Tag: M.W=200-300

These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, 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. Formula: C8H6BrNO

5-Bromoisoindolin-l-one (15 g, 70.74 mmol) and sodium methyl mercaptide (12.40 g,176.85 mmol) were mixed together in DMF (150 mL) and heated to 100 C for lh. The reaction mixture was cooled to room temperature and poured into water (160 mL), and the aqueous phase was extracted with EtOAc (400 mL). The layers were then separated and the aqueous phase extracted with EtOAc (3 x 200 mL). The combined organic extracts were washed with brine (3 x 100 mL), dried using a phase separator cartridge and concentrated in vacuo. 5-(Methylthio)isoindolin-1-one (12.00 g, 95%) was obtained as a yellow solid. The material was used in the next step without further purification. LC/MS: m/zrrl8O [M+H]. ?H NMR (500 MHz, DMSO-d6) i5 2.54 (s, 3H), 4.33 (s, 2H), 7.33 (d, 1H), 7.44 (s, 1H), 7.56 (d, 1H), 8.43 (s, 1H).

The synthetic route of 5-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; LEVER, Sarah; NARJES, Frank; OLSSON, Roine, Ingemar; VON BERG, Stefan; (124 pag.)WO2018/229155; (2018); A1;,
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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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Computed Properties of C9H6BrNO2

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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Application of 2058-72-2, 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: At the first, a mixture containing (10% mol) aimin base ligand and transition metal salts (10% mol) was prepared in 10 ml dichloromethan. Then a mixture of isatin derivatives (1 mmol) and (S)-proline (1.1 mmol), in 10 mL ethanol was added to mixture. After completion of the reaction (monitored by TLC), the reaction mixture was extracted with dichloromethane (15 mL). The combined organic layer dried over anhydrous MgSO4. The organic layer was concentrated in vacuum to furnish the products, which were recrystallized from ethanol.

The synthetic route of 5-Bromo-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Taghizadeh, Mohammad Javad; Javidan, Abdollah; Jadidi, Khosrow; Journal of the Korean Chemical Society; vol. 59; 3; (2015); p. 205 – 208;,
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Synthetic Route of 2058-72-2, 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 2058-72-2 as follows.

General procedure: Isatin (10 mmol), 2,2,2-trifluoroethylamine hydrochloride (15 mmol) and p-toluenesulfonic acid (0.5mmol) were suspended in toluene (10 mL) in a two-neck flask with a water separator and a condenser.The mixture was then heated to separate the water until complete disappearance of the starting materials.After cooling to room temperature, the mixture was washed with a small quantity of saturated NaHCO3solution and dried by Na2SO4, After evaporation of the organic solvent, the crude residue was purified byflash chromatography (silica gel, hexane/EtOAc) and afforded the resulting ketimine.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Huang, Wei-Jie; Chen, Qing; Zhu, Wen-Run; Lin, Ning; Long, Xian-Wen; Pan, Wei-Gao; Weng, Jiang; Lu, Gui; Heterocycles; vol. 94; 5; (2017); p. 879 – 893;,
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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;,
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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;,
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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;,
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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;,
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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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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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