Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, 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 129487-92-9, Recommanded Product: 129487-92-9

(2) tert-butyl 5-(3,5-dichloro-phenylsulphonylamino)-2,3-dihydro-indole-1 carboxylate; Mass spectrum (ESI+): m/z = 460 [M+NH4]+

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2008/113760; (2008); A2;,
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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. 200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

A suspension of 2-borono-5-benzyloxy-indole-l-carboxylic acid tert-butyl ester Compound Id (31.2 g, 84.9 mmol), Compound Ic (12.0 g, 56.6 mmol), Pd(OAc)2 (254 mg, 1.13 mmol), DDBPP (464 mg, 1.13 mmol), K3PO4 (freshly powdered, 36.0 g, 170 mmol) and H2O (3.05 mL, 170 mmol) was stirred with an overhead mechanical stirrer for 24 hours at 25 C. The reaction mixture was diluted with H2O (1 L) and extracted with EtOAc/ THF (3/1, 3 X 300 mL). The organic extracts were dried with Na2SO4 and concentrated. The residue was purified by column chromatography (SiO2, 5-100% THF/Hex) to yield 5~benzyloxy-2-(3-oxo-2,3-dihydro-lH-isoindol-4-yl)-indole-l- carboxylic acid tert-butyl ester Compound 32 (23.2 g, 90%) as an off white solid. 1H NMR (300 MHz, CDCl3) delta 8.17 (d, J= 9 Hz, IH), 7.62-7.03 (m, HH), 6.51 (s, IH), 5.15 (s, 2 H), 4.44 (s, 2H), 1.29 (s, 9H); MS (ESI) m/z: 477 (MNa+).

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; JANSSEN PHARMACEUTICA, N.V.; WO2007/47646; (2007); A2;,
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Related Products of 21544-81-0, 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. 21544-81-0, name is 4,6-Dimethoxyindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 3,5-dimethoxyaniline (199 g, 1.30 mol) in ether (5.0 L) in a 5 L 3-necked flask was cooled to 0 C. HCl gas (227 g) was bubbled through the solution over 45 min. After 45 min at 10 C., the mixture was filtered, washed with isopropylacetate (4 L), and dried overnight on high vacuum at 45 C. to give the hydrochloride (242.3 g, 98%), as a white solid. A mixture of the hydrochloride above (20 g, 0.105 mol) and oxalyl chloride (33 mL) in a 3-necked flask equipped with a reflux condenser was heated for 2 h with stirring (170 C. external temperature), and the oxalyl chloride was distilled from the reaction mixture. The flask was cooled to 0 C. and methanol (40 mL) was added. The reaction mixture was heated to reflux for 45 min, filtered while hot, and washed with methanol (80 mL) to give the 4,6-dimethoxyisatin (17.2 g, 79%) as a yellow-green solid. To a heated solution (external temp 70 C.) of the isatin (162 g, 0.78 mol) in aqueous NaOH (40%, 1.5 L) was added H2O2 (35%, 405 mL) slowly over 2 h. After the addition of each portion of H2O2, the internal reaction temperature (initially 64 C.) increased (to a maximum temp of 80 C). After the addition was complete, the foaming reaction mixture was then stirred for an additional 2 h at 70 C., and the mixture was allowed to stir overnight while cooling to room temperature. The mixture was heated to 70 C. Additional H2O2 (75 mL) was added, and the mixture was stirred at 70 C. for a further 2 h until the reaction was complete. After cooling to 10 C. (bath temperature), aqueous Na2S2O3 (150 mL, saturated) was added. The mixture was brought to pH 8 with HCl (37%, 1.6 L) and pH 6 with acetic acid (glacial, 75 mL), without allowing the reaction mixture to warm to greater than 40 C. Filtration of the reaction mixture and washing with water (4 L) gave the expected amino acid as a tan solid (83.7 g, 55%). To a solution of the amino acid (82.7 g, 0.42 mol) in anhydrous THF (4.2 L) was added EDCl (89.2 g, 0.48 mol), HOBT (65 g, 0.48 mol), and NMM (51.3 mL), and the mixture was allowed to stir at room temperature for 3 h. Aqueous NH3 (83 mL, 50%) was added, and the mixture was stirred at room temperature for 16 h. Water (1.25 L) was added, and the mixture was extracted with DCM (2×250 mL). The combined extracts were then washed with water (2×500 mL). Concentration, formation of a slurry with ether (550 mL), filtration, and drying under high vacuum gave 2-amino-4,6-dimethoxybenzamide (46.7 g, 57%) as a brown solid.2-Amino-4,6-dimethoxy-benzamide (1.06 g, 5.4 mmol), 3,5-dimethyl-4-hydroxybenzaldehyde (0.810 g, 5.4 mmol), K2CO3 (0.747 g, 5.4 mmol) and I2 (1.645 g, 6.5 mmol) were mixed in DMF (20 mL) and the reaction mixture was heated at 80 C. for 12 h. It was cooled to room temperature and poured into crushed ice. The solid was collected and purified by column chromatography to give 2-(4-hydroxy-3,5-dimethylphenyl)-5,7-dimethoxyquinazolin-4(3H)-one (0.9 g, 51%) as a white solid. Selected data: MP 291-293 C.

The chemical industry reduces the impact on the environment during synthesis 4,6-Dimethoxyindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Wong, Norman C.W.; Tucker, Joseph E.L.; Hansen, Henrik C.; Chiacchia, Fabrizio S.; McCaffrey, David; US2008/188467; (2008); A1;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 104618-31-7, name is 2-(4-Hydroxycyclohexyl)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 104618-31-7, Recommanded Product: 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione

[00487] To a solution of PPh3 (1 .28 g, 4.9 mmol) in THF (12 mL) was added dropwise DEAD (852 mg, 4.9 mmol) at -10C. After the white solid was appeared, compound 2-(4-hydroxycyclohexyl)isoindoline-1 ,3-dione (600 mg, 2.45 mmol) was added, followed by CH3COSH (0.35 mL, 4.9 mmol) at -10C. The mixture was stirred at room temperature overnight. TLC (PE: EA = 1 :1 ) showed the reaction was complete. The mixture was poured into water (200 mL) and extracted with EtOAc (100 mL). The aqueous layer was extracted with EtOAc (100 mL X 3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo to give S-(4-(1 ,3-dioxoisoindolin-2-yl)cyclohexyl) ethanethioate (600 mg, 81 %) as a white 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, 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TOLERO PHARMACEUTICALS, INC.; XU, Yong; BRENNING, Benjamin, Gary; KULTGEN, Steven, G.; LIU, Xiaohui; SAUNDERS, Michael; HO, Koc-Kan; WO2013/13188; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, 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 201940-08-1, Computed Properties of C13H16BrNO2

0.69 ml of n-Butyl lithium (2.5M solution in hexane) was added dropwise to a stirred solution of 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (429 mg; 1.44 mmol) in anhydrous THF (10 ml) at -78 C. under an atmosphere of nitrogen. The reaction was stirred for 50 minutes then 1-methyl-4-piperidone (212 mul; 1.2 equiv.) was added and stirred at -78 C. for a further 60 minutes then warmed to room temperature. The reaction was quenched with saturated ammonium chloride solution then extracted with EtOAc. The EtOAc layer was washed with saturated NaHCO3, brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on SiO2, gradient elution from 0% to 10% 2M methanolic ammonia/DCM gave 111 mg of 5-(4-hydroxy-1-methyl-piperidin-4-yl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester as a colourless oil.

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; ASTEX THERAPEUTICS LIMITED; US2010/152184; (2010); A1;,
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Electric Literature of 104618-32-8,Some common heterocyclic compound, 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, molecular formula is C14H13NO3, 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.

4-Cyanophenyl hydrazine hydrochloride (4.41 g, 0.026 mole) was dissolved in acetic acid (100 ml) and sodium acetate (2 g) was added. 4-Phthalimido cyclohexanone (6.4 g, 0.026 mole) was added and the mixture heated under reflux overnight. The solvent was removed in vacuo and the residue triturated with methanol to give 3-phthalimido-6-cyano-1,2,3,4-tetrahydrocarbazole as a beige solid, (5.3 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Patent; SMITHKLINE BEECHAM PLC; EP603432; (1994); A1;; ; Patent; Smithkline Beecham plc; US5827871; (1998); A;; ; Patent; SmithKline Beecham P.L.C.; US5464864; (1995); A;,
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. 1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-(3-Oxocyclopentyl)isoindoline-1,3-dione

To a mixture of Compound 3 (14 g, 61 mmol) in MeOH/THF (300 mL/50mL) was added NaBH4 (3.4 g, 90 mmol) at 0 C , and stirred at rt overnight. 1 N HCl was added slowly to quenched the reaction. The mixture was concentrated in vacuo, and and the mixture was extracted with EtOAc (500 mLx3). The organic layer was concentrated to give the crude product, which was purified by column chromatography to give the compound 4 (8.0 g, 57 %). LCMS: 236.1 [M+l].

The synthetic route of 1029691-06-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVIRA THERAPEUTICS, INC.; HARTMAN, George D.; FLORES, Osvaldo A.; WO2013/96744; (2013); A1;,
Indoline – Wikipedia,
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Synthetic Route of 5181-35-1, 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 5181-35-1 as follows.

To a solution of 4-tertiary-butyl-dimethyl-silanyloxy methyl- 2H- l,2,3-triazol (40 g, 187 mmol, prepared according to the procedure described in US20150266867) in dimethylformamide (200 ml) was added potassium carbonate (28.4 g, 205 mmol) under stirring. After completion of 15 minutes of stirring a solution of 2-(2-bromoethoxy)- lH-isoindole- l,3(2H)- dione (50.5 g, 187 mmol, prepared according to the procedure described in PCT Int. Appl. 2000018790) was added. Continued stirring with continuous monitoring of the reaction. The progress of reaction was monitored by TLC (hexane: ethyl acetate, 5:5). After complete consumption of starting material the reaction mixture was filtered through celite bed to remove insolubles and filtrate was concentrated. The concentrated mass was added to water (400 ml) and extracted with ethyl acetate (2x 400 ml). The organic extracts were combined and washed with brine (200 ml), dried over anhydrous sodium sulphate. The volatiles were removed under reduced pressure yielded 67 g crude compound. The isomers were separated by column chromatography (100-200 mesh size silica gel) using hexane: ethyl acetate, 8:2 as an eluent. The non-polar isomer 2-{2-[4-(tertiary-butyl-dimethyl-silanyloxy methyl)-2H- l,2,3-triazol-2-yl]ethoxy}- lH-isoindole- l,3(2H)-dione was eluted at 12% ethyl acetate in hexane and yielded 24 g of the product. The mixture of polar isomers 2-{2-[4-(tertiary-butyl-dimethyl-silanyloxymethyl)- lH- l,2,3-triazol- l- yl]ethoxy}- lH-isoindole- l,3(2H)-dione and 2- {2-[5-(tertiary-butyl-dimethyl-silanyloxymethyl)- lH- l,2,3-triazol- l-yl]ethoxy}- lH-isoindole- l,3(2H)-dione was eluted at 45% ethyl acetate in hexane to obtain 12 g of the product.

According to the analysis of related databases, 5181-35-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
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Indoline | C8H9N – PubChem

18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, 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. Quality Control of 4,7-Dichloroindoline-2,3-dione

4,7-Dichloro-3-hydroxy-3-(2-oxo-2-(4-(pyrrolidin-l-yl)phenyl)ethyl)indolin-2-one (EXAMPLE 10): To 4,7-dichloroindoline-2,3-dione (A) (12.5 g, 0.06 mol) in 800 mL of methanol were added l-(4-(pyrrolidin-l-yl)phenyl)ethanone (B) (45 g, 0.24 mol) and 0.5 mL of diethylamine (2). The reaction was stirred at rt for 24 hours. The solvent was removed and the residue was purified with flash chromatography (0-5% Methanol/CLLCn) to get 13.5 g of brown solid. It was purified again with flash chromatography using ethyl acetate/hexane to give 11.5 g of an off white solid. Repeating the reaction at the same scale to give another 11.5 g of product. Two batches of product were combined and recrystallized from methanol to get 20.5 g as an off white solid. 4,7-Dichloro-3-hydroxy-3-(2-oxo-2-(4-(pyrrolidin-l- yl)phenyl)ethyl)indolin-2-one (EXAMPLE 10): off-white solid; 1H NMR (DMSO-d6, 400 MHz) delta 1.96 (m, 4H), 3.30 (m, 4H), 3.65 (d, 1H, J=16 Hz), 4.29(d, 1H, J=16Hz), 6.34 (s, 1H), 6.53(d, 2H, J=8Hz), 6.88(d, 1H, J=8Hz), 7.28 (d, 1H, J=8Hz), 7.72 (d, 2H, J=8Hz), 10.97(s, 1H). Chiral separation was performed on under the following conditions. Preparatory method utilized the following:a RegisCell column L: 250 mm, IS: 50 mm, particle size: 5 mum; mobile phase: methanol/CO2, ratio: 35/65, detection wavelength: 254 nm, flow rate: 325 g/min, co-solvent flow rate 113.75 ml/min. Dissolved 19.72 g in 1000 ml of methanol, for a concentration of 0.020 g/ml. The injection volume was 25.00 ml for a total amount 0.500 g/injection. Yield was (+): 9.73 g, with optical rotation +247 at 20 C and (-): 9.26 g.

The synthetic route of 18711-13-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TOKALAS, INC.; VERNIER, Jean-michael; (82 pag.)WO2016/57698; (2016); A1;,
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Electric Literature of 169037-23-4, 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.

General procedure: General method: The Schiff bases were obtained by adding an ethanolic solution of the hydrazinyl component to the solution of the keto component in equimolar amounts, refluxing the mixture in the presence of catalytic amounts of acid. If not indicated otherwise, purification was carried out by recrystallization. Carbazides were prepared by adding an equimolar amount of hydrazine to the methanolic solution of the respective isothiocyanate [53]. For the picolinylidene derivatives with ethyl group in 5-position of the pyridine moiety (2e, 2k), 5-Ethylpicolinaldehyde was prepared from 5-ethyl-2-methyl-pyridine as reported previously [13,115]. The reaction of 5-trifluoromethoxyisatin (50mg, 0.22mmol) with N-(4-methoxyphenyl)hydrazinecarbothioamide C-1 (43mg, 0.22mmol) in ethanolic solution under HCl-catalysis resulted in a yellow fluffy precipitate, which was identified as the product in 70% yield (65.7mg, 0.16mmol). 1H NMR (500MHz, DMSO-d6): delta=12.60 (s, 1H), 11.36 (s, 1H), 10.78 (s, 1H), 7.78 (s, 1H), 7.49-7.41 (m, 2H), 7.41-7.31 (m, 1H), 7.02 (d, 1H, 3J(H,H)=5.0Hz), 7.01-6.95 (m, 2H), 3.78 (s, 3H). 13C NMR (126MHz, DMSO-d6): delta=176.6, 162.7, 157.5, 143.5, 141.2, 131.1, 130.9, 127.3 (2C), 124.0, 121.5, 120.7 (d {121.19, 119.15}, 1J(C,F)=255.7Hz), 114.4 (2C), 113.6, 112.1, 55.3. Anal. Calcd. for C17H13N4SO3F3: C: 49.76; H: 3.19; N: 13.65. Found: C: 49.61; H: 3.477; N: 13.53

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; Pape, Veronika F.S.; Toth, Szilard; Fueredi, Andras; Szebenyi, Kornelia; Lovrics, Anna; Szabo, Pal; Wiese, Michael; Szakacs, Gergely; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 335 – 354;,
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