Month: February 2021

Electric Literature of 15861-30-0, A common heterocyclic compound, 15861-30-0, name is Indoline-5-carboxylic acid, 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.

Reference Example 1 Synthesis of 1-carbobenzoxy-5-carboxyindoline To a mixture of water (20 ml) and diethyl ether (20 ml) were added 5-carboxyindoline (2.0 g) and sodium hydroxide (0.6 g), and then, under ice-water cooling, carbobenzoxy chloride (2.59 g) and water (10 ml) containing sodium hydroxide (2.1 g) were added to the mixture thereto alternatively. The mixture was stirred at room temperature for 2 hours. The reaction mixture was made acidic with 2N-hydrochloric acid and precipitated crystals were collected by filtration. Precipitates were washed with ether and air-dried to obtain the title compound (2.8 g). 1 H-NMR (DMSO-d6, delta): 3.10 (2H, t, J=8 Hz), 4.03 (2H, t, J=8 Hz), 5.23 (2H, s), 7.2-8.0 (8H, m). mp; 194-196 C.

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

Reference:
Patent; Chugai Seiyaku Kabushiki Kaisha; US5354753; (1994); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 19727-83-4, 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. 19727-83-4, name is 6-Nitroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step A-Preparation of 1-(6-nitroindolinyl)-2-piperidylethan-1-one 6-Nitroindoline (2.5 g) was dissolved in 200 mL of CH2Cl2, followed by DIEA (2.5 g).The mixture was cooled down to 0 C. in ice bath.chloroacetyl chloride (1.7 g) in 20 mL CH2Cl2 was added dropwise to the mixture over 10 min and the mixture was stirred at RT overnight.The mixture was extracted once with saturated NaHCO3 solution and once with brine, the resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo.The crude material was purified by flash chromatography on silica gel with 3:2 hexane:EtOAc to afford a yellow oil (1.4 g) which was added to piperidine (5 mL), followed by NaI (100 mg).The mixture was heated at 70 C. overnight then concentrated in vacuo and extracted between EtOAc and saturated NaHCO3 solution, the organic layer was washed with brine, the resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo.The crude material was purified by flash chromatography on silica gel with 9:1 EtOAc:MeOH to afford a yellow oil. MS: 290 (M+1). Calc’d. for C15H19N3O3-289.33.

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-Nitroindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Amgen Inc.; US2003/225106; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7223-50-9, name is N-Propargylphthalimide, 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 7223-50-9, SDS of cas: 7223-50-9

General procedure: To a solution of alkyne (1.0 mmol) in PEG-400/H2O(4:1) was added [Ru(p-cymene)Cl2]2 (0.01 mmol), and themixture stirred at room temperature. Upon completion of thereaction (monitoring by TLC), the reaction mixture was dilutedwith Et2O (10 mL), stirred for 10 min, and allowed to stand in anice-salt bath to solidify the PEG-400. The organic layer wasdecanted, dried over anhydrous Na2SO4, filtered, and concentratedunder reduced pressure. The residue obtained was purifiedby silica gel flash column chromatography (ethyl acetate-petroleum ether) to give the pure product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-Propargylphthalimide, and friends who are interested can also refer to it.

Reference:
Article; Mainkar, Prathama S.; Chippala, Venkataraju; Chegondi, Rambabu; Chandrasekhar, Srivari; Synlett; vol. 27; 13; (2016); p. 1969 – 1972;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 366453-22-7,Some common heterocyclic compound, 366453-22-7, name is 4-Methoxyisoindolin-1-one, molecular formula is C9H9NO2, 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 an ice-cold solution of 2c (291 mg, 1.78 mmol) in CH2Cl2 (20 mL) was added a 1.0 M BBr3 solution in CH2Cl2 (3.6 mL, 3.6 mmol). The cold bath was then removed and the resulting solution was stirred for 16 h at ambient temperature. The reaction was carefully quenched by addition of water and the mixture was extracted with EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), filtered and evaporated to dryness to give 2d (232 mg, 87% yield) as beige solid.

The synthetic route of 366453-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim (Canada) Ltd.; US2004/106791; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 611-09-6,Some common heterocyclic compound, 611-09-6, name is 5-Nitroindoline-2,3-dione, molecular formula is C8H4N2O4, 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 acetophenone or isatin (5 mmol) in THF (10 mL), BF3¡¤OEt2 (7.5 mmol) was added at 0C under the atmosphere of N2 and the mixture was stirred for 10 minutes. To the cooled mixture, anhydrous hydrazine (7.5 mmol) was added in one portion and the reaction mixture was stirred at 0C under the atmosphere of N2 for 30 min. The reaction was quenched by the addition of a saturated solution of NH4Cl (4 mL), extracted by ethyl acetate (3 ¡Á 15 mL) and purified by column chromatography (ethyl acetate-CH2Cl2; 3 : 7) to afford hydrazones 2-22.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Nitroindoline-2,3-dione, its application will become more common.

Reference:
Article; El-Azab; Ghabbour; El-Husseiny; Maarouf; Mohamed; Abdel-Aziz; Russian Journal of General Chemistry; vol. 86; 12; (2016); p. 2837 – 2844; Zh. Obshch. Khim.; vol. 86; 12; (2016); p. 2837 – 2844,8;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20870-90-0, 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. 20870-90-0 name is 5-Bromo-1-methyl-2-oxoindoline, 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.

11. Preparation of I -methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)indolin-2-one 5-Bromo-1-methylindolin-2-one (537 mg, 2.375 mmol),bis(pmnacolate)diborane (987 mg, 3.89 mmol), potassium acetate (636mg, 6.48 mmol) and Pd(dppf)C12.CH2CI2 (88 mg, 0.108 mmol) wereloaded in a microwave vial and DME (15.6 ml) was added. The reaction mixture was heated at 80 C overnight and was then concentrated. The crude was purified by chromatography on silica gel (biotage, CyHex/EtOAc) to give the product(500 mg, 85%). 1H-NMR (500 MHz, CDCI3) ppm = 7.78 (d, J=7.7, IH), 7.69 (s, IH), 6.84 (d, J7.7, IH), 3.52 (s, 2H), 3.24 (s, 3H), 1.36 (s, 12H). LC – MS (ESI, m/z) Rt = 2.90 mm- 274 (M-?-H) (HPLC method E).

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

Reference:
Patent; MERCK PATENT GMBH; CANCER RESEARCH TECHNOLOGY LIMITED; SCHIEMANN, Kai; STIEBER, Frank; CALDERINI, Michel; BLAGG, Julian; MALLINGER, Aurelie; WAALBOER, Dennis; RINK, Christian; CRUMPLER, Simon Ross; (127 pag.)WO2015/144290; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 19727-83-4, 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 19727-83-4 as follows.

General procedure: The suitable amine (1 equiv), pyridine (4 equiv) were dissolved in dichloromethane and 1,3,4-oxdiazole-sulfonyl chloride derivative (1.2 equiv) was added in drop wise at -2 oC to -7 oC. The organic reaction mixture was stirred at the room temperature for 2-4 h. After completion of the reaction, the reaction mixture was poured into ice water and was diluted with ethyl acetate, and washed with water, 2 M hydrochloric acid, 10% sodium bicarbonate, brine water and dried with sodium sulfate. It was concentrated under reduced pressure to afforded sulfonamide as product [32].

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:
Article; Kavitha, Selvaraj; Nasarullah, Zulfareen; Kannan, Kulanthai; Bulletin of the Chemical Society of Ethiopia; vol. 33; 2; (2019); p. 307 – 319;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 41910-64-9, These common heterocyclic compound, 41910-64-9, name is 4-Chloroindoline, 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 solution of XlntOI and an oxetane aldehyde derivative Y in methanol was stirred for 3 hours at room temperature. Sodium cyano borohydride was added at 0C and the mixture was stirred for another 3 hours at room temperature. The solvent was removed and the residue was diluted with water and extracted with ethyl acetate. The combined organic layer was washed with water, brine solution, dried over sodium sulfate andconcentrated under reduced pressure to give the crude compound.Purification by column chromatography with 3% ethyl acetate / hexane yielded XYInt02.Synthesised according to the procedure disclosed in Example 1 where X is 4- chloro indole, Y is 3-hydroxyoxetane-3-carbaldehyde, and Z is 2- cyclopentylacetic acid. Formula: C19H23CIN203; Molecular Weight: 362.85; Mass/charge ratio: 362.14 (100.0%), 364.14 (32.7%), 363.14 (21.4%), 365.14 (6.7%), 364.15 (2.1 %); Elemental analysis: C, 62.89; H, 6.39; CI, 9.77; N, 7.72; O, 13.23.

Statistics shows that 4-Chloroindoline is playing an increasingly important role. we look forward to future research findings about 41910-64-9.

Reference:
Patent; AFFECTIS PHARMACEUTICALS AG; BOES, Michael; WO2012/163456; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6326-79-0, A common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, molecular formula is C8H4BrNO2, 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: Isatins (1a-j, 3.0 g), hydrazine hydrate (80%, 13 mL) and water (13 mL) were added to a flask equipped with a thermometer with vigorous stirring. The reaction mixture was kept at 140 C in an oil bath for 6 h before being cooled to r.t., when hydrochloric acid (2.0 mol L-1) was added to bring the pH to pH 2. The reaction mixture was stirred at r.t. for 12 h. Compounds 2a-j were obtained by filtering under vacuum and recrystallisation from absolute ethanol.

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, Chao; Xu, Juan; Zhao, Xinyu; Kang, Congmin; Journal of Chemical Research; vol. 41; 9; (2017); p. 537 – 540;,
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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., COA of Formula: C8H8N2O2

REFERENCE EXAMPLE 6; 5-Amino-1-isopropy.sulfonylindofine; a) 1-isopropy.sulfonyf~5-?itroindoline; 1 mL of TEA (7.61 mmol) and isopropylsulfonyl chloride (0.5 mL, 4.57 mmoi) were added at 0 0C to a solution of 5-nitroindoline (0.5 g, 3.05 mmol) in CH 2Cl2 (50 mL). The reaction mixture was stirred at room temperature for 48 h and then at reflux temperature for 18 h. The crude product obtained was diluted with a saturated aqueous solution of NaHCOs and extracted thrice with CH2Cl2. The combined organic phases were separated, dried over Na2SO4 and the solvent was evaporated to dryness. The desired compound was obtained in quantitative yield and used in next step without further purification.

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PALAU PHARMA, S.A.; SALAS SOLANA, Jorge; ALMANSA ROSALES, Carmen; SOLIVA SOLIVA, Robert; FONTES USTRELL, Montserrat; COMELLES ESPUGA, Josep; WO2010/34740; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem