Category: indolines-derivatives

Reference of 923590-95-8,Some common heterocyclic compound, 923590-95-8, name is 4-Bromoisoindoline hydrochloride, molecular formula is C8H9BrClN, 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.

Adding a sodium hydroxide solution to the solution containing Compound I, And extracted with dichloromethane, Add Boc 2 O dropwise, react overnight, add water, separate dichloromethane, wash twice with saturated sodium chloride, dry over anhydrous sodium sulfate, concentrate, separate and purify by column chromatography, use 100-200 mesh silica gel column, wash Deionization using PE (petroleum ether): EA (ethyl acetate) = 40:1-20:1, to give an off-white solid 45g.

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Xiaozhuang College; Shanghai Weifenqi Pharmaceutical Technology Co., Ltd.; Zhu Yuan; Wu Longzhong; Li Jianxiang; Yuan Yanfen; (11 pag.)CN109678787; (2019); A;,
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Application 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.

Step A: Preparation of 2-{(S)-1-[5-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)pentyl]pyrrolidin-3-yl}-2,2-diphenylacetamide A 200-mL three-necked flask was charged with 2,2-diphenyl-2-(S)-pyrrolidin-3-ylacetamide, the intermediate from Example A (2.8 g, 10 mmol), N-(5-bromo-pentyl)phthalimide (3.55 g, 12 mmol), triethylamine (4.27 mL, 30 mmol) and ACN (100 mL). The reaction mixture was stirred at 55 C. for 8 hours and then concentrated under reduced pressure. IPAc was added to the residue and this mixture was washed with 0.5 N NaOH (2*100 mL), brine (1*100 mL), dried over magnesium sulfate, filtered and concentrated to give 5 g of the title intermediate (100% yield). MS m/z [M+H+] calc’d for C31H33N3O3 496.3; found 496.4.

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; Theravance, Inc.; US2005/203161; (2005); A1;,
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Application of 59-48-3, A common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

EXAMPLE I 5-acetyl-2-indolinone 171 g (1.28 mol) aluminium chloride in 500 ml 1,2-dichloroethane are cooled in the ice bath. Then 78 g (1.1 mol) acetylchloride are added dropwise, so that the temperature does not exceed 10 C. After 1 h, 71.3 g (0.53 mol) 2-indolinone (1,3-dihydro-indol-2-one) are added in 4 batches and the temperature is kept at 10-12 C. The reaction mixture is left overnight to warm up slowly to ambient temperature. Then the solution is slowly added to 1 kg ice with vigorous stirring. The slurry is diluted with 1 l water and stirred for another 30 min. Then the precipitate is suction filtered. Yield: 80.9 g (86.3% of theory) Rf=0.36 (silica gel, ethyl acetate/cyclohexane/methanol 9:9:2) C10HgNO2 (MG=175.19) Mass spectrum: m/z=174 (M-H)-

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; Boehringer Ingelheim International GmbH; US2005/234120; (2005); A1;,
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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 5332-26-3 as follows. Recommanded Product: 5332-26-3

Methyl 3-(1 ,3-dioxoisoindolin-2-yl)-2-(4-(triisopropylsilyloxy)phenyl) propanoate (E3) was prepared from E2 according to the below:To a solution of LiHMDS in THF cooled to -78C was added a cooled solution (approx – 78C) of methyl-2-(4-(triisopropylsilyloxy) phenyl)acetate (E2) in THF via syringe. The solution was stirred at -78C for 30 min. Bromo-methyl phthalimide was added directly to the anion, and the solution was immediately removed from the -78C bath and placed in an ice bath and stirred for 2 h. The reaction was then poured into NH4CI(sat) and extracted with EtOAc. The organics were dried (Na2SO4), filtered, and evaporated. Column chromatography 0-20% EtOAc/Hexanes gave pure methyl 3-(1 ,3-dioxoisoindolin-2-yl)-2-(4- (triisopropylsilyloxy)phenyl)propanoate (E3).

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AERIE PHARMACEUTICALS, INC.; DELONG, Mitchell, A.; STURDIVANT, Jill, Marie; ROYALTY, Susan, M.; HEINTZELMAN, Geoffrey, Richard; YINGLING, Jeffrey, D.; KOPCZYNSKI, Casey; WO2010/127329; (2010); A1;,
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Related Products of 39603-24-2,Some common heterocyclic compound, 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione, molecular formula is C10H9NO2, 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.

j0309j A. 6,8-Dimethyl-2-(3-methyl-1-benzofuran-2-yl)quinoline-4-carboxylic acid. To a100 ml. round-bottom flask was placed a solution of 1-(3-methyl-1-benzofuran-2-yl)ethan-1-one (1 g,5.74 mmol) in EtOH (20 mL) then 5,7-dimethyl-2,3-d1H ydro-1H -indole-2,3-dione(800 mg,4.57 mmol) and KOH (800 mg) were added. The resulting solution was heated to80C and stirred for 16 h. The reaction was cooled to rt and concentrated under reducedpressure. The residue was dissolved in 100 mL of H20,washed with MTBE (3×50 mL),and the pH of the solution was adjusted to 2-3 with 2N HC1. The resulting precipitate was isolated by filtration and washed with MeOH (3×50 mL) affording 485 mg (32%) of the title compound as a yellow solid. Mass Spectrum (LCMS,ESI pos): Calcd. for C2,H,8NO3: 332.1 (M+H); Found: 332.0. 1H NMR (300 MHz,DMSO-d6): oe 13.95 (s,1H ),8.43 (s,1H ),8.33 (s,1H ),7.80-7.77 (d,J= 7.5 Hz,1H ),7.73-7.70 (d,J= 8.1H z,1H ),7.61 (s,1H ),7.47-7.42 (t,J= 7.5 Hz,1H ),7.38-7.33 (t,J= 7.5 Hz,1H ),2.85 (s,3H),2.73 (s,3H),2.52 (s,3H). HPLC purity(254 nm): 99.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,7-Dimethylindoline-2,3-dione, its application will become more common.

Reference:
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (2017); A1;,
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Electric Literature of 147149-84-6, A common heterocyclic compound, 147149-84-6, name is 4-Bromo-5-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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.

Hydrogen peroxide (40 ml, 391.60 mmol) was added to a solution of 4-bromo-5-methyl-1H-indole-2,3-dione (20 g, 83.31 mmol) in 2M NaOH (400 ml) at rt. The resulting solution was stirred at rt for 2 h. Sodium sulfite (48 g) was then added and the mixture was stirred for another 0.5 h at rt. The reaction mixture was extracted with EtOAc (200 mL) and the aqueous layer pH adjusted to pH 4 with concentrated HCl. A precipitate was collected by filtration, washed with water (300 ml) and dried under vacuum to afford 6-amino-2-bromo-3-methylbenzoic acid (12.4 g, 65%) as a pale yellow solid; 1H NMR (400 MHz, MeOD, 30 C.) 2.29 (3H, s), 6.70 (1H, d), 7.07 (1H, d); m/z: ES+ [M+H]+=230.

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; ASTRAZENECA AB; Kettle, Jason Grant; Bagal, Sharanjeet; Robb, Graeme Richard; Smith, James Michael; Goldberg, Frederick Woolf; Cassar, Doyle Joseph; Feron, James Lyman; US2019/177338; (2019); A1;,
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Reference of 17564-64-6, These common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, 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 initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.53 2-((2-(2-(Propan-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (1C) Yellow powder, mp 119-124 C, 99% yield; 1H NMR (400 MHz, DMSO-d6): delta 1.79 (s, 3H, CH3), 1.88 (s, 3H, CH3), 3.95 (s, 2H, CH2, thiazolidinone), 5.52 (s, 2H, ArCH2), 7.73-8.31 (m, 4H, Ar).

Statistics shows that 2-(Chloromethyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 17564-64-6.

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
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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;,
Indoline – Wikipedia,
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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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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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H7NO

5-Acetyl-2-oxindole 2-Oxindole (3 g) was suspended in 1,2-dichloroethane and 3.2 mL acetyl chloride were slowly added. The resulting suspension was heated to 50 C. for 5 hours, cooled, and poured into water. The resulting precipitate was collected by vacuum filtration, washed copiously with water and dried under vacuum to give 2.9 g (73% yield) of the title compound as a brown solid.

The synthetic route of 59-48-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
Indoline – Wikipedia,
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