Tag: M.W=200-300

These common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-2-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. Recommanded Product: 5-Bromoindolin-2-one

Starting Material 7: (Z)-5-Bromo-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one A mixture of 5-bromo-1,3-dihydro-2H-indol-2-one (3.10 g, 14.62 mmol) (Starting Material 6) and pyrrole-2-carboxaldehyde (1.46 g, 15.35 mmol) (Aldrich) in 2-propanol (73 mL) was treated with 10-12 drops of piperidne. The reaction mixture was heated at reflux for 20 h and then allowed to cool to 23 C., at which time, the reaction mixture was filtered. The resulting solid was washed well with hexanes, followed by petroleum ether, and then allowed to air dry to provide pure (Z)-5-bromo-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one as a yellow solid which was used without further purification. (Yield 4.01 g, 95%; mp 267-268 C.).

The synthetic route of 5-Bromoindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; US6313310; (2001); B1;,
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Synthetic Route 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.

(cis) 1-(1 /-/-Benzimidazol-2-ylmethyl)-1 ,2,3,4,4a,5,6,10b-octahydro-1 ,10- phenanthroline (0.045 g, 0.14 mmol), 2-(5-bromopentyl)-1 /-/-isoindole-1 ,3(2H)-dione (0.062 g, 0.21 mmol), potassium iodide (5 mg), and N,N-diisopropylethylamine (0.050 g, 0.31 mmol) in 3 mL of dimethylformamide were heated to 80 9C for 16 hours. The mixture was allowed to cool to room temperature and hydrazine (0.4 mL, 14.0 mmol) was added. The mixture stirred at room temperature overnight. The mixture was quenched with water and extracted 3 times with ethyl ether. The ether layers were combined, dried over sodium sulfate, and concentrated. The residue was purified by silica chromatography eluting with a 0% to 10% gradient of 30% aqueous ammonium hydroxide in acetonitrile to yield 0.01O g (18%) of (cis)-5-[2-(3,4,4a,5,6,10b- hexahydro-1 ,10-phenanthrolin-1 (2/-/)-ylmethyl)-1 H-benzimidazol-1-yl]-1- pentanamine. 1H NMR (400 MHz, METHANOL-D4) delta ppm 1.0 (m, 2 H), 1.3 (m, 3 EPO H), 1.4 (s, 2 H), 1.6 (m, 1 H), 1.7 (m, 2 H)1 2.1 (m, 1 H), 2.3 (m, 2 H), 2.5 (m, 3 H), 2.8 (m, 1 H), 2.9 (m, 1 H), 3.1 (m, 1 H), 3.4 (s, 1 H), 3.5 (d, J=13.9 Hz, 1 H), 3.9 (m, 1 H), 4.1 (m, 1 H), 4.2 (d, J=13.9 Hz, 1 H), 7.2 (m, 2 H), 7.3 (m, 2 H), 7.5 (d, J=7.1 Hz, 1 H), 7.7 (d, J=7.9 Hz, 1 H), 8.4 (s, 1 H); MS m/z404 (M+1).

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; SMITHKLINE BEECHAM CORPORATION; WO2006/96444; (2006); A2;,
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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. 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-(2-Oxopropyl)isoindoline-1,3-dione

Example 491; N-[7-(3-Fluoro-benzenesulfonyl)-1-methyl-1 ,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmeth isobutyramideStep 1 :2-(7-lodo-1-methyl-1 ,2,3,4-tetrahydro-benzofuro[2,3-c]pyridin-1-ylmethyl)- isoindole-1 ,3-dione To a mixture of 2-(6-iodo-benzofuran-3-yl)-ethylamine (2.00 g, 6.97 mmol) and 2-(2-oxo-propyl)- isoindole-1 ,3-dione (4.25 g, 20.9 mmol) was added trifluoroacetic acid (8.00 mL, 104 mmol) and then heated at 80 C . After 16 h, additional ketone (3 eq) was added and heating continued. After a total of 3 days, the reaction mixture was basified (DCM-aq. NaHC03) and the resulting precipitate was filtered, rinsed with DCM and dried to give an off-white solid, mp 302-304 C dec; MS m/z 473 [M + H]+.

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CEPHALON, INC.; BACON, Edward R.; BAILEY, Thomas R.; DUNN, Derek D.; HOSTETLER, Greg A.; MCHUGH, Robert J.; MORTON, George C.; ROSSE, Gerard C.; SALVINO, Joseph M.; SUNDAR, Babu G.; TRIPATHY, Rabindranath; WO2011/87712; (2011); A2;,
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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 118289-55-7 as follows. category: indolines-derivatives

Example 1; Methylene chloride (200 ml) is added to 1-(1 ,2-Benzisothiazol-3- yl)piperazine (15 gm), stirred for 10 minutes and then triethylamine (22 ml) is added drop wise for 10 minutes. Trimethylsilyl chloride (15 ml) is added drop wise to the reaction mass for 20 minutes, tetrabutyl ammonium bromide (5 gm) is added and stirred for 1 hour at 25-300C. Then the reaction mass is heated to 400C and methylene chloride is distilled under vacuum. To this reaction mass sodium carbonate (16 gm) and 5-(2-chloroethyl)-6-chloro-oxindole (16 gm) are added, stirred for 10 minutes and added water (400 ml) and sodium iodide (2 gm). The contents are heated to 1000C and stirred for 7 hours 30 minutes at 95 – 1000C. Solid is filtered and slurried in 200 ml of water, filtered and washed with water (100 ml). Then the solid is slurried in isopropyl alcohol (75 ml) at reflux, refluxed for 1 hour and then filtered the solid at reflux point to give 15 gm of ziprasidone (HPLC purity: 98.36%).

According to the analysis of related databases, 118289-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HETERO DRUGS LIMITED; WO2006/80025; (2006); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, 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 6326-79-0, SDS of cas: 6326-79-0

To a solution of 3a (150 mg, 0.66 mmol) in dry acetone (30 mL) was added Na2CO3 (anh. ) (1.0 g) and dimethylsulfate (0.8 mL) under Ar and the reaction mixture was heated at 60 C for 20 h. Then, the mixture was filtered and the filtrate was carefully evaporated using a high vacuum pump (under 40 C). The solid residue was submitted to flash chromatography with CH2C12 to afford lla (140 mg, 0.58 mmol, 85%) (see Scheme 2 in Fig. 2B).

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; THE ROCKEFELLER UNIVERSITY; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; WO2005/41954; (2005); A1;,
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Related Products of 104618-32-8, 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 104618-32-8 as follows.

Hydrochloric acid (35%) (3.2 L) was added to a cooled solution of 4-aminobenzamide (2.0 Kg, 14.69 mol) in water (14 L, 7 volumes) at 5-100C. Then p-toluene sulphonic acid (10.1 Kg, 3.44 mol) was added to the reaction mixture and further cooled to -5C to -100C. Sodium nitrite (1.76 Kg, 25.7 mol) was dissolved into water (4 L, 2 volumes) and added to the cooled reaction mixture over a period of 2.5 hours at -5C to -100C and further stirred for 4 hours. Sodium sulphite (5.6 Kg, 44.4 mol) was dissolved into water (16 L, 8 volumes) and added dropwise to the diazonium salt over a period of 3 hours at a temperature of -5C to -100C. After stirring for 2 hours, the temperature of the reaction mixture was allowed to rise to ambient and stirred for 12 hours. The reaction was monitored by TLC. Methanol (16 L, 8 volumes) was added to the yellow suspension and 4-phthalimido- cyclohexanone (4.64 Kg, 19.07 mol) was added portionwise at a temperature of 40-450C. After maintaining the reaction mixture at 40-450C for 30 minutes, the temperature of the reaction mixture was raised to 70-750C and maintained for 8 hours. After completion of the reaction, the mixture was cooled to 25-300C, filtered and washed with water (40 L). The wet cake was mixed with water (40 L) and the pH adjusted to 7-8 using 10% potassium carbonate (aq) solution, and the slurry was filtered and washed with water (40 L). The product was dried under vacuum at 60-650C. The crude product was purified by reflux in dichloromethane (30 L) and dried to afford the title compound (3.70 Kg). Molar yield: 70%HPLC purity: 98.06%

According to the analysis of related databases, 104618-32-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENERICS [UK] LIMITED; MYLAN INDIA PRIVATE LIMITED; GORE, Vinayak Govind; GADKAR, Maheshkumar; TRIPATHI, Anilkumar; MANKAR, Viraj; WO2010/122343; (2010); 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. 106976-23-2, name is 5-Bromo-6-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 106976-23-2

A 30% hydrogen peroxide sol. (2 mL/g) was added to a sol. of isatin derivative in 10 M of sodium hydroxide sol. (10 mL/g) at 70 C. and the reaction mixture was then held at this temperature for 1 h. The mixture was then cooled to 0 C., adjusted to pH 8 with conc. HCl, diluted with EE and then brought to pH 4-5. The organic phase was washed with water, dried (NaSO4) and the solvent removed. (Yield approx. 60%)

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; Gruenenthal GmbH; US2009/69320; (2009); 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 169037-23-4 as follows. Computed Properties of C9H4F3NO3

Diethylcyanomethylphosphonate (279 mg, 1.58 mmol) was dissolved in dry THF (6 mL) at 0oC. Sodium hydride (66 mg, 1.15 mmol) was added and, to the resulting suspension, 5-trifluoromethoxyistain (347 mg, 1.50 mmol) was added slowly. Upon completion of the reaction as shown by TLC analysis, water (10 mL), brine (10 mL) and ethyl acetate (10 mL) were added and the aqueous layer extracted with ethyl acetate (3 x 5 mL) and dried with Na2SO4. The solvent was evaporated in vacuo and the resulting solid was purified by column chromatography (PSp:EtOAc 1:0 to 1:1) to yield a yellow product (31%), 1H NMR (400 MHz, CDCl3): d 6.39 (s, 1H), 6.91 (d, J 8.7, 1H), 7.26-7.31 (m, 1H), 7.84 (br s, 1H), 7.94 (d, J 1.9, 1H); 13C NMR (100 MHz, CDCl3): d 99.8, 111.3, 115.3, 118.9, 120.43 (q, J 258), 120.6, 126.9, 141.3, 142.5, 144.8 (q, J 2.1), 165.9; IR (neat, cm-1): 3254, 2228, 1760, 1728, 1624, 1473, 1245, 1124; HRMS: m/z: [M+Na]+ calcd for C11H5N2O2F3Na, 277.0195; found, 277.0188.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Davis, Holly J.; Kavanagh, Madeline E.; Balan, Tudor; Abell, Chris; Coyne, Anthony G.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3735 – 3740;,
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Application of 118289-55-7, These common heterocyclic compound, 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-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.

General procedure: Equimolar mixture of 6-chloro-5-(2-chloroethyl)-1,3-dihydro-2H-indol-2-one 1 (1.00mol) and the carbonyl compound (4i-x) (1.00mol) was stirred at RT in methanol (10mL) for 2h in presence of potassium carbonate (1.20mol). After completion, the reaction mass was filtered to remove inorganic salt, added methanol (10-20mL) and activated charcoal to the filtrate and stirred for 1hr. The crude product was filtered to remove charcoal, methanol was evaporated and cooled to 0-5C to get crude solid. Recrystallized using aqueous ethanol or methanol (Yield 60-70%).

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Meti, Gangadhar Y.; Kamble, Atulkumar A.; Kamble, Ravindra R.; Somagond, Shilpa M.; Devarajegowda; Kumari, Sandhya; Kalthur, Guruprasad; Adiga, Satish K.; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 221 – 231;,
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Reference of 6326-79-0, 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. 6326-79-0, name is 6-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2·NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

The chemical industry reduces the impact on the environment during synthesis 6-Bromoisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
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