Tag: M.W=200-300

Adding some certain compound to certain chemical reactions, such as: 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, 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 15362-40-0. 15362-40-0

General procedure: Compounds 4-9 were prepared through knoevenagel condensation of compounds 12 and 13 (1 mmol) with active methylene compounds including 1-(3-chlorophenyl)-3-methyl-2-pyrazolin-5-one, oxindole and indolinone (1 mmol). The reactants were heated at 160-180 C for about 10-20 min in oil bath and the completion of the reaction was monitored using TLC. The crude products were solidified by triturating with diethyl ether and purified by recrystallization and column chromatography.

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 1-(2,6-Dichlorophenyl)-2-indolinone.

Reference:
Article; Singh, Palwinder; Shaveta; Sharma, Surbhi; Bhatti, Rajbir; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 77 – 82;,
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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. 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. 2058-72-2

General procedure: A mixture of substituted isatin 4a-v (1 mmol), sarcosine 5 (1 mmol) and 3-(1H-indol-3-yl)-3-oxo-2-(2-oxoindolin-3-ylidene)propanenitrile 6 (1 mmol) were refluxed in ethanol (5 mL). After completion of the reaction as evidenced by TLC analysis, the reaction mixture was poured into ice-water, the resulting solid was filtered off and purified by column chromatography using ethyl acetate/petroleum ether (6:4) as an eluent to afford pure spirooxindoles 7a-v.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arun; Bhaskar; Balachandran; Ignacimuthu; Perumal; Bioorganic and Medicinal Chemistry Letters; vol. 23; 6; (2013); p. 1839 – 1845;,
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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. 923590-95-8

Step a To a stirred solution of 4-bromoisoindoline hydrochloride (CAS Number 923590-95-8; 0.1 g, 0.426 mmol) in l,4-dioxane:water (5: 1; 6 ml) were added phenylboronic acid (0.078 g, 0.64 mmol) and K2C03 (0.176 g, 1.279 mmol) at rt. The reaction mixture was degassed with nitrogen for 10 min. Pd(PPh3)4 (0.024 g, 0.021 mmol) was added to the reaction and reaction mixture was heated at 100C for 16 h. The resulting reaction mixture was cooled to rt and combined with 2 other batches prepared on the same scale by an identical method. The reaction mixture was poured into water (100 ml) and extracted with EtOAc (2 x 20 ml). The combined organic phase was separated, dried over Na2S04, filtered and evaporated to dryness. The residue was re-dissolved in EtOAc (2 ml) and 4M HC1 in 1,4- dioxane (0.3 ml) was added at 0C. The mixture was stirred at rt for 30 min. The excess of solvent was distilled under vaccum and residue was triturated with diethyl ether (10 ml) and EtOAc (10 ml) yielding 4-phenylisoindoline hydrochloride (0.1 g, 0.512 mmol). This material was used for the next step without further purification. LCMS: Method A, 1.731 min, MS: ES+ 196.44; NMR (400 MHz, DMSO-d6) delta ppm 9.84 (br, s, 1H), 7.42 – 7.60 (m, 8 H), 4.49 – 4.63 (m, 4 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 923590-95-8, its application will become more common.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
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99365-40-9, These common heterocyclic compound, 99365-40-9, name is 6-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.

a) 6-(4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2- l)-1 ,3-dihydro-indol-2-one6-Bromo-1 ,3-dihydro-2H-indol-2-one (150 mg, 0.71 mmol), bis(pinacolato)diboron (233 mg, 0.92 mmol), KOAc (104 mg, 1.07 mmol) and Pd(dppf)CI2 (29 mg) in anhydrous DMF (3 mL) were heated under N2 at 90C for 16 h. The mixture was diluted with EtOAc (40 mL) and washed with water (30 mL) then brine (30 mL). The organic layer was dried (Na2S04) and concentrated in vacuo. Purification by column chromatography (MeOH-DCM gradient) gave a yellow solid (72 mg, 39%); 1H NMR (400 MHz, DMSO-d6) delta 10.38 (s, 1 H), 7.27 (dd, J=7.3, 0.9 Hz, 1 H), 7.23 (d, J=7.3 Hz, 1 H), 7.07 (s, 1 H), 3.49 (s, 2H), 1.29 (s, 12H); m/z (ES+APCI)+: 260 [M+H]+.

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 99365-40-9.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; LARGE, Jonathan; BOULOC, Nathalie; WALLACE, Claire; WO2011/101640; (2011); A1;,
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Adding some certain compound to certain chemical reactions, such as: 99365-40-9, name is 6-Bromoindolin-2-one, 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 99365-40-9. 99365-40-9

Example 20: 3-Amino-6- (4-12-hydroxy-2- [5- (2-oxo-2, 3-dihydro-lH-indol-6-yl)- pyridin-2-yl]-ethylamino}-piperidin-1-yl)-4-trifluoromethyl-thieno [2, 3-b] pyridine-2- carboxylic acid amide An N2-purged suspension of 3-Amino-6-{4-[2-(5-bromo-pyridin-2-yl)-2-hydroxy- ethylamino]-piperidin-1-yl}-4-trifluoromethyl-thieno [2, 3-b] pyridine-2-carboxylic acid amide (150 mg, 0.268 mmol), bis (pinacolato) diboron (153 mg, 0.590 mmol), [1,1′- bis (diphenylphosphino) ferrocene] dichloropalladium (II)-CH2Cl2 complex (33 mg, 0.040 mmol), and potassium acetate (133 mg, 1.34 mmol) in dry DMF (4 ml) was heated at 80 C for 2.5 h. The crude reaction mixture was then added directly via syringe to a stirring, N2- purged suspension of 6-bromo-2-oxindole (65 mg, 0.295 mmol), tetrakis (triphenylphosphine) palladium (0) (47 mg, 0.040 mmol), and potassium carbonate (74 mg, 0.536 mmol) in dry DMF (6 ml) and water (2 ml) at rt. The sealed mixture was heated to 85 C for 4 h. The crude reaction was applied direcly to a Si02 column and purified (0-25% MeOH/CH2Cl2 with NH4OH). Fractions containing desired product were pooled and concentrated. The yellow residue was dissolved in 2 ml DMF and applied to a 2 mm prep plate (Merck) eluting with 10% MeOH/CH2Cl2 with 1% NH40H. The yellow product crystallized at the origin and the impurities were removed by being carried up the plate. The recovered yellow residue was dissolved in 1 ml DMF, 2 ml MeOH, 5 ml EtOAc, and 5 ml CH2C12 and crystallized by the addition of 30 ml hexanes to give 20.5 mg, 11.9% of 3-Amino-6- (4-f2-hydroxy-2- [5- (2-oxo-2, 3-dihydro-lH-indol-6-yl)-pyridin-2-yl]- ethylamino}-piperidin-l-yl)-4-trifluoromethyl-thieno [2, 3-b] pyridine-2-carboxylic acid amide product. ES+ 612. 4 m/z (MH+).

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 6-Bromoindolin-2-one.

Reference:
Patent; BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.; WO2005/56562; (2005); A1;,
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104618-32-8, Name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, 104618-32-8, belongs to indolines-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

EXAMPLE 3 3-Amino-6-methoxy-1,2,3,4-tetrahydrocarbazole hydrochloride Reaction of 4-methoxyphenyl hydrazine hydrochloride (0.87 g, 5.0 mmol) with 4-phthalimido-cyclohexanone (1.22 g, 5.0 mmol) in ethanol (20 ml) heated under reflux for 2 hr, followed by cooling and removal of the precipitated solid by filtration gave 3-phthalimido-6-methoxy-1,2,3,4-tetrahydrocarbazole (1.62 g).

Statistics shows that 2-(4-Oxocyclohexyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 104618-32-8.

Reference:
Patent; SmithKline Beecham P.L.C.; US5464864; (1995); A;,
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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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., 118289-55-7

2. Preparation of ZPR in glycerol In a three necked flask was charged BITP HC1 (25g, 0. 098 mol), glycerol (62 ml), Na2C03 (13g) and the mixture was stirred for 10 minutes. CEI (5.9g) was added and the reaction mixture was heated for 3h at 115-120C. After 3h, the reaction was almost complete; after cooling to room temperature the solid was filtrated and was triturated in water and dried. The dried solid weights 42 g and the purity was 89.03%.

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; TEVA PHARMACEUTICAL INDUSTRIES LTD.; TEVA PHARMACEUTICALS USA, INC.; WO2005/40160; (2005); A2;,
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A common compound: 4403-36-5, name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, belongs to indolines-derivatives compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 4403-36-5

To a solution of 2-{3-exo-[(R)-1-((S)-2-methyl-propane-2-sulfinylamino)-2-(2,4,5-trifluoro- phenyO-ethylJ-beta-aza-bicyclop^.ijoctane-beta-sulfonylJ-ethylamine (100 mg, 0.202 mmol) in dichloromethane / 2N NaOH (2 mL, 1/1) are 2-phtalimidoethanesulfonyl chloride (167 mg, 0.605 mmol). The resulting solution is stirred at 500C during 2h before extraction and evaporation of organic phase to yield the crude compound. It is purified by preparative HPLC (Column Waters C18 ODB 5mum 19×50, Gradient: 0-2.5 min 5% ACN, 2.5-12.5 min 5-100% ACN, 12.5-15 min 100% ACN) to yield title compound. MS: 734 [M+H]+HPLC (Zorbax SB C18, 2min method (0-0.8min 10-95%ACN, 0.8-1.5min 95%ACN, 1.5- 1.6min 95-10%ACN, 1.6-2min 10%ACN): 1.43 min.

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, 4403-36-5, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/115821; (2007); 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. 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. 2058-72-2

General procedure: Triethanolamine (20 mol %) wasadded to a solution of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide(1) (0.198 g, 0.001 mol), malononitrile (2) (0.066 g,0.001 mol), and appropriate isatin 3a-n (0.001 mol) in EtOH (5-10 ml). The mixture was refluxed for 1 h. The obtained precipitates of compounds 4a-n were filtered off,washed with EtOH, dried in air, and recrystallized from EtOH-DMF, 1:1.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Grygoriv, Galina V.; Lega, Dmitry A.; Zaprutko, Lucjusz; Gzella, Andrzej K.; Wieczorek-Dziurla, Ewa; Chernykh, Valentine P.; Shemchuk, Leonid A.; Chemistry of Heterocyclic Compounds; vol. 55; 3; (2019); p. 254 – 260;,
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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. 99365-40-9, name is 6-Bromoindolin-2-one, A new synthetic method of this compound is introduced below., 99365-40-9

Sodium hydride (4.53 g, 94.3 mmol, Eq: 4) and dry tetrahydrofuran (20 ml) were mixed under argon. A suspension of 6-bromoindolin-2-one (5 g, 23.6 mmol, Eq: 1.00) in dry tetrahydrofuran (50 ml) was added in portions. The mixture was stirred at room temperature for 20 min. Then iodomethane (13.4 g, 5.87 ml, 94.3 mmol, Eq: 4) was added dropwise at 23-26 C. The light brown suspension was stirred at room temperature overnight. The reaction mixture was carefully quenched with 10 ml of saturated ammonium chloride. The mixture was diluted with 200 ml of ethyl acetate, 100 ml of water and 50 ml of saturated sodium bicarbonate. The mixture was extracted with 100 ml of ethyl acetate (2x) and the organic layers were washed with 50 ml of saturated sodium bicarbonate. The combined organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel to afford the desired product a white solid (4.16g, 69 %). MS (m/z) = 254.4/256.4 [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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GAUFRETEAU, Delphine; KOLCZEWSKI, Sabine; PLANCHER, Jean-Marc; STOLL, Theodor; (99 pag.)WO2017/76842; (2017); A1;,
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