Tag: M.W=200-300

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. 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of tert-Butyl 5-aminoindoline-1-carboxylate

To a solution of 300mg (1.28mmol) of the compound obtained in the Manufacturing Example 2 in 10mL of anhydrous dichloromethane were added 191muL (2.69mmol) of acetyl chloride and 375muL (2.69mmol) of triethylamine, and the mixture was stirred for 1 hour at room temperature. Then, water was added to the reaction mixture and the mixture was extracted with dichloromethane. The organic layer was dried over with anhydrous sodium sulfate and removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 1/1 to 1/2) to give 370mg (quantitative) of the title compound.

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 129487-92-9.

Reference:
Patent; Daiichi Asubio Pharma Co., Ltd.; EP1775298; (2007); A1;,
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These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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. COA of Formula: C8H4BrNO2

General procedure: 4-Bromoisatin (1 eq) was added to a solution of the potassium trifluoroborate salt (1.4 eq), K3P04 (3.6 eq) and degassed solvent. The reaction mixture was degassed and Pd(PPh3)2C12or Pd(dppf)2C12 (0.1 eq) was added. The reaction vessel was sealed and heated by microwave irradiation (Biotage Initiator) for 4 h at 130¡ãC. The reaction mixture was cooled to rt, diluted with EtOAc (-10 mL/mmol substrate) and filtered through Celite?. The organic solution was washed with brine (-10 mL/mmol substrate) and the resulting aqueous layer was further extracted with EtOAc (2 x). The combined organic layers were dried over MgSO4, filtered andconcentrated in vacuo to give the crude product which was purified as specified below.

The synthetic route of 4-Bromoisatin has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISIS INNOVATION LIMITED; CHRISTOU, Ivy; CROSS, Rebecca Lillian; GIANELLA-BORRADORI, Matteo; GREAVES, David Robert; RUSSELL, Angela Jane; WYNNE, Graham Michael; WO2013/41859; (2013); A1;,
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Related Products of 400727-63-1, 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. 400727-63-1, name is tert-Butyl 5-nitroisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer was charged with tert-butyl 5-nitroisoindoline-2-carboxylate (650 mg, 2.5 mmol) and C2H5OH (50 mL). This solution was hydrogenated with Pd/C (160mg) at room temperature for 15 h. It was then filtered and the filtrate was concentrated under reduced pressure to afford 231c as a yellow oil (585 mg, 99%), which was used in the next step without further purification. MS: [M+H]+ 179.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 5-nitroisoindoline-2-carboxylate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
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5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-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 2-(Bromomethyl)isoindoline-1,3-dione

Dimethyl (phthalimidomethyl)phosphonate (ii). A mixture of N-(bromomethyl) phthalimide (i) (10.43 g, 43.46 mmol) and trimethyl phosphite (5.93 g, 47.80 mmol) was heated at reflux in xylene (20 mL) for 6 h. The reaction mixture was then cooled to room temperature and concentrated. Crystallization from CHCl3-hexane gave (ii) (7.60 g, 65%) as a white solid: 1H NMR (300 MHz, CDCl3) deltaH 3.84 (d, JH,P=10.8 Hz, 6 H), 4.12 (d, J=11.4 Hz, 2 H), 7.76 (m, 2 H), 7.87 (m, 2 H).

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

Reference:
Patent; MethylGene, Inc.; US6884791; (2005); B2;,
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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. 4702-13-0, name is N-Phthaloylglycine, A new synthetic method of this compound is introduced below., COA of Formula: C10H7NO4

(a) Preparation of 1,3-dihydro-1,3-dioxo-2H-isoindole-2-acetyl chloride STR10 A solution of 1,3-dihydro-1,3-dioxo-2H-isoindole-2-acetic acid (7.00 g) and thionyl chloride (12 mL) was stirred at reflux under nitrogen for one hour. The thionyl chloride was distilled from the reaction, and the resulting crude product was further purified by distillation via a kugelrohr apparatus (BUCHI, Flawil, Switzerland). [Bp: 160-180 C. (oven temperature) at 10 mm Hg.]The yield of the title compound was 6.88 grams (90.2%). The structure of the title compound, and of all of the compounds synthesised in each of the subsequent examples, was confirmed by 1 H NMR.

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; G. D. Searle & Co.; US5212169; (1993); A;,
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954-81-4, name is N-(5-Bromopentyl)phthalimide, 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. category: indolines-derivatives

To a stirred solution of compound 14-k (80 g, 0.27 mol) in DMF (745 mL) was added potassium thioacetate (34 g, 0.29 mol) portion wise over 20 min at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 min. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (1 L) and stirred for 1 h. The resultant precipitate was filtered, washed with water (500 mL) and dried in vacuo to afford 15-k as an off-white solid (75 g, 95%).1H NMR (400 MHz, CDC13): delta 7.84 (dd, J= 5.5 Hz, 3.0 Hz, 2H), 7.71 (dd, J= 5.5 Hz, 3.1 Hz, 2H), 3.67 (t, J= 7.3 Hz, 2H), 2.85 (t, J= 7.3 Hz, 2H), 2.30 (s, 3H), 1.73-1.65 (m, 3H), 1.64-1.57 (m, 1H), 1.46-1.37 (m, 2H);LC-MS: 292.2 (M++l).

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; LADNER, Robert, D.; (244 pag.)WO2018/98208; (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. 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Product Details of 5394-18-3

Preparation of l-Cyclohexyl-N-(4-(4-(6-nitropyridin-2-yl)piperazin-l- yl)butyl)methane-sulfonamide (Method A)N-(2-Bromobutyll)-phthalimide (2.82 g, 10 mmol) was dissolved in acetonitrile (6 mL) and 1-Boc-piperazine (1.82 g, 10 mmol) then diisopropylethylamine (1.87 mL, 10.74 mmol) were added at ambient temperature. The reaction mixture was split into two 10 mL microwave glass tubes then heated at 130 C for 15 min in the microwave oven.TLC (ethyl acetate/petrol 1: 1) showed a small amount of starting materials still present and a major product. The reaction mixture was evaporated to dryness and the yellow residue was dissolved in dichloromethane (20 mL) and washed with 10% aqueous potassium carbonate (30 mL), then the aqueous layer was washed twice with dichloromethane (10 mL). The organic layers were combined then evaporated to dryness to give a yellow oil which was purified by chromatography on silica gel (50 g) using 5-100% ethyl acetate in petrol gradient to at a flow of 40 mL/min to give the product as a white solid 3.1 g (80%).LCMS: calcd for C21H29N3O4 387.2; found 388.2 [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; GE HEALTHCARE LIMITED; MEDI-PHYSICS, INC.; NEWINGTON, Ian, Martin; WYNN, Duncan George; NAIRNE, Robert James Domett; GUILBERT, Benedicte; MANDAL, Subrata; JINTO, Jose; VARADARAJAN, Sunderaraman; RANGASWAMY, Chitralekha; BETTS, Helen; DAVIS, Rebecca; WO2011/150183; (2011); 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 3335-98-6 as follows. Safety of 1-Phenyloxindole

A typical procedure: Tf2O (203 mg, 0.72 mmol) in CH2Cl2 (5 mL) were added at room temperature to a solution of azulene (1) (67 mg, 0.52 mmol) and 2-indolinone (101 mg, 0.76 mmol) in CH2Cl2 (15 mL). The resulting solution was stirred at the same temperature for 2.5 hours. The reaction mixture was poured into a 2 M K2CO3 solution, extracted with AcOEt, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel with hexane/AcOEt (10:1) as an eluent to give 1-(indol-2-yl)azulene (2) (113 mg, 89%) as green crystals.

According to the analysis of related databases, 3335-98-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shoji, Taku; Inoue, Yuta; Ito, Shunji; Tetrahedron Letters; vol. 53; 12; (2012); p. 1493 – 1496;,
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Adding a certain compound to certain chemical reactions, such as: 675109-26-9, name is 6-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 675109-26-9, SDS of cas: 675109-26-9

Preparation 48: 6-bromo-2-[2-(morpholin-4-yl)ethyl]-2,3-dihydro-1 H-isoindol-1 -one (1544) (1545) Sodium hydride (60% dispersion in mineral oil, 34 mg, 1.40 mmol) was added to a suspension of 6-bromo-2,3-dihydro-1 H-isoindol-1 -one (250 mg, 1.18 mmol) in DMF (5 mL) and the mixture was stirred for 5 min after hydrogen gas evolution ceased. 4-(2-bromoethyl)morpholine (0.18 mL, 1.3 mmol) was added to the resulting brown solution and the mixture was stirred at RT for 18 h. The mixture was diluted with ethyl acetate and transferred into a separating funnel. Water was added and the crude product was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgS04) and concentrated under vacuum. The residue was triturated with a mixture of diethyl ether and iso-hexane and the resulting precipitate was filtered, washed with iso-hexane and dried under suction to afford the title compond (196 mg, 50%) as a pale yellow solid. LC-MS: [M+H]+ = 325/327.

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, 6-Bromoisoindolin-1-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OTSUKA PHARMACEUTICAL CO., LTD.; BERDINI, Valerio; BUCK, Ildiko Maria; DAY, James Edward Harvey; GRIFFITHS-JONES, Charlotte Mary; HEIGHTMAN, Thomas Daniel; HOWARD, Steven; MURRAY, Christopher William; NORTON, David; O’REILLY, Marc; WOOLFORD, Alison Jo-Anne; COOKE, Michael Liam; COUSIN, David; ONIONS, Stuart Thomas; SHANNON, Jonathan Martin; WATTS, John Paul; (867 pag.)WO2017/68412; (2017); A1;,
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Electric Literature of 132898-96-5,Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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: To a stirred solution of the N-Boc-protected pyrrolidine (1.0 mmol) in dry DCM (3 mL) at 0 C under argon atmosphere, TFA (1.14 g, 10.0 mmol) was added dropwise. The obtained solution was stirred at 0 C for 30 min followed by stirring at r.t. for 2 h. Subsequently, the solution was poured to cold 10% aq. NaOH (15 mL) and extracted with DCM (3 ¡Á 15 mL). The combined organic phases were dried over MgSO4 and concentrated under reduced pressure resulting in the corresponding unprotected pyrrolidine, which was used in the next step without further purification. The free pyrrolidine (ca. 1 mmol) from the previous step was then taken up in CHCl3 (2.2 mL) and DIPEA (2.0 mmol) was added. The solution was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.5 mmol) in CHCl3/THF (1:1, 15 mL) at room temperature. The resulting mixture was stirred further for 1 h and the solvent was removed under reduced pressure. After purification by flash column chromatography the target isatin sulfonamide was obtained.

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

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
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