Author: Jessica.F

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. Formula: C9H4F3NO3

General procedure: A mixture of indoline-2,3-dione 1 (1mmol), l-tryptophan (2a) or l-histidine 2b (1mmol) and (E)-(2-nitrovinyl)benzene 3 (1.1mmol) was heated while stirred in [bmim]Br as the reaction medium (3mL) for 1hat 100C. After completion of the reaction (TLC), EtOAc (5mL) was added and the reaction mixture was stirred for 10min. This treatment was repeated and the combined ethyl acetate layers were removed in vacuo. The crude product was purified by recrystallization of the residue from EtOH (compounds 4) or by column chromatography (compounds 5). After extraction of the product, the ionic liquid was dried under vacuum at 80C for 2h to eliminate any water and could be reused for subsequent runs of the reaction.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Periasamy, Vaiyapuri Subbarayan; Athinarayanan, Jegan; Alshatwi, Ali A.; Govindasami, Periyasami; Altaf, Mohammad; Menendez, J. Carlos; Tetrahedron; vol. 74; 38; (2018); p. 5358 – 5366;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 496-12-8,Some common heterocyclic compound, 496-12-8, name is Isoindoline, molecular formula is C8H9N, 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: j0444] A flame-dried 50-mE round-bottomed flask, equipped with a Teflon stir bar, was charged with 2-substituted N-aryl pyrrolidine (1 mmol, 1 equiv.), and degassed CH2C12:H20 (1:1, 25-mE). Then, sodium periodate (641.7 mg, 3.0 mmol, 3.0 equiv.) was added to the phenol solutionand the reaction was stirred for 4 h. Then, the reaction mixture was quenched by the addition of NaHSO4 (10 mE, 10% by weight aqueous solution), and the phases were separated, and the aqueous phase was washed with CH2C12 (3×20 mE). The organic fraction was dried over Mg504, filtered and concentrated in vacuo to afford a crude residue, which was purified using flash column chromatography (silica gel with 15% EtOAc in hexanes as eluant) to afford a white powder in 95% isolated yield.

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

Reference:
Patent; THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING/MCGILL UNIVERSITY; LUMB, JEAN-PHILIP; ESGUERRA, KENNETH V.N.; (118 pag.)US2017/66711; (2017); A1;,
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Indoline | C8H9N – PubChem

Electric Literature of 35197-64-9, 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. 35197-64-9, name is 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In this work, previously reported N-benzyl-2-bromo-4-(1,3-dioxoisoindolin-2-yl)butanamide derivatives (25a-e) [44] were obtained by activating the carboxylic acid group of 24 (1 eqv) by using n-propanephosphonic acid anhydride (T3P, 50% in EtOAc, 1 eqv). The reaction was carried out under argon atmosphere for 2hat 0C in dry methylene chloride. Then, distilled triethylamine (1.2 eqv) and the appropriate N-benzylamine (1.1 eqv) were added to the reaction mixture [57]. The reaction was continued at room temperature for 12h. The products were purified by column chromatography over silica gel (DCM/acetone=9:1) to yield 25a-e as a white solid.

The chemical industry reduces the impact on the environment during synthesis 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Article; ?mudzki, Pawe?; Fija?kowski, ?ukasz; Furga?a, Anna; Gryz?o, Beata; Hoefner, Georg C.; Kulig, Katarzyna; Malawska, Barbara; Malawska, Katarzyna; Nowaczyk, Alicja; Podkowa, Adrian; Rapacz, Anna; Sa?at, Kinga; Wanner, Klaus T.; Zar?ba, Paula; European Journal of Medicinal Chemistry; vol. 188; (2020);,
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Electric Literature of 317-20-4, 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. 317-20-4, name is 7-Fluoroisatin, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a 25 mL round bottom flask, isatins 1 (1 mmol), 3-phenylisoxazol-5(4H)-one 2 (1 mmol) or 3-ethylisoxazol-5(4H)-one 7 (1 mmol), pyrazol-5-amine 3 (1 mmol) or 6-aminopyrimidine-2,4-(1H,3H)-dione 5 (1 mmol), and Amberlyst-15 (100 mg) were stirred in CH3OH (5.0 mL) at 80 C. When the reaction was completed (detected by TLC), the spherical catalyst was separated by a sieve at once under hot condition. Then, the reaction mixture was cooled to room temperature, and solid precipitation occurred. After filtration, the crude product was recrystallized from EtOH and DMF to give pure compound.

The chemical industry reduces the impact on the environment during synthesis 7-Fluoroisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Niu, Qingqing; Xi, Junhua; Li, Lei; Li, Li; Pan, Chengli; Lan, Meijun; Rong, Liangce; Tetrahedron Letters; vol. 60; 43; (2019);,
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Related Products of 100510-65-4,Some common heterocyclic compound, 100510-65-4, name is 6-Amino-3,3-dimethylindolin-2-one, molecular formula is C10H12N2O, 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.

Step B: 6-(4-(2,2-Difluoroethylamino)furo[3,2-i/|pyrimidin-2-ylamino)-3,3-dimethylindolin- -oneTo a vial was added Pd2dba3 (0.235 g, 0.257 mmol), Cs2C03 (2.37 g, 7.28 mmol) and Ru-Phos (0.240 g, 0.514 mmol) in i-AmOH (8.00 mL). The mixture was evacuated and purged with N2. The mixture was stirred at about 65 C for about 20 min. 2-Chloro-A^-(2,2-difluoroethyl)furo[3,2- i/]pyrimidin-4-amine (1.00 g, 4.28 mmol) and 6-amino-3,3-dimethylindolin-2-one (0.754 g, 4.28 mmol, Astatech) were added in one portion. Additional i-AmOH (12.00 mL) was added. The mixture was evacauted and purged with N2. The mixture was stirred at about 70 C for about 5 h, stirred at about 60 C for about 15 h and then stirred at about 75 C for about 2 h. The mixture was cooled to rt and filtered. The precipitate was washed with DCM (20 mL) and MeOH (20 mL). The combined filtrate was concentrated and purified by column chromatography eluting with 25-65% EtOAc/heptane (40 g silica gel) to give a crude material. The material was suspended in Et20 (about 15 mL) and sonicated. The suspension was filtered and washed with Et20 (50 mL), then with DCM (about 30 mL). The precipitate was dissolved in DCM (50 mL), combined with filtrate, concentrated under reduced pressure, dissolved in MeOH (40 mL), and adsorbed onto silica gel (MeshNo. 200-400, 60A; 3 g). The material was purified by column chromatography eluting with 0 to 28% of 10% MeOH/DCM and DCM (40 g silica gel) to give a solid. The solid was purified by mass-triggered HPLC (Table 2, Method x) purification to give 6- (4-(2,2-difluoroethylamino)furo[3,2-i/]pyrimidin-2-ylamino)-3,3-dimethylindolin-2-one(0.397 g, 25%): LC/MS (Table 2, Method c) R, = 1.75 min.; MS m/z: 374 (M+H)+. Syk IC

The synthetic route of 100510-65-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; CALDERWOOD, David, J.; WILSON, Noel, S.; COX, Philip; HOEMANN, Michael, Z.; CLAPHAM, Bruce; MULLEN, Kelly, D.; VASUDEVAN, Anil; VILLAMIL, Clara I; LI, Bin; SOMAL, Gagandeep; WO2012/48222; (2012); A1;,
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Indoline | C8H9N – PubChem

Electric Literature of 15861-23-1, 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 15861-23-1 as follows.

Intermediate 10tert-butyl 3-(5-cyanoindolin-l-yl)pyrrolidine-l-carboxylate[0109] To a solution of indoline-5-carbonitrile (110 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-l-carboxylate (166 mg, 0.90 mmol) and HO Ac (0.11 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaC BH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2S04, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.

According to the analysis of related databases, 15861-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HUTCHISON MEDIPHARMA LIMITED; SU, Wei-Guo; DENG, Wei; LI, Jinshui; JI, Jianguo; WO2012/22045; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3416-57-7, These common heterocyclic compound, 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-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.

5.5. Examples 5-13; Similar to Examples 3 and 4,5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol was prepared using the following solvent/base combinations for the preparation of the 2-amino-4-methyl-1H-pyrrole-3-carboxamide intermediate:

The synthetic route of 3416-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bednarz, Mark S.; Kanamarlapudi, Ramanaiah C.; Wu, Wenxue; US2008/97098; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 59-48-3, name is Indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 59-48-3

To the solution of 28a (500mg, 3.76mmol) in acetonitrile (8mL) cooled to – 100C, was slowly added N-bromosuccinimide (770mg, 4.33mmol) with stirring. After the addition was complete, the mixture was stirred for Ih at -1O0C, then warmed to O0C for 2h. The resulting precipitate was collected by filtration, washed with water and dried under vacuo to give 28b (513mg, 64.4%).

According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; XCOVERY, INC.; WO2008/88881; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6941-75-9, 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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of LIALH4 (8.8 mL of 1 M solution in Et20, 8.8 mmol) in dry THF (13 mL) was cooled to 0 C. Concentrated H2S04 (0.42 g, 4.3 mmol) was added dropwise, and the resulting mixture was stirred at 0 C for 30 min. 5-Bromo-lH-isoindole-1, 3 (2H)- dione (0.409 g, 1. 81 mmol) was added in portions over 15 minutes, and the reaction was allowed to warm to room temperature when the addition was complete. The reaction was stirred at room temperature for 2. 5H, and then cooled back to 0 C and quenched by the addition OF MEOH (2 mL). Et2O was added (50 mL), followed by NA2S04-10H20. The mixture was stirred vigorously until the organic layer was clear. The mixture was then filtered and concentrated in VACUO. Purification by column chromatography (4: 1 CH2CL2; MeOH + 0. 1% conc. NH3) provided the title compound (0.128 g, 36%). 1H-NMR (CDCl3): No. 7.38 (s 1H), 7.33 (D,@ J=7. 6 Hz, 1H), 7.12 (d, J=8. 0 Hz, 1H), 4.21 (s, 2H), 4.17 (s, 2H), 2.09 (s, 1H). MS (ESI) (M+H) +=198/200.

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-Bromoisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; WO2004/60882; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 17564-64-6, 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. 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: The initial carbonyl compound (50 mmol) was dissolved/suspended in ethanol (50 mL) and magnetically stirred with thiosemicarbazide (50 mmol) and catalytic amounts of acetic acid for 8-24 h at room temperature. The obtained thiosemicarbazone was filtered, washed with appropriate solvent (n-hexane, petroleumether or diethyl ether) and dried under vacuum. The intermediate thiosemicarbazone (50 mmol) reacted with ethyl bromoacetate (50 mmol), in methanol (50 mL) and sodium acetate (50 mmol) at room temperature under magnetic stirring for 24 h. The resulting 4-thiazolidinone was poured on ice, filtered or extracted with chloroform (3 x 100 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane). Then, the obtained thiazolidinone (50 mmol) was dissolved/suspended in 50 mL of anhydrous acetone in the presence of anhydrous potassium carbonate (50 mmol), and reacted with equimolar amounts of 4-nitrobenzyl bromide, 1-(chloromethyl)naphthalene and N-(chloromethyl)phthalimide for 24-48 h. The product was poured on ice, filtered or extracted with chloroform (3 x 50 mL) and purified by column chromatography (SiO2, ethyl acetate/n-hexane) in order to obtain the title compoundsin high yields. 7.1.57 2-((2-(2-(Hex-5-en-2-ylidene)hydrazono)-4-oxothiazolidin-3-yl)methyl)isoindoline-1,3-dione (5C) White powder, mp 133-135 C, 80% yield; 1H NMR (400 MHz, CDCl3): delta 1.94 (s, 3H, CH3), 2.33-2.39 (m, 4H, 2 * CH2), 3.83 (s, 2H, CH2, thiazolidinone), 4.96-4.98 (m, 1H, =CH2), 5.02-5.07 (m, 1H, =CH2), 5.73 (s, 2H, ArCH2), 5.81-5.87 (m, 1H, CH=), 7.74-7.76 (m, 2H, Ar), 7.86-7.88 (m, 2H, Ar).

The synthetic route of 2-(Chloromethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; De Monte, Celeste; Carradori, Simone; Bizzarri, Bruna; Bolasco, Adriana; Caprara, Federica; Mollica, Adriano; Rivanera, Daniela; Mari, Emanuela; Zicari, Alessandra; Akdemir, Atilla; Secci, Daniela; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 82 – 96;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem