Tag: M.W=200-300

Reference of 20870-78-4, 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. 20870-78-4, name is 5-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-bromoindolin-2-one (1.50 g; 6.93 mmol; 1.00 eq) was dissolved in THF (45.00 ml) then di-ferf-butyl dicarbonate (2.29 g; 10.40 mmol; 1.50 eq) and NaHC03 (5.24 g; 62.41 mmol; 9.00 eq) were added. The mixture was stirred 3h under reflux. Solids were filtered and the filtrate was concentrated. The residue was purified by chromatography (gradient from 100% n-heptane to 80/20 n-heptane / EtOAc) to give tert-butyl 5-bromo-2-oxo-indoline-1-carboxylate (1.52 g; 71 %) 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, 5-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eng Bang Tiba; Ba Seu-ma-tin; Kon Tal-sil-bi-e; Ju Ni-en-jang—ru-i-seu; Ma Sa-reu-di-e-reu-keu-ri-seu-tin; Mon Tal-be-ti-keu-ri-seu-chan; Su Deu-an-ne; (111 pag.)KR2019/137803; (2019); A;,
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Related Products of 4403-36-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 4403-36-5 name is 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Triethylamine (50 muL), DMAP (catalytic amount) and 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl) -ethanesulfonyl chloride (27.4 mg, 0.10 mmol) were added to 0.034 mmol 45. The reaction mixture was stirred at room temperature for 18 hours under an inert atmosphere. The reaction was monitored by TLC (EtOAc/hexane 3/7) (Rf 44 = 0.5, Rf45 = 0, Rf 268 = 0.4) and LC/MS. After completion of the reaction, the mixture was diluted with EtOAc (20mL) and washed with 1N HCl, saturated NaHCO3 and brine. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethylacetate/hexane-3/7) to afford 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethanesulfonic acid 9-benzhydryloxy-7-(4-fluoro-benzyl)-8-oxo-7,8-dihydro-6H-pyrrolo[3,4-g]quinolin-5-yl ester 268 (12.2 mg, 50%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(1,3-Dioxoisoindolin-2-yl)ethanesulfonylchloride, and friends who are interested can also refer to it.

Reference:
Patent; Gilead Sciences, Inc.; WO2004/35576; (2004); A2;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1254319-51-1, name is 6-Bromo-2-methylisoindolin-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 1254319-51-1, Recommanded Product: 6-Bromo-2-methylisoindolin-1-one

General procedure: 5-Bromo-2-methylisoindolin-1-one (520 mg, 2.30 mmol) and thiophene-2-boronic acid (442mg, 3.45 mmol) were dissolved in a mixure of toluene (12 mL) and EtOH (6 mL). A solutionof 2 M Na2CO3 (3 mL) and Pd(dppf)Cl2 (94 mg, 0.12 mmol) were added and the entiremixture heated at reflux under N2 for 2 h. Additional thiophene-2-boronic acid (294 mg, 2.30mmol) was added and reflux continued under N2 overnight. Upon cooling, the mixture wasdiluted with water (100 mL) and extracted with CH2Cl2 (6×50 mL). The combined organicfractions were dried (Na2SO4), filtered, and the solvent removed under reduced pressure togive a crude solid which was purified by flash column chromatography on silica gel (EtOAcas eluant). The title compound was isolated as a light-brown solid (510 mg, 97%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromo-2-methylisoindolin-1-one, and friends who are interested can also refer to it.

Reference:
Article; Spicer, Julie A.; Miller, Christian K.; O’Connor, Patrick D.; Jose, Jiney; Huttunen, Kristiina M.; Jaiswal, Jagdish K.; Denny, William A.; Akhlaghi, Hedieh; Browne, Kylie A.; Trapani, Joseph A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 4; (2017); p. 1050 – 1054;,
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Indoline | C8H9N – PubChem

Reference of 169037-23-4, These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, 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: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-(o-methoxyphenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(o-methoxyphenyl)-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5j): Melting point 295-297 C; White solid, 92%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 5.00 (d, J = 14.64 Hz, 1H), 4.69-4.72 (m, 1H), 4.41 (d, J = 10.24 Hz, 1H), 3.87 (d, J = 13.92 Hz, 1H), 3.83 (s, 3H), 3.81 (s, 3H), 3.72 (d, J = 16.92 Hz, 1H), 3.55 (d, J = 15.4 Hz, 1H), 3.05 (d, J = 11.72 Hz, 1H), 2.84-2.90 (dd, J = 13.96, 8.08 Hz, 1H), 2.75 (d, J = 13.92 Hz, 1H), 6.62-6.68(m, 2H), 6.99-7.58 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 39.7, 47.4, 52.7, 53.3, 55.4, 55.5, 61.2, 67.4, 70.9, 100.9, 109.8, 114.1, 114.3, 121.3, 122.4, 124.6, 124.9, 126.5, 127.4, 128.6, 128.7, 128.6, 128.7, 129.4, 129.8, 130.2, 130.5, 131.7, 134.5, 136.8, 138.4, 138.5, 138.7, 139.8, 139.9, 140.2, 144.4, 179.3, 197.5. EI-MS: m/z 771 (M+). Anal. Calcd for C46H40F3N3O5: C, 71.58; H, 5.22; N, 5.44. Found: C, 71.69; H,5.36; N, 5.58.

Statistics shows that 5-(Trifluoromethoxy)indoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 169037-23-4.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
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These common heterocyclic compound, 18711-15-4, name is 4,6-Dichloroisatin, 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: 18711-15-4

3) Intermediate I-3; 2-amino-4,6-dichloro benzoic acid; At room temperature, to a solution of the intermediate I-2 (5.0 g, 23.1 mmol) prepared by the above peparation example I(2) in 75 mL 1N NaOH (aq) was added portionwise hydrogen peroxide (28 % v/v, 10 mL). The reaction mixture was filtered after stirring for 2 hours to remove insoluble dark brown solid. The filterate was then carefully acidified to pH 2 by conc. hydrochloric acid. The formed yellow precipitates were collected, washed with water, and dried in vacuo. The objective compound (3.90 g, 82 %) was obtained as ivory-colored solid by recrystalization from benzene: TLC Rf = 0.1 (EtOAc:n-hexane = 1:1); m.p. 188 – 189 C; 1H NMR (DMSO-d6) delta 6.76 (d, J = 1. 9 Hz, 1H, ArH), 6.85 (d, J = 1. 9 Hz, 1H, ArH); MS(EI) m/e 206[M+], 162[M+-CO2].

The synthetic route of 4,6-Dichloroisatin has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; EP1650190; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 147149-84-6,Some common heterocyclic compound, 147149-84-6, name is 4-Bromo-5-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: To a microwave reaction tube were added indoles (2 mmol), isatins (1 mmol) and HFIP (2 mL). After sealing the tube, the mixture was heated to 75C in an oil bath and stirred for 1 h. After completion of the reaction (monitored by TLC), the reaction mixture was cooled to room temperature, and the resulting precipitate was then filtered, washed with ether, and dried to give compound 3a-3q and 4a-4j.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-5-methylindoline-2,3-dione, its application will become more common.

Reference:
Article; Cheng, Jialing; Liu, Hong-Min; Wang, Shuai; Yu, Bin; Yuan, Xiaohan; Chinese Chemical Letters; (2020);,
Indoline – Wikipedia,
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Application of 193354-13-1, 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. 193354-13-1, name is 5-Iodoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 mL of methanol, 15 mL of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane). The fractions containing product were concentrated and allowed to stand. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

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

Reference:
Patent; Sugen, Inc.; US6486185; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, 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. category: indolines-derivatives

General procedure: The isatin ( 0.01 mol scale) was dissolved in 50 ml of CH3OH in a 150 ml round bottomed flask equipped with a reflux condenser and a stir bar. The mixture was brought to reflux that was followed by gradual addition of KBH4 (0.27 g, 0.005 mol). The reaction mixture continued to stir under reflux for 1 hour. While heating, the stopper of the round bottomed flask was removed 2-3 times and the flask was shaken to saturate the reaction mixture with air. After 1 hour, the solution was cooled to room temperature and the indirubin precipitated out of the solution. The solid was isolated by filtration and was further purified by recrystallization from 95% C2H5OH or by column chromatograph on silica gel. Indirubin and 10 indirubin derivatives in Z form were synthesized by this method. The structures of the indirubins were determined by 1H NMR, 13C NMR, MS, IR, UV and elemental analysis, and the stereochemistry was assigned by comparing the spectra data to published reports or comparing to authentic samples.

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

Reference:
Article; Wang, Cuiling; Yan, Jiaxu; Du, Mo; Burlison, Joseph A.; Li, Chi; Sun, Yanni; Zhao, Danqing; Liu, Jianli; Tetrahedron; vol. 73; 19; (2017); p. 2780 – 2785;,
Indoline – Wikipedia,
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Related Products of 5181-35-1, 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. 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-(2- bromoethoxy)isoindoline- l,3-dione (5 g, 1.85 mmol, product from step 1 of preparation 10) and lH-tetrazole (1.3 g, 1.85 mmol) in dimethylformamide (25 ml) was added cesium carbonate (6.0 g, 1.85 mmol) in a lot wise under stirring at room temperature. The progress of reaction was monitored by performing thin layer chromatography using mixture of acetone and hexane (3.5:6.5) as solvent. After 16 hours the completion of the reaction was confirmed by thin layer chromatography. The reaction mixture was slowly poured into chilled water (200 ml) under stirring. After stirring for 30 minutes, the precipitates formed were filtered and washed with water (50 ml). The solid compound was dried at 40 C for 2 hours under high vacuum to provide 3.2 g of a mixture of 2-[2-(lH-tetrazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)-dione and 2-[2-(2H-tetrazol-2- yl)ethoxy]- lH-isoindole- l,3(2H)-dione in 66% yield.

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-(2-Bromoethoxy)isoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

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;,
Indoline – Wikipedia,
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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., Recommanded Product: 675109-26-9

[1532] to a solution of 6-bromoisoindolin-1-one (0.5 g, 2.36 mmol) in acetone (20 ml) was added bnbr (605 mg, 3.54 mmol, 0.420 ml),Cs2CO3 (1.92 g, 5.90 mmol) and 18- crown-6 (62 mg, 235.80 umol), then the mixture was stirred at 70 C for 16h. The reaction mixture was concentrated to remove solvent, then diluted with water (50 ml) and extracted with ea (40 ml x 2), and the organic layers were dried over Na2SO4, filtered and concentrated to give a residue. The residue was purified by flash silica gel chromatography (isco; 12 g sepaflash silica flash column, eluent of 0-20% ethyl acetate/petroleum ethergradient 30 ml/min). Compound 378a (0.46 g, yield: 59.5%) was obtained as white solid. 1H NMR (400mhz, CDCl3) delta 8.02 (d, j = 1.8 hz, 1h), 7.63 (dd, j = 1.9, 8.0 hz, 1h), 7.39 – 7.16 (m, 6h), 4.79 (s, 2h), 4.21 (s, 2h). MS (ESI) m/z (M+H)+ 302.0.

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; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem