Category: indolines-derivatives

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. 317-20-4, name is 7-Fluoroisatin, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 317-20-4

General procedure: The mixture of isatin (1 mmol), 3-amino-1-phenyl-1H-pyrazol-5(4H)-one (1 mmol), 1,2-diarylethan-1-one, 2,3-dihydroinden-1-one (1 mmol) or 3,4-dihydronaphthalen-1(2H)-one (1 mmol), H2O (6 mL), HOAc (2 mL) was put in a reaction flask under 90 C about 5-7 h (monitored by TLC). After completion, the reaction mixture was cooled to room temperature and the products would be isolated out at same time. Then, compound 4 was recrystallized from DMF, however, the pure products of 6 and 8 were filtered from water, dried, without further recrystallization.

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 317-20-4.

Reference:
Article; Wang, Zhansheng; Gao, Lingli; Xu, Zhongyun; Ling, Zhi; Qin, Yaqi; Rong, Liangce; Tu, Shu-Jiang; Tetrahedron; vol. 73; 4; (2017); p. 385 – 394;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18711-15-4, name is 4,6-Dichloroisatin, 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 18711-15-4, HPLC of Formula: C8H3Cl2NO2

General procedure: A solution of 4,6-dichloroisatine (7.2 g, 33 mmol) in THF (120 ml) was dropwise added under nitrogen atmosphere to 3,4-dichlorophenylmagnesium bromide (200 ml, 0.5 M in THF). The mixture was stirred 4 h at 70 C, then NH4Claq was added. After extraction in EtOAc, the organic phase was washed three times with NaOH 1 N, then dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (cyclohexane/EtOAc = 8/2) to give 11 (6.73 g, 56%) as a white solid.

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; Puleo, Letizia; Marini, Pietro; Avallone, Roberta; Zanchet, Marco; Bandiera, Silvio; Baroni, Marco; Croci, Tiziano; Bioorganic and Medicinal Chemistry; vol. 20; 18; (2012); p. 5623 – 5636;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 52537-00-5, name is 6-Chloro-2,3-dihydro-1H-indole, 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 52537-00-5, Quality Control of 6-Chloro-2,3-dihydro-1H-indole

EXAMPLE 40 Preparation of 1-Chloro-4,5,8,9,10,11-hexahydro-7H-azepino[4,5-b]pyrrolo[3,2,1-hi]indole Maleic Acid Following the general procedure outlined in EXAMPLE 14, and making non-critical variations but starting with 6-chloro-indoline, the title compound was obtained (amorphous solid). 1H NMR (CD3OD) 6.91, 6.81, 6.77, 4.90, 3.69, 3.34, 3.21; MS (ESI+) for C14H15ClN2 m/z 247.2 (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, 6-Chloro-2,3-dihydro-1H-indole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pharmacia & Upjohn Company; US6407092; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3485-84-5,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.

To a stirred solution of 4-bromo-Lambda/-(3,4-dimethoxyphenyl)benzenesulfonamide181 (887 mg, 2.39 mmol) in dimethylformamide (20 mL) at room temperature was added vinyl phthalamide (414 mg, 2 39 mmol), Pd2dba3 (131 mg, 0.143 mmol), tri-o-tolylphosphine(87 mg, 0 287 mmol), and t?ethylamine (0 83 mL, 5.98 mmol). The resulting solution was heated to 100 0C for 16 hours prior to cooling, dilution with brine, adjustment to pH = 2 with HCI, and extraction with ethyl acetate. The combined organic extracts were dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography using EtOAc (0-100%) in hexanes to afford 184 (285 mg, 26%) as a light yellow solid. LRMS(ESI): (calc) 464.5; (found) 465.2 (MH)+

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

Reference:
Patent; METHYLGENE INC.; WO2006/102760; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-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 3783-77-5, SDS of cas: 3783-77-5

b. 1-Bromo-4-phthalimidobutan-2-one (10a) To a suspension of 130 g (0.6 mole) of 4-phthalimido butan-2-one (7a) in 1000 ml of absolute methanol is added 96 g (0.6 mole) of bromine and the reaction mixture is stirred for 24 hours at room temperature. The precipitate, N-(4-bromo-3.3-dimethoxybutyl) phthalimide (8a) is filtered off, suspended in methanol and 30 ml of 10N sulfuric acid is added, after which the reaction mixture is heated until a clear solution is obtained. After cooling down the precipitate is collected and recrystallized from hot methanol. Yield 60%. Melting point: 120-122 C. (lit: R. G. Jones et al., J. Am. Chem. Soc., 72, 4526-4529 (1950), 119-120 C.). 1 H-NMR (CDCl3): 3.13 ppm., triplet, 2H (J=7.2 Hz); 3.92 ppm.,. singlet, 2H; 4.04 ppm., triplet (J=7.2 Hz), 2H; 7.60-7.96 ppm., multiplet, 4H.

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

Reference:
Patent; Cedona Pharmaceuticals B.V.; US5190589; (1993); A;,
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. 4403-36-5, name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, A new synthetic method of this compound is introduced below., Recommanded Product: 4403-36-5

To bis(4-methoxybenzyl)amine (Example 406.01, 3.37g, 13.10 mmol) and TEA (5.46 mL, 39.3 mmol) in DCM (109 mL) at 0 C was added 2-phthalimidoethanesulfonyl chloride (3.94 g, 14.41 mmol, commercially available from Matrix Scientific) slowly. The reaction was stirred at RT until complete by LCMS analysis. The reaction was diluted with a saturated solution of NaCl and extracted with DCM, dried over MgSO4, filtered and concentrated in vacuo. Purification of the residue by flash chromatography on a Versapak Spherical pre-packed silica gel column (Sigma-Aldrich, St. Louis, MO, eluent: 10-55% EtOAc/hexanes, gradient elution) provided Example 95.1 (4.04g, 62%) as a white solid after evaporation. The product was used directly in the next step without further purification.

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; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); 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. 480-91-1, name is Isoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H7NO

General procedure: A solution of POCl3 or POBr3 (30 mmol) in anhydrous DCM (7 mL) was added dropwise to DMF or DMA (30 mmol) in anhydrous DCM (15 mL) at 0 C. The mixture was stirred for 30 min at room temperature. Then, a solution of 1H-isoindolinone 1 (2 g, 15 mmol) in anhydrous DCM (75 mL) was added to the mixture, at 0 C. Subsequently, the reaction mixture was heated at reflux for 5 h, and then after cooling, the solvent was removed at reduced pressure. Ice-water was added, and the mixture was neutralized with NaOH 5 M. The precipitate was filtered out, washed with water and dried. The residue was recrystallized from MeOH/H2O (1:1) to give the following compounds.

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 480-91-1.

Reference:
Article; Diana, Patrizia; Martorana, Annamaria; Barraja, Paola; Montalbano, Alessandra; Carbone, Anna; Cirrincione, Girolamo; Tetrahedron; vol. 67; 11; (2011); p. 2072 – 2080;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 13220-46-7, name is 4-Methylindolin-2-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 13220-46-7, Recommanded Product: 13220-46-7

5-Iodo-4-methyl-2-oxindole To 2 g of 4-methyl-2-oxindole in 40 mL of glacial acetic acid in an ice bath was added 3.67 g N-iodosuccinimide. The mixture was stirred for 1 hour, diluted with 100 mL 50% acetic acid in water and filtered. The resulting white solid was dried under high vacuum to give 3.27 g (88% yield) of the title compound as an off-white solid.

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; Sugen, Inc.; US6486185; (2002); B1;; ; Patent; Sugen, Inc.; US6114371; (2000); A;,
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. 1337533-31-9, name is tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate, A new synthetic method of this compound is introduced below., name: tert-Butyl 5-bromo-4-fluoroindoline-1-carboxylate

1.1 -dimethylethyl 4-fluoro-5-(4.4.5.5-tetrameth yl-1.3.2-dioxaborolan-2-yl)-2.3-dih vdro-1H- indole- 1-carboxylateA mixture of 1 , 1-dimethylethyl 5-bromo-4-fluoro-2,3-dihydro-1 H-indole-1-carboxylate (1 g, 3.16 mmol), PdCI2(dppf)-CH2CI2 adduct (0.129 g, 0.158 mmol), potassium acetate (0.776 g, 7.91 mmol) and bis(pinacolato)diboron (0.803 g, 3.16 mmol) in 1 ,4-Dioxane (20 mL) was stirred at 100 C overnight on a stirrer hot-plate. LCMS indicated complete conversion to the desired product. The reaction mixture was poured into 1 :1 NaCI(aq. sat.): H20, (100 mL) and ethyl acetate (100 mL), shaken, and filtered through celite. The resulting mixture was separated and the aqueous layer was extracted with two additional portions of ethyl acetate (2 x 50 ml_). The combined organics were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (0- 25% EtOAc in hexanes, 40 g silica gel column) to afford 1 ,1 -dimethylethyl 4-fluoro-5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-2,3-dihydro-1 H-indole-1-carboxylate (660 mg, 57.4 % yield) as a pale yellow oil. LC-MS(ES) m/z = 308 [M+H-tBu]+. 1H NMR (400 MHz, DMSO-d6) delta 1.29 (s, 12 H), 1 .51 (s, 9 H), 3.05 (t, J = 8.72 Hz, 2 H), 3.98 (t, J = 8.72 Hz, 2 H), 7.22 – 7.61 (m, 2 H).

The synthetic route of 1337533-31-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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. Product Details of 20780-72-7

General procedure: A solution of 2-nitrobenzamides 1 or bis(2-nitrobenzamides) 4 (1 mmol), isatins 2 or acenaphthylene-1,2-diones 6 (1 mmol), and SnCl2*2H2O (4 mmol) in EtOH (5 mL) was stirred at reflux for 3-5 h. After this period, the TLC analysis of the mixture showed the reaction to be completed. The mixture was quenched with 3percent HCl (10 mL) and filtered to yield a crude product, which was purified by recrystallization from 95percent ethanol and DMF.

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

Reference:
Article; Hu, Yu; Wang, Man-Man; Chen, Hui; Shi, Da-Qing; Tetrahedron; vol. 67; 48; (2011); p. 9342 – 9346;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem