Tag: M.W=200-300

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. 337536-15-9, name is 4-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-Bromoisoindolin-1-one

EXAMPLE 1D 4-(4-aminophenyl)-1-isoindolinone A suspension of Example 1C (2 g, 9.43 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxa-borolan-2-yl)aniline (2.5 g, 11.3 mmol), and Na2CO3 (2.2 g, 20.8 mmol) in DME (68 mL) and water (17 mL) was purged with nitrogen, treated with Pd(PPh3)4 (1 g, 0.9 mmol), and stirred at 90 C. for 19 hours. The reaction mixture was cooled to room temperature, concentrated to one-third its original volume, diluted with ethyl acetate (30 mL) and water (20 mL), and filtered. The filter cake was washed with water and ethyl acetate and dried to give 1.25 g of the desired product. MS (ESI(+)) m/e 225 (M+H)+.

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Curtin, Michael L.; Davidsen, Steven K.; Frey, Robin R.; Heyman, Howard R.; Holms, James H.; Michaelides, Michael; Steinman, Douglas H.; US2005/26976; (2005); A1;,
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Reference of 169037-23-4, 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 162 STR184 Step 1. Preparation of 2-amino-5-(trifluoromethoxy)benzoic acid. 5-(Trifluoromethoxy)isatin (15.0 g, 65 mmol) and potassium hydroxide pellets (4 g) were mixed in water (35 mL) and cooled to 0 C. With vigorous stirring, a solution of 30% aqueous hydrogen peroxide (11.7 g), potassium hydroxide pellets (5.8 g), and water (80 mL) was added drop-wise keeping the temperature below 10 C. After stirring 1 hour at 0 C., glacial acetic acid (22 mL) was added drop-wise, causing foaming and formation of a precipitate. The contents were stirred overnight and filtered to afford the 2-amino-5-trifluoromethoxybenzoic acid as an amber solid (12.5 g, 87%). A small amount was recrystallized from ethyl acetate-hexanes to afford amber needles for an analytical sample and the remaining compound was used without further purification: mp 142.5-144.2 C. 1 H NMR (CDCl3, 300 MHz) 7.98 (s, 1H), 7.18 (d, 1H, J=8.0 Hz) 6.62 (d, 1H, J=8.0 Hz), 6.40 (brs, 2H). Anal. Calc’d for C8 H6 NO3 F3: C, 43.45; H, 2.73; N, 6.33. Found: C, 43.40; H, 2.65; N, 6.35.

The synthetic route of 5-(Trifluoromethoxy)indoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; G.D. Searle & Co.; US6034256; (2000); 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. 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H6BrNO2

General procedure: To a flame-dried screw-capped test tube equipped with a magnetic stir bar was added I, 4,7,10,13, 16-hexaoxacyclooctadecane (0.396 g, 1.5 mmol), KF (0.087 g, 1.5 mmol) and 1- methylindoline-2,3-dione 3 (0.50 mmol). Then the screw-capped tube was evacuated and backfilled with argon. The mixture was dissolved in THF (2.0 mL) under argon atmosphere. The resultant reaction mixture was kept stirring at 30 C for 5 min. To the stirring solution was added pyridine 7 (0.75 mmol) and the aryne precursor 2 (0.75 mmol). When TLC control showed the completion of the reaction (typically after 12 h), the reaction stopped and the crude reaction mixture was purified by column chromatography on silica gel to afford the corresponding indolin 2-one derivatives 8 in good yields.

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 2058-72-2.

Reference:
Patent; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; THANKAPPAN, Biju Akkattu; BHUNIA, Anup; ROY, Tony; WO2014/184808; (2014); A1;,
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Synthetic Route of 959235-95-1,Some common heterocyclic compound, 959235-95-1, name is 6-(Trifluoromethoxy)indoline, molecular formula is C9H8F3NO, 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 mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (590 mg, 2.9 mmol), 2-(2-(4-(fe/t-butoxy)-4-oxobutoxy)-4-chlorophenyl)-2-((3-methoxy-5-(1 /-/-1 ,2,4- triazol-1 -yl)phenyl)amino)acetic acid 11d (1 .5 g, 2.9 mmol), HATU (1 .65 g, 4.35 mmol) and diisopropylethylannine (1 .45 mL, 8.7 mmol) in DMF (60 mL) was stirred at room temperature for 12 h. The mixture was diluted with water. The precipitate was filtered off, washed with water and taken up with EtOAc. The organic layer was washed with water, dried over MgSO4, filtered and the solvent wasconcentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (15-40 muiotatauiota, 120 g, heptane/EtOAc 60/40). The pure fractions were combined and concentrated to dryness to give, after crystallization from ether/diisopropyl ether, terf-butyl 4-(5-chloro-2-(1 -((3-methoxy-5-(1 H-1 ,2,4- triazol-1 -yl)phenyl)amino)-2-oxo-2-(6-(trifluoromethoxy)indolin-1 -yl)ethyl)phenoxy)- butanoate 13a (1 .05 g).

The synthetic route of 959235-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; KATHOLIEKE UNIVERSITEIT LEUVEN; KESTELEYN, Bart Rudolf Romanie; BONFANTI, Jean-Francois; COESEMANS, Erwin; RABOISSON, Pierre Jean-Marie Bernard; MARCHAND, Arnaud Didier M; BARDIOT, Dorothee Alice Marie-Eve; (92 pag.)WO2018/178240; (2018); A1;,
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Application of 201940-08-1, The chemical industry reduces the impact on the environment during synthesis 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, I believe this compound will play a more active role in future production and life.

Reference Example 17 tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate (0344) tert-butyl 5-bromoisoindoline-2-carboxylate (i.e., Matric Scientific, catalog 74109) (20 g, 0.0671 mol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (17 g, 0.0671 mol), KAc (8.5 g, 0.087 mol) and PdCl2dppf (1.8 g, 0.00221 mol) in 200 mL 1,4-dioxane was heated to 80 C. overnight. The mixture was cooled, water was added, the mixture was extracted with EA, dried and concentrated. The residue was purified by chromatography on silica gel to afford the title compound. 1HNMR (300 MHz, DMSO) delta: 1.2-1.3 (s, 12H), 1.4-1.5 (s, 9H), 4.5-4.6 (s, 4H), 7.2-7.3 (m, 1H), 7.5-7.6 (M, 2H); LC-MS: m/z=246 (M+1-100)+.

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, tert-Butyl 5-bromoisoindoline-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Sharp & Dohme Corp.; Mandal, Mihir; Tang, Haifeng; Xiao, Li; Su, Jing; Li, Guoqing; Yang, Shu-Wei; Pan, Weidong; Tang, Haiqun; DeJesus, Reynalda; Hicks, Jacqueline; Lombardo, Matthew; Chu, Hong; Hagmann, William; Pasternak, Alex; Gu, Xin; Jiang, Jinlong; Dong, Shuzhi; Ding, Fa-Xiang; London, Clare; Biswas, Dipshikha; Young, Katherine; Hunter, David N.; Zhao, Zhiqiang; Yang, Dexi; (405 pag.)US2016/333021; (2016); A1;,
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These common heterocyclic compound, 3335-98-6, name is 1-Phenyloxindole, 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. name: 1-Phenyloxindole

General procedure: General Procedure: Under nitrogen atmosphere, to a stirred solution of N-substituted-2-oxindole (10 mmol) in dry Et2O (40 mL) was added LiHMDS (1.0 M in THF solution, 12 mmol, 12 mL) dropwise at 0 C. The solution was allowed to warm to ambient temperature and stirred for 1 h. Then the solution was cooled to 0 C and TMSCl (13 mmol, 1.6 mL) was added dropwise. The solution was allowed to warm to ambient temperature and stirred for another 3 h. The solvent was removed under reduced pressure, and dry MeCN (40 mL) was charged to the flask. The solution was cooled to 0 C again and Selectfluor (12 mmol, 4.3 g) was added to the solution in small portions. The resulting suspension was allowed to warm to ambient temperature and stirred overnight. The reaction was quenched by the addition of water (20 mL) and EtOAc (20 mL). The reaction mixture was extracted with EtOAc (20 mL × 2). The combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure Purification of the crude product was performed by flash column chromatography (Hexane/EtOAc) to afford 3-fluorooxindole.

The synthetic route of 1-Phenyloxindole has been constantly updated, and we look forward to future research findings.

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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Related Products of 2058-72-2,Some common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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: A mixture of isatin derivatives 3 (1 mmol), proline 4 (1 mmol, 0.115 g) and chiral cinamoyl oxazolidinone 1 (1 mmol, 0.293 g) was dissolved in EtOH (80%) (5 mL) and stirred at room temperature for about 5 h. After completion of the reaction (TLC), the solvent was evaporated under reduced pressure, the products (5a-i) were obtained in quantitative yields; and for future purification they were washed with cold EtOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Taghizadeh, Mohammad Javad; Arvinnezhad, Hamid; Samadi, Saadi; Jadidi, Khosrow; Javidan, Abdollah; Notash, Behrouz; Tetrahedron Letters; vol. 53; 38; (2012); p. 5148 – 5150;,
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Application of 20780-77-2, 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. 20780-77-2, name is 6-Iodoindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

c. 7-Iodo-2H-3,1-benzoxazine-2,4(1H)-dione To a stirred warm (80 C.) solution of 6-iodo-1H-indole-2,3dione (3.0 g, 11 mM) in acetic acid (10 mL) and acetic anhydride (10 mL) was added in small portions chromium trioxide (1.83 g, 18.3 mM) while maintaining the temperature of the reaction mixture at 80-90 C. The reaction mixture was then heated at 80 C. for 10 min, cooled and poured into water. The resulting mixture was filtered and the collected solids dried to provide the title compound as a yellow solid (2.6 g, 81.8%); MS(CI): 290 (M+H).

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-Iodoindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Imperial Chemical Industries, PLC; US5599814; (1997); A;,
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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. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Safety of 6-Bromoisoindolin-1-one

6-(5-Hydroxy-pent-1 -ynyl)-2,3-dihydro-isoindolin-1 -oneTo a mixture of 6-Bromo-2, 3-dihydro-isoindolin-1-one (40 g, 0.18 mol), bis(triphenylphosphine) palladium dichloride (6.6 g, 0.009 mol), CuI (3.57 g, 0.01 mol) and Et3N 5 (930 mL) in dry DMF (930 mL) was slowly added 4-pentyn-1-ol (33.2 mL, 0.37 mol). The reaction mixture was bubbled with argon for 20 min and heated at 100 “C for 24 h. The solvent in the reaction mixture was evaporated and the crude residue was washed with DCM(100 mL), filtered and dried to give e-^-Hydroxy-pent-i-ynyl^.S-dihydro-isoindolin-i-one as a black solid (25 g, 61%). 1H-NMR (DMSO-d6, 300 MHz): delta 8.6 (1H, s), 7.5-7.6 (2H, d), 7.5 0 (1H, S), 4.5 (1H, t), 4.3 (2H, s), 3.5 (2H, s), 2.4-2.5 (2H, s), 1.6 (2H, q); MS: AP: M+1: 216(215).

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; PFIZER PRODUCTS INC.; WO2008/20306; (2008); 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. 552330-86-6, name is 5-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 5-Bromoisoindolin-1-one

Step 1: 5-(Ethylthio)isoindolin-1-one (0428) (0429) 5-Bromoisoindolin-1-one (10 g, 47.16 mmol) and sodium ethanethiolate (9.92 g, 117.90 mmol) were mixed together in DMF (100 mL) and the reaction heated to 100 C. for 20 min. The reaction was cooled to room temperature, poured into water (100 mL) and the product extracted with EtOAc (3×200 mL). The combined organic extracts were washed with brine (4×50 mL). LCMS indicated product in the aqueous washings consequently they were combined and extracted with EtOAc (4×50 mL). The organic extracts were combined, dried using a phase separator cartridge and concentrated in vacuo. The solid obtained was dried under high vacuum overnight. 5-(Ethylthio)isoindolin-1-one (8.68 g, 95%) was obtained as a yellow solid. The material was used in the next step without further purification. (0430) LC/MS: m/z=194 [M+H]+. 1H NMR (500 MHz, DMSO-d6) delta 1.27 (t, 3H), 3.06 (q, 2H), 4.33 (s, 2H), 7.36 (dd, 1H), 7.47-7.48 (m, 1H), 7.57 (d, 1H), 8.45 (s, 1H).

The synthetic route of 552330-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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