Month: June 2021

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. category: indolines-derivatives

Example 1; Methylene chloride (200 ml) is added to 1-(1 ,2-Benzisothiazol-3- yl)piperazine (15 gm), stirred for 10 minutes and then triethylamine (22 ml) is added drop wise for 10 minutes. Trimethylsilyl chloride (15 ml) is added drop wise to the reaction mass for 20 minutes, tetrabutyl ammonium bromide (5 gm) is added and stirred for 1 hour at 25-300C. Then the reaction mass is heated to 400C and methylene chloride is distilled under vacuum. To this reaction mass sodium carbonate (16 gm) and 5-(2-chloroethyl)-6-chloro-oxindole (16 gm) are added, stirred for 10 minutes and added water (400 ml) and sodium iodide (2 gm). The contents are heated to 1000C and stirred for 7 hours 30 minutes at 95 – 1000C. Solid is filtered and slurried in 200 ml of water, filtered and washed with water (100 ml). Then the solid is slurried in isopropyl alcohol (75 ml) at reflux, refluxed for 1 hour and then filtered the solid at reflux point to give 15 gm of ziprasidone (HPLC purity: 98.36%).

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; HETERO DRUGS LIMITED; WO2006/80025; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 15861-30-0, These common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, 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.

2, 3-Dihydro-1H-indole-5-carboxylic acid (12.4 mmol) was dissolved in DMF (5 mL) and 1, 2-dichloroethane (40 mL). DIPEA (12.4 mmol), 1- (3-dimethylaminopropyl)- 3-ethyl-carbodiimide hydrochloride (12.4 mmol), 1-hydroxybenzotriazole (12.4 mmol) and 2-aminothiazole (12.4 mmol) was added. Stirred at 50 C for 48h. HC1 (2M) (12.4 mmol) was added to the reaction mixture followed by water (30 mL). This gave a heavy precipitation which was removed by filtration. The solid was washed with water and 1,2-dichloroethane and dried. Yield: 56% 1H NMR (D6-DMSO) : 6.60 (s, 1H); 7.26 (d, 1H); 7.44-7. 54 (2H); 7.56 (d, 1H); 7. 86 (d, 1H); 8.45 (s, 1H) ; 11.51 (br s, 1H).

The synthetic route of 15861-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. LUNDBECK A/S; WO2005/39572; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 114041-16-6, 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 114041-16-6 as follows.

General procedure: Compound 8 (70.6 mg, 0.24 mmol) and 5,6-dimethoxyisoindoline(68.5 mg, 0.38 mmol) were dissolved in CH3CN (30 mL), followed by addition of K2CO3 (138.8 mg, 1.00 mmol). The mixture was heated under reflux and stirred at 90 C for 6 h. After cooling and filtration, the solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate/triethyamine) = 10:10:1, v/v/v) to afford 13(56.8 mg, 59%)

According to the analysis of related databases, 114041-16-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Liang; Ye, Jiajun; He, Yingfang; Deuther-Conrad, Winnie; Zhang, Jinming; Zhang, Xiaojun; Cui, Mengchao; Steinbach, Joerg; Huang, Yiyun; Brust, Peter; Jia, Hongmei; Bioorganic and Medicinal Chemistry; vol. 25; 14; (2017); p. 3792 – 3802;,
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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-(2-Oxopropyl)isoindoline-1,3-dione

Example 491; N-[7-(3-Fluoro-benzenesulfonyl)-1-methyl-1 ,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmeth isobutyramideStep 1 :2-(7-lodo-1-methyl-1 ,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl)- isoindole-1 ,3-dione To a mixture of 2-(6-iodo-benzofuran-3-yl)-ethylamine (2.00 g, 6.97 mmol) and 2-(2-oxo-propyl)- isoindole-1 ,3-dione (4.25 g, 20.9 mmol) was added trifluoroacetic acid (8.00 mL, 104 mmol) and then heated at 80 C . After 16 h, additional ketone (3 eq) was added and heating continued. After a total of 3 days, the reaction mixture was basified (DCM-aq. NaHC03) and the resulting precipitate was filtered, rinsed with DCM and dried to give an off-white solid, mp 302-304 C dec; MS m/z 473 [M + H]+.

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEPHALON, INC.; BACON, Edward R.; BAILEY, Thomas R.; DUNN, Derek D.; HOSTETLER, Greg A.; MCHUGH, Robert J.; MORTON, George C.; ROSSE, Gerard C.; SALVINO, Joseph M.; SUNDAR, Babu G.; TRIPATHY, Rabindranath; WO2011/87712; (2011); A2;,
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. 2518-24-3, name is 4-Aminoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

Step 1: Preparation of 4-amino-7-bromoisoindolin-1,3-dione (38) To a solution of 4-aminoisoindolin-1,3-dione (37) (0.5 g, 3.08 mmol) in MeOH (50 mL) was added a mixture of NBS (0.58 g, 3.24 mmol) as three portions at room temperature. Then, the mixture thus obtained was stirred at room temperature for 8 hours, and filtered. The filtrate was concentrated to give the crude product of 4-aminoisoindolin-1,3-dione 38 (0.42 g) as a solid, which was directly used in the next step without further purification.

The synthetic route of 2518-24-3 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

Synthetic Route of 954-81-4, These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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.

(cis) 1-(1 /-/-Benzimidazol-2-ylmethyl)-1 ,2,3,4,4a,5,6,10b-octahydro-1 ,10- phenanthroline (0.045 g, 0.14 mmol), 2-(5-bromopentyl)-1 /-/-isoindole-1 ,3(2H)-dione (0.062 g, 0.21 mmol), potassium iodide (5 mg), and N,N-diisopropylethylamine (0.050 g, 0.31 mmol) in 3 mL of dimethylformamide were heated to 80 9C for 16 hours. The mixture was allowed to cool to room temperature and hydrazine (0.4 mL, 14.0 mmol) was added. The mixture stirred at room temperature overnight. The mixture was quenched with water and extracted 3 times with ethyl ether. The ether layers were combined, dried over sodium sulfate, and concentrated. The residue was purified by silica chromatography eluting with a 0% to 10% gradient of 30% aqueous ammonium hydroxide in acetonitrile to yield 0.01O g (18%) of (cis)-5-[2-(3,4,4a,5,6,10b- hexahydro-1 ,10-phenanthrolin-1 (2/-/)-ylmethyl)-1 H-benzimidazol-1-yl]-1- pentanamine. 1H NMR (400 MHz, METHANOL-D4) delta ppm 1.0 (m, 2 H), 1.3 (m, 3 EPO H), 1.4 (s, 2 H), 1.6 (m, 1 H), 1.7 (m, 2 H)1 2.1 (m, 1 H), 2.3 (m, 2 H), 2.5 (m, 3 H), 2.8 (m, 1 H), 2.9 (m, 1 H), 3.1 (m, 1 H), 3.4 (s, 1 H), 3.5 (d, J=13.9 Hz, 1 H), 3.9 (m, 1 H), 4.1 (m, 1 H), 4.2 (d, J=13.9 Hz, 1 H), 7.2 (m, 2 H), 7.3 (m, 2 H), 7.5 (d, J=7.1 Hz, 1 H), 7.7 (d, J=7.9 Hz, 1 H), 8.4 (s, 1 H); MS m/z404 (M+1).

Statistics shows that N-(5-Bromopentyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 954-81-4.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/96444; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1127-59-9, A common heterocyclic compound, 1127-59-9, name is 7-Methylindoline-2,3-dione, molecular formula is C9H7NO2, 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 chemical synthesis route of the target IBT compounds is illustrated in Scheme 1. The IBTs 3 were synthesized by the reaction of isatin 1 and N-phenylhydrazinecarbothioamide 2 in an aqueous solution of ethanol and acetic acid under reflux [22,23]. Generally, equivalent 1 and 2 was dissolved in a solution of acetic acid/water/alcohol solution, and then the mixture was refluxed for approximate 5-6 h. The reaction mixture was subsequently cooled to room temperature and in most cases a yellow or orange solid precipitated out. This precipitate was filtered, washed with water, and then dried to give a crude product. Recrystallization from ethanol gave pure solid in high yields. 4.2.19 (Z)-N-(4-Fluorophenyl)-2-(7-methyl-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (3-19) Yield 70percent; m.p.: 242-244 °C; yellow solid; 1H NMR (DMSO-d6, 400 MHz), delta 12.89 (s, 1H, NNH), 11.33 (s, 1H, NH), 10.84 (s, 1H, SCNH), 7.68-7.66 (m, 2H, J = 8.0 Hz, Ar2-H3 and Ar2-H5), 7.61 (d, 1H J = 7.2 Hz, Ar1-H4), 7.49-7.48 (m, 2H, J = 4.4 Hz, Ar2-H2 and Ar2-H6), 7.20 (d, 1H J = 7.2 Hz, Ar1-H6), 7.03 (t, 1H J = 7.6 Hz, Ar1-H5), 2.24 (s, 3H, CH3); 13C NMR (DMSO-d6, 101 MHz), delta 176.3, 163.1, 141.1, 137.4, 132.9, 132.7, 130.0, 128.2, 127.2, 122.3, 120.5, 119.4, 118.8, 15.8; IR: (KBr, nu/cm-1), 3308 (NN-H), 3165 (CON-H), 3052 (Ar-H), 1695 (-CONH-), 1625 (C=N), 1572 and 1539 (Ar-C=C), 1209 (C=S), 1153 (N-N); Elemental analysis calculated for C16H13FN4OS, C: 58.52, H: 3.99, N: 17.06, found C: 58.75, H: 3.66, N: 17.45.

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, Xu-Meng; Guo, Hui; Li, Zai-Shun; Song, Fu-Hang; Wang, Wei-Min; Dai, Huan-Qin; Zhang, Li-Xin; Wang, Jian-Guo; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 419 – 430;,
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. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

4.92 g (0.03 mol) of 6-nitro-2,3-dihydro-1H-indole (16) was dispersed in 50 ml of dimethylformamide under nitrogen atmosphere and stirred at room temperature for about 10 minutes. Then, 5.3 g mol) and 6.1 ml (0.036 mol) of diisopropylethylamine (DIPEA) were successively added to the reaction mixture. The reaction solution was gradually heated and stirred at 70 C for 4 hours to complete the reaction. After cooling the reaction mixture to room temperature, 100 ml of distilled water and 200 ml of ethyl acetate were added and the mixture was stirred for 30 minutes. The organic layer was separated and washed with H 2 O. The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure 7.41 g (97.2%) of 6-nitro-2,3-dihydro-1- (1-phenylmethyl) -1H-indole (73) as a yellowish liquid was obtained.

According to the analysis of related databases, 19727-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Korea Research Institute of Chemical Technology; Shin Seung-rim; Jeon Geun; Shin Jong-il; Park Yeong-il; Ahn Gyeong-ryong; (48 pag.)KR101842495; (2018); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 496-12-8, 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. 496-12-8, name is Isoindoline, This compound has unique chemical properties. The synthetic route is as follows.

Alternatively the amino compounds of the present invention can be synthesized applying Weinreb-rype chemistry (Tetrahedron Letters 2000, 41(8): 1141). As an example, the commercially available isoindoline 2 can be coupled to a commercially available N-protected amino ester (e.g., N-(diphenylmethylene)glycine ethyl ester ) 5 to form the amide 6 by first treating the amine 2 with an organo aluminum species such as trimethyl aluminum and adding the resulting organometallic intermediate to the protected amino ester 5 in an appropriate solvent such as DCM. Treatment of 6 with benzylbromide in the presence of a phase transfer catalyst (e.g., tetrabutylammonium bromide, TBAB) and a suitable base (e.g., potassium hydroxide, KOH) and a solvent such as DCM yields 7, (Journal of the American Chemical Society, 1989, 111(6):2353), which upon treatment with an acid (e.g., HCl) in a suitable solvent such as DCM produces 8, a compound of the present invention; To a solution of isoindoline (690 mg, 5.79 mmol) in DCM (5 ml) is added a 2M solution of trimethyl aluminum in heptane (2.9 ml, 5.79 mmol) and the resulting solution is allowed to stir at ambient temperature for 30 minutes. To this solution is added a solution of (benzhydrylidene-amino)-acetic acid ethyl ester (1.29 g, 4.82 mmol) in DCM (5 ml). The reaction is allowed to stir at ambient temperature for 18 h and carefully quenched with a 10% aqueous solution of citric acid. The resulting biphasic mixture is diluted with DCM (10 ml) and extracted with a saturated solution of Rochelle’s Salt (10 ml). The organic layer is separated, concentrated in vacuo and purified by column chromatography (hexanes-ethyl acetate 7-70%) resulting in 2- (Benzhydrylidene-amino)-l-(l,3-dihydro-isoindol-2-yl)-ethanone (1.0 g, 61%). 2-(Benzhydrylidene- amino)-l-(l,3-dihydro-isoindol-2-yl)-ethanone is analyzed by HPLC/Mass Spec.

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

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/38459; (2007); A2;,
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. 13220-46-7, name is 4-Methylindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Methylindolin-2-one

Example 83 (S,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylidene)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one (S)-5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 78f (40 mg, 0.12 mmol 1) and 4-methyl-1,3-dihydro-indol-2-one (18 mg, 0.12 mmol) were dissolved in 1.5 ml of ethanol, and added with 6 mul of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred at 45 C. for 16 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature, and filtered. The filter cake was washed with anhydrous ethanol (1 ml*2) and dried to obtain the title compound (S,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylidene)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one 83 (35 mg, yield 63.6%) as a yellow solid.

According to the analysis of related databases, 13220-46-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ChoTang, Peng Cho; Su, Yidong; Li, Yali; Zhang, Lei; Zhao, Fuqiang; Yang, Jialiang; Zhou, Ying; Bie, Pingyan; Qian, Guangtao; Ju, Minggang; US2010/75952; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem