% hydrogen peroxide (6.7 ml) in water (60 ml) were added to a suspension of the product from stage 2 (4.58 g, 25 mmol) in water (125 ml) at 0 C. The mixture was stirred at room temperature for 20 h and then brought to pH 3 with formic acid (approx. 11 ml, severe foaming), during which the title compound precipitated out. The mixture was then filtered and product was dried over phosphorus pentoxide in a desiccator. Yield: 3.72 g (86%), white solid. Melting point: 198-202 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 126674-93-9, its application will become more common.

Reference:
Patent; Gruenenthal GmbH; US2008/293749; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 61-70-1, 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 61-70-1 as follows.

N-methyloxindole (0.5 g, 3.4 mmol) in acetonitrile(5 mL) was stirred at 0C, and then NBS (0.62 g) in 10 mL acetonitrile was added dropwise. The mixture was stirred at that temperature for 1h and then stirred for 2h at ambienttemperature. Then the solution was evaporated and the solid was dissolved in CHCl3,washed twice with water. After CHCl3 was evaporated, the brown solid was recrystallizedwith hexane. 5-bromo-N-methyloxindole (0.44 g) was prepared in 58% yield.1H-NMR (300MHz, CDCl3) delta(ppm) : 7.42-7.39 (d, 1H), 7.26 (s, 1H), 6.71-6.68 (d,1H), 3.52-3.20 (s, 2H), 3.19 (s, 3H).

According to the analysis of related databases, 61-70-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kang, Hyeonmi; Lee, Hayoon; Shin, Hwangyu; Kang, Seokwoo; Kim, Beomjin; Park, Jongwook; Molecular Crystals and Liquid Crystals; vol. 618; 1; (2015); p. 47 – 54;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 959235-95-1,Some common heterocyclic compound, 959235-95-1, name is 6-(Trifluoromethoxy)indoline, molecular formula is C9H8F3NO, 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 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (590 mg, 2.9 mmol), 2-(2-(4-(fe/t-butoxy)-4-oxobutoxy)-4-chlorophenyl)-2-((3-methoxy-5-(1 /-/-1 ,2,4- triazol-1 -yl)phenyl)amino)acetic acid 11d (1 .5 g, 2.9 mmol), HATU (1 .65 g, 4.35 mmol) and diisopropylethylannine (1 .45 mL, 8.7 mmol) in DMF (60 mL) was stirred at room temperature for 12 h. The mixture was diluted with water. The precipitate was filtered off, washed with water and taken up with EtOAc. The organic layer was washed with water, dried over MgSO4, filtered and the solvent wasconcentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (15-40 muiotatauiota, 120 g, heptane/EtOAc 60/40). The pure fractions were combined and concentrated to dryness to give, after crystallization from ether/diisopropyl ether, terf-butyl 4-(5-chloro-2-(1 -((3-methoxy-5-(1 H-1 ,2,4- triazol-1 -yl)phenyl)amino)-2-oxo-2-(6-(trifluoromethoxy)indolin-1 -yl)ethyl)phenoxy)- butanoate 13a (1 .05 g).

The synthetic route of 959235-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; COESEMANS, Erwin; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; BARDIOT, Dorothee Alice Marie-Eve; (92 pag.)WO2018/178240; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 39603-24-2, 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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Isatin derivatives (S1) were synthesized by treating isatins with NaH and then reacting with methyl iodide or benzyl bromide or allyl bromide, respectively, in dry DMF at room temperature.

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, 5,7-Dimethylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Lin-Lin; Da, Bing-Chao; Xiang, Shao-Hua; Zhu, Shuai; Yuan, Zi-Yun; Guo, Zhen; Tan, Bin; Tetrahedron; vol. 75; 12; (2019); p. 1689 – 1696;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 141452-01-9, 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. 141452-01-9, name is Methyl indoline-5-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 2: Methyl 1- (3, 4, 5-Trimethoxy-benzyl)-2, 3-DIHYDRO-LH-INDOLE-5-CARBOXYLATE (21); [0193] To a solution of 20 (300 mg, 1.69 MMOL), 3,4, 5-trimethoxybenzaldehyde (365 mg, 1.86 MMOL) and dibutyltin dichloride (51 mg, 0.17 MMOL) in THF (8 mL) was added phenylsilane (229 ss 1.86 MMOL). The mixture was stirred overnight at room temperature under nitrogen. Additional aldehyde and PHENYLSILANE were added and the stirring continued until starting material was consumed. THF was evaporated in vacuum and the residue was purified by flash chromatography (eluent 20% EtOAc in hexane). The compound was further purified by re-crystallization in a mixture EtOAc/hexane and finally by a second flash chromatography (eluent 20% EtOAc in hexane) to give the title compound 21 (428 mg, 71%) as a white SOLID. H-NMR (DMSO) 8 : 2.96 (t, J = 8.4 Hz, 2H); 3.45 (t, J = 8.7 Hz, 2H); 3.61 (s, 3H); 3.71 (s, 6H); 3.72 (s, 3H); 4.30 (s, 2H); 6.59 (s, 2H); 6.61 (d, J = 8.4 Hz, 1H), 7.54 (d, J = 1. 6 Hz, 1H); 7.63 (dd, J = 1.8, 8.4 Hz, 1H).

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

Reference:
Patent; METHYLGENE, INC.; WO2005/30704; (2005); 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H6BrNO2

General procedure: To a flame-dried screw-capped test tube equipped with a magnetic stir bar was added I, 4,7,10,13, 16-hexaoxacyclooctadecane (0.396 g, 1.5 mmol), KF (0.087 g, 1.5 mmol) and 1- methylindoline-2,3-dione 3 (0.50 mmol). Then the screw-capped tube was evacuated and backfilled with argon. The mixture was dissolved in THF (2.0 mL) under argon atmosphere. The resultant reaction mixture was kept stirring at 30 C for 5 min. To the stirring solution was added pyridine 7 (0.75 mmol) and the aryne precursor 2 (0.75 mmol). When TLC control showed the completion of the reaction (typically after 12 h), the reaction stopped and the crude reaction mixture was purified by column chromatography on silica gel to afford the corresponding indolin 2-one derivatives 8 in good yields.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 2058-72-2.

Reference:
Patent; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; THANKAPPAN, Biju Akkattu; BHUNIA, Anup; ROY, Tony; WO2014/184808; (2014); 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 3676-85-5 as follows. Recommanded Product: 5-Aminoisoindoline-1,3-dione

General procedure: To a solution of substituted heteroaromatic amine (1.00 mmol) in dichloromethane, DMF or THF (2 mL) triethylamine (1.10 mmol) was added. The mixture was cooled in an ice bath and acryloyl chloride (1.05 mmol) was added dropwise. The reaction mixture was stirred for 24 hours at room temperature and extracted with water (3 × 3 mL). Subsequently, the aqueous layer was extracted with ethyl ether (3 × 5 mL). The combined organic layers were dried over anhydrous MgSO4 and filtered. After evaporation of solvents, the residue was purified on a silica column with chloroform:methanol mixtures (100:1, 50:1 v/v) as eluents to afford the respective acrylamides 10.

According to the analysis of related databases, 3676-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kokosza, Kamil; Balzarini, Jan; Piotrowska, Dorota G.; Nucleosides, nucleotides and nucleic acids; vol. 33; 8; (2014); p. 552 – 582;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 169037-23-4, 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 162 STR184 Step 1. Preparation of 2-amino-5-(trifluoromethoxy)benzoic acid. 5-(Trifluoromethoxy)isatin (15.0 g, 65 mmol) and potassium hydroxide pellets (4 g) were mixed in water (35 mL) and cooled to 0 C. With vigorous stirring, a solution of 30% aqueous hydrogen peroxide (11.7 g), potassium hydroxide pellets (5.8 g), and water (80 mL) was added drop-wise keeping the temperature below 10 C. After stirring 1 hour at 0 C., glacial acetic acid (22 mL) was added drop-wise, causing foaming and formation of a precipitate. The contents were stirred overnight and filtered to afford the 2-amino-5-trifluoromethoxybenzoic acid as an amber solid (12.5 g, 87%). A small amount was recrystallized from ethyl acetate-hexanes to afford amber needles for an analytical sample and the remaining compound was used without further purification: mp 142.5-144.2 C. 1 H NMR (CDCl3, 300 MHz) 7.98 (s, 1H), 7.18 (d, 1H, J=8.0 Hz) 6.62 (d, 1H, J=8.0 Hz), 6.40 (brs, 2H). Anal. Calc’d for C8 H6 NO3 F3: C, 43.45; H, 2.73; N, 6.33. Found: C, 43.40; H, 2.65; N, 6.35.

The synthetic route of 5-(Trifluoromethoxy)indoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G.D. Searle & Co.; US6034256; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 337536-15-9, name is 4-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-Bromoisoindolin-1-one

EXAMPLE 1D 4-(4-aminophenyl)-1-isoindolinone A suspension of Example 1C (2 g, 9.43 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxa-borolan-2-yl)aniline (2.5 g, 11.3 mmol), and Na2CO3 (2.2 g, 20.8 mmol) in DME (68 mL) and water (17 mL) was purged with nitrogen, treated with Pd(PPh3)4 (1 g, 0.9 mmol), and stirred at 90 C. for 19 hours. The reaction mixture was cooled to room temperature, concentrated to one-third its original volume, diluted with ethyl acetate (30 mL) and water (20 mL), and filtered. The filter cake was washed with water and ethyl acetate and dried to give 1.25 g of the desired product. MS (ESI(+)) m/e 225 (M+H)+.

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

Reference:
Patent; Curtin, Michael L.; Davidsen, Steven K.; Frey, Robin R.; Heyman, Howard R.; Holms, James H.; Michaelides, Michael; Steinman, Douglas H.; US2005/26976; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem