Month: April 2021

Reference of 40314-06-5, These common heterocyclic compound, 40314-06-5, name is 5-Methylisoindoline-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.

Isolation and analytic data for 14, observed in the crossover study, was obtained by independent preparation using the following procedure. Benzoyl chloride (62 muL, 0.54 mmol) was added to a mixture of 4-methylphthalimide (200 mg, 1.2 mmol), isobutyraldehyde (108 muL, 1.19 mmol), NaI (160 mg, 1.1 mmol), 4 A MS (100 mg), triethylamine (150 muL, 1.1 mmol), ethyl acetate (1.1 mL), and acetonitrile (1.1 mL) at room temperature and with stirring. After 24 h, the mixture was diluted in EtOAc and washed with 1 M NaOH (3¡Á) and brine. The organic phase was dried (MgSO4) and concentrated. Purification by flash chromatography (SiO2, hexanes:EtOAc 6:1) gave 14 (145 mg, 0.43 mmol, 80%) as a yellow oil. 1H NMR (300 MHz, CDCl3): delta 8.09 (d, J=7.7Hz, 2H), 7.75 (d, J=7.6Hz, 1H), 7.67 (s, 1H), 7.50-7.60 (m, 2H), 7.43 (dd, J=7.6, 7.8Hz, 2H), 6.46 (d, J=10.4Hz, 1H), 3.09 (nfom, 1H), 2.50 (s, 3H), 1.15 (d, J=6.7Hz, 3H), and 0.96 (d, J=6.8Hz, 3H). 13C NMR (75 MHz, CDCl3): delta 167.1, 167.0, 165.3, 145.8, 135.0, 133.5, 131.9, 130.0, 129.4, 128.9, 128.5, 124.2, 123.7, 79.7, 29.8, 22.1, 19.1, and 18.0. IR (neat): 2965, 2938, 2874, 1780, 1748, 1720, 1469, 1373, 1359, 1223, and 720 cm-1. HRMS (ESI-TOF): Calcd for C20H19NNaO4+ [M+Na+] requires 360.1206; found 360.1223.

The synthetic route of 40314-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Enright, Robert N.; Grinde, Jeffrey L.; Wurtz, Lincoln I.; Paeth, Matthew S.; Wittman, Tekoa R.; Cliff, Emily R.; Sankari, Yessra T.; Henningsen, Lucas T.; Tan, Chuchen; Scanlon, Joseph D.; Willoughby, Patrick H.; Tetrahedron; vol. 72; 41; (2016); p. 6397 – 6408;,
Indoline – Wikipedia,
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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., SDS of cas: 2058-72-2

General procedure: 11H-indeno[1,2-b]quinoxalin-11-one 2a (0.23?g, 1.00?mmol) and TosMIC (0.20?g, 1.10?mmol) was poured into the mixture of ethanol (1.00?mL) and K2CO3 (0.14?g, 1.00?mmol), and stirred for 10?min?at ambient temperature. After that, the reaction mixture was diluted with water (3.00?mL), the resulting precipitate was filtered, and washed with water.

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shaabani, Ahmad; Sepahvand, Heshmatollah; Bazgir, Ayoob; Khavasi, Hamid Reza; Tetrahedron; vol. 74; 49; (2018); p. 7058 – 7067;,
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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 446292-08-6

20 g of 2-({(5S) -2-oxo-3-[4-(3-oxomo holin-4-yl) henyl]-1 ,3-oxazolidin-5-yl}methyl)-1H- isoindole-1,3(2H)-dione was suspended in 450 ml of ethanol, which was followed by addition of 6 ml of hydrazinehydrate in 50 ml of ethanol and the mixture was stirred and refluxed for 3 hours. Then, the suspension was cooled down to 65C and filtered and the cake was washed with 2×50 ml of nearly boiling ethanol. After drying 7.2 g of an off-white powder were obtained, which slowly melted at a temperature over 260C (this fraction contained 99.9% of 2,3-dihydrophtalazine-l,4-dione according to HPLC). After cooling of the hot filtrate another solid fraction separated. After its isolation by filtration and drying, 12.5 g of white lumpy powder with the melt, point of 141-144C was obtained (this fraction contained 86.7% of the desired product, 12.7% of 2,3-dihydrophtalazine-l,4-dione, and the rest to 100 % were other unidentifiable impurities according to HPLC). The yield of the isolated amine calculated to the pure substance was 73%.

According to the analysis of related databases, 446292-08-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ZENTIVA, K.S.; HALAMA Ales; KRULIS Radim; DAMMER, Ondrej; KALASEK, Stanislav; WO2013/120465; (2013); 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. 199328-10-4, name is Methyl Oxindole-5-carboxylate, A new synthetic method of this compound is introduced below., category: indolines-derivatives

Step 2: Synthesis of 5-Carboxy-2-oxindole. 5-Methoxycarbonyl-2-oxindole (1 g) and 1 g of sodium hydroxide in 20 mL of methanol was refluxed for 3 hours. The reaction mixture was cooled and concentrated to dryness. The residue was dissolved in water and extracted twice with ethyl acetate. The aqueous layer was acidified with 6 N hydrochloric acid and the precipitated solid collected, washed with water, and dried to give 0.7 g (78%) of the title compound as an off-white solid.

The synthetic route of 199328-10-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sugen, Inc.; US6147106; (2000); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Formula: C8H8N2O2

A solution of 5-nitroindoline (1.033 g, 6.30 mmol), TEA (0.827g, 8.19 mmol) in DCM (30 mL) at 0C was slowly added methylsufonyl chloride (0.868 g, 7.56 mmol). The mixture was warmed up and stirred at room temperature for 0.5 h. The reaction was quenched with water (30 mL) and extracted with DCM (25 mL x4). The organic layers were combined, dried and concentrated under reduced pressure to afford crude 1 (1.427 g, 5.9 mmol, yield 95%), which was used for next step without further purification.

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; ACEA BIOSCIENCES INC.; XU, Xiao; WANG, Xiaobo; MAO, Long; ZHAO, Li; XI, Biao; WO2015/6754; (2015); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6941-75-9, 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 6941-75-9 as follows.

(B) Synthesis of Compound 31-c 194 ml of fuming nitric acid (fum. HNO3) was added to 0.9 L of concentrated sulfuric acid under stirring and cooling in an ice water bath. The mixture was stirred for 1 hour under cooling in an ice water bath, and then 215 g of Compound 31-a was added slowly to the mixture in portions over 30 minutes, while an inside temperature was maintained at 15 C. or lower. After completion of the addition, the mixture was stirred at room temperature for 8 hours. The reaction liquid was poured into 1 L of ice water, to precipitate crystals. After stirring, the crystals were collected through filtration, and washed with running water. The thus-obtained crude crystals of Compound 31-b were transferred to another flask without purification. 1 L of DMF was added thereto, and the whole was stirred at room temperature. To the resultant suspension, 200 ml of 25% ammonia water was added under stirring, and the mixture was stirred at room temperature for 3 hours. The crystals were collected through filtration, and added to 1.5 L of isopropyl alcohol. The mixture was refluxed under heating for 30 minutes, and then stirred at room temperature for 3 hours. The crystals were collected through filtration, washed with running hexane, and dried, to thereby obtain 131 g (48% yield from Compound 31-a) of Compound 31-c.

According to the analysis of related databases, 6941-75-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUJI PHOTO FILM CO., LTD.; US2006/142553; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., name: 2-(Bromomethyl)isoindoline-1,3-dione

0.021 mol (4.99 g) of 2-(bromomethyl)-1H-isoindole-1,3(2H)-dione ( Sigma-Aldrich) was added to a solution of 4.04 g (0.020 mol) of the compound XA0 obtained in substage 1.1) of Example 1 in 35 ml of acetone (Sigma-Aldrich), in an ice bath (highly exothermic reaction). Once the addition was complete, the reaction medium was stirred at ambient temperature for 3 hours and then filtered. The filtrate was concentrated under vacuum in order to obtain the expected product XA2 in the form of a yellow oil (5.84 g, yield 91%) which will be used in the following stage without purification.

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; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITE TOULOUSE III – Paul Sabatier; COUTELIER, Olivier; DESTARAC, Mathias; LANGLAIS, Marvin; (16 pag.)US2019/359603; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 13861-75-1, A common heterocyclic compound, 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, molecular formula is C10H9NO, 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.

Step 2: Spiro [cycJ.opropane-1, 3 ?-indoline]To mixture of spiro[cyclopropane-l, 3?-indoiine]-2?-one(35.0 g, 219.87 mmol) in THF? (750 mL) was slowly added lithiumaluminium hydride (2M solution in THF) (219.9 mL, 439.7 mrnol) at 0C. The resulting mixture was allowed to be warmed to room temperature and then heated to reflux for 18 hour under argon atmosphere. Upon completion as monitored by TLC, the reactionmixture was cooled to room temperature, quenched with ice, basified with aqueous ammonia, and extracted with ethyl acetate (2 x 750 mL) . The combined organic layers were washed. successively with water (100 rn) and brine (100 mL), dried over sodium sulfate and concentrated under vacuum to obtain acrude oily product (32 g, 100%) . The product was subjected tonext reaction without further purification.MS(ESI)m/z: 146.1[M+1] ; ?HNMR (400 MHz, DMSO-d6) : 5 0.88 (s, 4H)3.43 (S. 21-{), 5.54 (s, 1H), 6.44-6.55 (m, 3H), 6.85 (t, J =7.6 Hz, 1M).

The synthetic route of 13861-75-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; DESHPANDE, Anil M.; BARAWKAR, Dinesh; PATIL, Santosh; BANKAR, Digambar; (178 pag.)WO2016/88903; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1201923-48-9, 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. 1201923-48-9 name is (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate, 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.

To a solution of 1 ,1-dimethylethyl 1 ,1-dimethylethyl {(1 S)-2-(1 ,3-dioxo-1 ,3-dihydro-2/-/-isoindol-2-yl)-1-[(3-fluorophenyl)methyl]ethyl}carbamate (9.0 g, 22.6 mmol) in DCM (200 ml.) at RT was added 4M HCI in dioxane (56 ml_, 226 mmoles). After 12h, the solution was filtered and washed with DCM (50 ml.) affording the title compound (7.8 g,99%) as a white HCI salt: LCMS (ES) m/z 349 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (S)-tert-Butyl (1-(1,3-dioxoisoindolin-2-yl)-3-(3-fluorophenyl)propan-2-yl)carbamate, and friends who are interested can also refer to it.

Reference:
Patent; SMITHKLIKE BEECHAM CORPORATION; WO2009/158371; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 35197-64-9, 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 35197-64-9 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.

According to the analysis of related databases, 35197-64-9, the application of this compound in the production field has become more and more popular.

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);,
Indoline – Wikipedia,
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