Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 1914-02-9, name is 3,3-Dimethylindoline, 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 1914-02-9, Application In Synthesis of 3,3-Dimethylindoline

3,3-DimethyM -(1 -methyl-4-piperidinyl)-2,3-dihydro-1 H-indole (D5) To a solution of 3,3-dimethyl-2,3-dihydro-1 /-/-indole (500 mg, 3.4 mmol) in acetic acid (5 ml) under an argon atmosphere was added 1-methyl-4-piperidinone (423 mg, 3.74 mmol) and after 5 minutes NaBH(OAc)3 (1.08 g, 5.1 mmol) was added in one portion. After 0.5 hours the mixture was diluted with water, basified with NaOH (pellets) until pH ca. 10 and extracted with Et2O. The organic phase was separated and dried over MgSO4. The solution was filtered and concentrated to afford 3,3-dimethyl-1-(1-methyl-4-piperidinyl)- 2,3-dihydro-1 H-indole (D5) in 94% yield (780 mg).1H-NMR (CDCI3): delta 1.27 (6H, s), 1.74 (4H, m), 2.04 (2H, dt), 2.30 (3H, s), 2.95 (2H1 d), 3.13 (2H, s), 3.35 (1 H, m), 6.40 (1 H, d, J=7.6 Hz), 6.63 (1 H, t, J=7.6 Hz), 6.98 (1 H, d, J=7.6 Hz), 7.04 (1H, t, J=7.6 Hz). MS: m/z (M+H)+ 245, C16H24N2 requires 244

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; GLAXO GROUP LIMITED; WO2006/38006; (2006); A2;,
Indoline – Wikipedia,
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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. 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 6-Amino-3,3-dimethylindolin-2-one

B. 6-(6-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ylamino)-3,3-dimethylindolin-2-one A mixture of 6-amino-3,3-dimethylindolin-2-one (156 mg), 4-chloro-6-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (100 mg), and CH3CN (5 mL) was run in a Microwave Reactor at 180 C. for 1 h. After cooling, the mixture was treated with sat. aq. Na2CO3 and extracted with EtOAc (30 mL*3). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by column to give an off-white solid (120 mg, 80%). 1H NMR (d6-DMSO): 10.32 (s, 1H), 8.54 (s, 1H), 8.40 (s, 1H), 8.28 (dd, 1H, J=5.2, 1.6 Hz), 7.89 (dd, 1H, J=8.0, 1.6 Hz), 7.30 (s, 1H), 7.19 (s, 2H), 7.08 (dd, 1H, J=8.0, 4.8 Hz), 4.38 (s, 2H), 3.61 (t, 2H, J=6.0 Hz), 2.88 (t, 2H, J=5.6 Hz), 1.24 (s, 6H).

The synthetic route of 100510-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kelly, Michael G.; Kincaid, John; Kaub, Carl J.; US2006/258689; (2006); 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. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 20870-79-5

To a suspension of 5-nitroindolin-2-one (5 g, 1 eq.) in EtOH(50 mL), activated carbon (1 g) and FeCl3 (1 g) were added.The mixture was heated to 78 C, and stirred for 10 min.Then 80% aqueous solution of hydrazine hydrate (8 eq.)was added dropwise into the reaction mixture in 5 min, theresulting mixture was stirred at 78 C for 8-10 h, thencooled to room temperature. The mixture was filtered to remove residue of activated carbon; the filtrate was concentratedunder vacuum to afford crude product, which waspurified by recrystallization from EtOH (about 15 mL) togive 5-aminoindolin-2-one as a pale yellow solid (yield91.9%).

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 20870-79-5.

Reference:
Article; Zhou, Yuanzheng; Ju, Yuan; Yang, Yang; Sang, Zitai; Wang, Zhenling; He, Gu; Yang, Tao; Luo, Youfu; Journal of Antibiotics; vol. 71; 10; (2018); p. 887 – 897;,
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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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., name: 2-(8-Bromooctyl)isoindoline-1,3-dione

A mixture of 2-(8-bromodecyl)isoindoline-1 ,3-dione (0.91 g, 2.70 mmol) and tris(4- methoxyphenyl)phosphine (1 g, 2.84 mmol) in MeCN (10 mL) was heated at 70 °C overnight. On cooling the solvent was removed in vacuo and the resulting residue purified by column chromatography eluting with 10percent MeOH in DCM to give [8-(1 ,3-dioxo-2,3- dihydro-1 H-isoindol-2-yl)octyl]tris(4-methoxyphenyl)phosphonium bromide (1 .56 g, 82percent) as a white foam. 1 H NMR (Method A) (DMSO-d6): delta (delta) ppm 7.88-7.81 (4H, m), 7.65 (6H, m), 7.28 (6H, m), 3.88 (9H, s), 3.54 (2H, t), 3.31 (2H, m), 1 .61 -1.36 (6H, m), 1 .23 (6H, m); 31 P NMR (162 MHz, DMSO-d6): delta ppm +21.7 ppm; LC-MS (Method G) 610 [M]+; RT 2.13 min

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 17702-83-9.

Reference:
Patent; NOVINTUM BIOTECHNOLOGY GMBH; SPAREY, Tim; RATCLIFFE, Andrew; STEVENSON, Brett; LAGASSE, Franz; COCHRANE, Edward; LASSALLE, Gilbert; (104 pag.)WO2018/193111; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 552330-86-6, name is 5-Bromoisoindolin-1-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 552330-86-6, Safety of 5-Bromoisoindolin-1-one

5-bromoisoindolin-1-one (1.00 g; 4.63 mmol; 1.00 eq) was dissolved in DCM (35.00 ml) then di-ferf-butyl dicarbonate (1.50 g; 6.93 mmol; 1.50 eq), triethylamine (705 pi; 5.09 mmol; 1.10 eq) and 4-dimethylaminopyridine (621.0 mg; 5.08 mmol; 1.10 eq) were added. The mixture was stirred 18h at rt, then poured onto water and extracted with DCM. The organic layer was dried over MgS04, filtered and concentrated. The residue was purified by chromatography (gradient from 100% n-heptane to 50/50 n-heptane / EtOAc) to give tert-butyl 5-bromo-1-oxo-isoindoline-2-carboxylate (1.33 g; 92 %) 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-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eng Bang Tiba; Ba Seu-ma-tin; Kon Tal-sil-bi-e; Ju Ni-en-jang—ru-i-seu; Ma Sa-reu-di-e-reu-keu-ri-seu-tin; Mon Tal-be-ti-keu-ri-seu-chan; Su Deu-an-ne; (111 pag.)KR2019/137803; (2019); A;,
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Synthetic Route of 20870-90-0, A common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, 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.

General procedure: A solution of compound 1 (0.6 mmol) and compound 2 (0.5 mmol) in 8.0 mLof alcohol 3 in the presence of 1.0 eq NaOH was stirred at reflux for 10h. After the removal of alcohol, purification by flash column chromatography (hexane/EtOAc) was carried out to furnish the corresponding products 4 as an orange solid.

The synthetic route of 20870-90-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Xiong-Li; Feng, Ting-Ting; Wang, Dan-Dan; Liu, Huan-Huan; Yang, Chao; Li, Xiao-Nian; Lin, Bing; Zhao, Zhi; Zhou, Ying; Tetrahedron Letters; vol. 57; 36; (2016); p. 4113 – 4118;,
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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. 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., name: 4-Bromoisoindoline-1,3-dione

[00287] To a solution of 4-bromoisoindole-l,3-dione 1 (226 mg, 1.0 mmol) in DMF (8 mL) was added Cs2C03 (652 mg, 2.0 mmol). The mixture was cooled to 0-5 °C and PMB-Br (302 mg, 1.5 mmol) was added dropwise. The reaction was allowed to warm to rt and stirred for 16 h. The mixture was partitioned between water and EtOAc, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water and brine, dried (Na2S04), filtered and concentrated under reduced pressure. The residue was purified (silica gel; eluting with 20percent EtOAc in hexanes) to afford compound 2 (208 mg, 74percent) as a yellow solid. 1H NMR (400 MHz, CDC13): delta 7.80 – 7.83 (m, 2H), 7.60 (m, 1H), 7.53 – 7.57 (m, 2H), 6.85 – 6.90 (m, 2H), 4.80 (s, 2H), 3.79 (s, 3H).

The synthetic route of 70478-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIDECAR THERAPEUTICS, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John. H.; (178 pag.)WO2019/70742; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1336963-95-1,Some common heterocyclic compound, 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione, molecular formula is C8H3BrFNO2, 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-Amino-4-bromo-3-fluorobenzoic acid To a solution of 6-bromo-7-fluoroindoline-2,3-dione (1.41 g, 5.80 mmol) in 2 N NaOH (15 mL) was added H2O2(30%, 3 mL) at 0 C., the mixture was stirred at 0 C. for 30 min. After stirring at rt for 16 h, the mixture was poured into ice water, the solution was acidified with Conc. HCl, the precipitate was filtered and dried in the air to afford the desired product as a white solid (1.2 g, 89% yield).

The synthetic route of 1336963-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Araxes Pharma LLC; Liu, Yi; Li, Liansheng; Ren, Pingda; (176 pag.)US2018/15087; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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.

Into a heat-vacuum dried 50 mL recovery flask, DMF (13 mL), 3-phthalimidylpropanal (manufactured by Aurora Fine Chemicals, 266.0 mg, 1.13 mmol, 1 equivalent), N,N-diallylthioacetamide (244 muL, 1.35 mmol, 1.2 equivalents), and the Cu/(S,S)-Ph-BPE solution prepared as above (100 muL, 0.10 mmol, 0.09 equivalent) were added under an argon atmosphere. The recovery flask was transferred to a constant temperature bath of -40C, and the THF solution of 2,2,5,7,8-pentamethylchromanol lithium salt prepared as above (50 muL, 0.10 mmol, 0.09 equivalent) was added, followed by stirring at -40C for 24 hours. Subsequently, a saturated aqueous solution of ammonium chloride (5 mL) and 2,2-bipyridine (15.6 mg, 0.10 mmol, 0.09 equivalent) were added, and the resulting mixture was extracted three times with ethyl acetate (5 mL). The resulting organic layer was sequentially washed with distilled water, saturated sodium bicarbonate water, and saturated brine, and then dried over anhydrous sodium sulphate. After filtration and concentration, the residue thus obtained was purified by flash column chromatography (hexane/ethyl acetate = 7/1 to 2/1 (volume ratio)) to obtain the following thioamide compound A-4 as a yellow oily matter. Yield 251.1 mg (62%, 75%ee).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(1,3-Dioxoisoindolin-2-yl)propanal, its application will become more common.

Reference:
Patent; Microbial Chemistry Research Foundation; SHIBASAKI, Masakatsu; KUMAGAI, Naoya; EP2679580; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 5394-18-3, name is 2-(4-Bromobutyl)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 5394-18-3, Computed Properties of C12H12BrNO2

General procedure: To a mixture of the corresponding R1R2NH (3.0 mmol), anhydrous K2CO3 (449 mg, 3.25 mmol) and KI (20.75 mg, 0.125 mmol) in CH3CN (12 ml) were added the appropriate intermediates 6-9 (2.5mmol). The reaction mixture was warmed to 60-65 C and stirred for 6-8 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Then water (25 mL) was added to the residue and the mixture was extracted with dichloromethane (25 mL×3). The combined organic phases were washed with saturated aqueous sodium chloride (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated to dryness under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum ether/EtOAc as eluent, obtaining the corresponding intermediates 10-13a-d.

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; Li, Yuxing; Qiang, Xiaoming; Li, Yan; Yang, Xia; Luo, Li; Xiao, Ganyuan; Cao, Zhongcheng; Tan, Zhenghuai; Deng, Yong; Bioorganic and Medicinal Chemistry Letters; vol. 26; 8; (2016); p. 2035 – 2039;,
Indoline – Wikipedia,
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