Category: indolines-derivatives

Application of 99365-40-9,Some common heterocyclic compound, 99365-40-9, name is 6-Bromoindolin-2-one, molecular formula is C8H6BrNO, 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.

2.4 g of 6-bromo-2-indolinone are placed in 60 ml of dimethoxyethane, 1.9 g of phenylboric acid in 8 ml of ethanol and 0.3 g of tetrakistriphenylphosphine palladium are added and to this mixture 12 ml of 2N sodium carbonate solution are added dropwise at ambient temperature.. The mixture is stirred for 6 hours at 85 C. After cooling the catalyst is filtered off, the solvent is eliminated and the residue is washed with 100 ml of water and 20 ml of 1N sodium hydroxide solution.. The residue is purified through a silica gel column with petroleum ether/ethyl acetate (8:2) as eluant. Yield: 1.5 g (65% of theory), Rf value: 0.45 (silica gel, petroleum ether/ethyl acetate=1:1) Melting point: 167-170 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromoindolin-2-one, its application will become more common.

Reference:
Patent; Boehringer Ingelheim Pharma GmbH & Co. KG; US6794395; (2004); B1;,
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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. 16800-68-3, name is 1-Acetylindolin-3-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: A 10 mL glass tube equipped with a stirring bar was charged with the isatin-derived N-Boc ketimine 1 (0.44 mmol, 1.2 equiv), the N-acetylindolin-3-one 2 (0.4 mmol, 1.0 equiv), catalyst 4o (0.02 mmol, 2 mol%) and CH2Cl2 (4.0 mL). The resulting solution was stirred at r.t. for the indicated time. The solvent was then evaporated to give the crude product, which was directly purified by flash chromatography (n-pentane/EtOAc, 4:1 to 1:1) to provide the desired products 3a-t.

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:
Article; Gajulapalli, V. Pratap Reddy; Jafari, Ehsan; Kundu, Dipti S.; Mahajan, Suruchi; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter; Synthesis; vol. 49; 22; (2017); p. 4986 – 4995;,
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6341-92-0, name is 6-Chloroisatin, 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. SDS of cas: 6341-92-0

EXAMPLE 14a rac-6-Chloro-3-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-1,3-dihydro-indol-2-one 4-Bromo-1-methyl-1H-pyrazole was prepared according to the procedure of Dusza, J. P. et al., U.S. Pat. No. 6,511,974 B1, published Jan. 28, 2003. To a solution of 4-bromo-1-methyl-1H-pyrazole (0.98 g, 6.0 mmol) in tetrahydrofuran (10 mL) at -78 C. was added n-butyllithium (2.5 M in hexanes, 2.76 mL, 6.90 mmol) (Aldrich) dropwisely. The mixture was stirred at -78 C. for 10 minutes. To the obtained brownish solution was added a solution of 6-chloroisatin (0.5 g, 2.76 mmol) (Crescent) in tetrahydrofuran (5 mL). The reaction mixture was warmed up to room temperature and stirred at room temperature for 3 hours. The reaction was quenched with saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate three times. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by chromatography (ethyl acetate:dichloromethane, 1:1 V/V) to give rac-6-chloro-3-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-1,3-dihydro-indol-2-one as a yellow solid. (Yield 0.22 g, 30%).

The synthetic route of 6341-92-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Luk, Kim-Chun; So, Sung-Sau; Zhang, Jing; Zhang, Zhuming; US2006/293319; (2006); A1;,
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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. 919103-45-0, name is 6-Iodoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: indolines-derivatives

0.88 g (7.23 mmol) 4-N,N-dimethylaminopyridine and 44.6 mL (101.2 mmol) triethylamine are added successively to a suspension of 25.00 g (96.51 mmol) 6-iodo-1,3-dihydro-indol-2-one in 125.0 mL N,N-dimethylformamide. 27.81 g (197.8 mmol) benzoylchloride is added slowly at -10 C. to the reaction mixture and stirred for 2 h at -10 C. After complete conversion (HPLC, Method A) 48.0 mL 10 M sodium hydroxide solution is added and stirred 1 h at room temperature. Then 350 mL water, 150 mL toluene and 80 mL conc. hydrochloric acid are successively added. The resulting precipitate is filtered, washed with water and toluene and dried at 50 C. in vacuo.

The synthetic route of 919103-45-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ZAHN, Stephan Karl; SINI, Patrizia; BISTER, Bojan; US2014/18405; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, 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 5332-26-3, Recommanded Product: 5332-26-3

Salt (n-Bu4N)2[2-B10H9SH] (0.50g, 0.79mmol), N-(bromomethyl)phthalimide (0.19g, 0.84mmol), and cesium carbonate (0.26g, 0.39mmol) were placed in a 25-ml round-bottom flask and dissolved in 4ml DMF. The solution was heated to 40C in an argon atmosphere for 2h. After cooling to room temperature, a precipitate was removed by filtration and the solvent was distilled off on a rotary evaporator, and the dry residue was resuspended in 15ml of distilled water and allowed to stand in an ultrasonic bath to form a flocculated suspension. The precipitate was filtered off and washed with distilled water (2×10ml) and ethyl acetate (3×5 ml). Yield: 94%. Anal. calc. for C41H87B10N3O2S (%): C, 61.99; H, 11.04; N, 5.29; S, 4.04. Found (%): C, 61.72; H, 11.12; N, 5.15; S, 3.90. (0013) 1H NMR (CD3CN, delta, ppm): 7.74 (m, 4H, Ph), 4.24 (s, 2H, SCH2), 3.11 (m, 8H, n-Bu4N+), 1.61 (m, 8H, n-Bu4N+), 1.35 (m, 8H, n-Bu4N+), 0.96 (t, 12H, n-Bu4N+), 0.60-2.10 (m, 9H, B10H9). (0014) 13C NMR (CD3CN, delta, ppm): 168.3 (CO), 134.8, 133.4, 123.6 (Ph), 59.3 (n-Bu4N+), 41.5 (SCH2), 24.4 (n-Bu4N+), 20.3 (n-Bu4N +), 13.8 (n-Bu4N +). (0015) 11B-{1H} NMR (CD3CN, delta, ppm): -0.1 (d, 1B), -2.6 (d, 1B), -16.6 (s, 1B), -24.9 (d, 4B), -27.6 (d, 2B), -28.8 (d, 1B). (0016) IR (CCl4): 3467, 3087, 3070, 3042, 3030, 2978, 2950, 2875, 2500, 2477, 1773, 1702, 1614, 1455, 1439, 1401, 1372, 1318, 1190, 1158, 1107, 1083, 1010, 987, 941, 875,790, 711, 644, 605, 520cm-1.

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

Reference:
Article; Kubasov; Turishev; Golubev; Bykov, A.Yu.; Zhizhin, K.Yu.; Kuznetsov; Inorganica Chimica Acta; vol. 507; (2020);,
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Related Products of 3783-77-5, A common heterocyclic compound, 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione, molecular formula is C12H11NO3, 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.

To a cold slurry of 2-(3-oxobutyl)isoindoline-l,3-dione (2.12 g, 9.76 mmol) in MeOH (25 mL) at 0 C was added bromine (1.006 mL, 19.52 mmol). The reaction mixture was allowed to slowly warm to room temperature overnight. The reaction mixture was initially quenched with 10 M aq H2SO4 (15 mL). Once the intermediate methyl ether was no longer visible by LCMS, the reaction mixture was diluted with additional water (20 mL). The solid was collected, rinsed with water and air dried on the filter to afford 2-(4-bromo-3-oxobutyl)isoindoline-l,3-dione (2.13 g, 7.19 mmol, 73.7% yield) as a white solid. LC/MS (weak M+H): 295.9; LC retention time: 2.148 min (analytical HPLC Method N); NMR (400 MHz, CDCh): delta ppm 7.86 (dd, J=5.5, 3.1 Hz, 2H), 7.73 (dd, J=5.5, 3.1 Hz, 2H), 4.02 (t, J=7.2 Hz, 2H), 3.93 (s, 2H), 3.13 (t, J=7.2 Hz, 2H).

The synthetic route of 3783-77-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WROBLESKI, Stephen T.; BROWN, Gregory D.; LIN, Shuqun; DUAN, Jingwu; LU, Zhonghui; DHAR, T.G. Murali; XIAO, Hai-Yun; TEBBEN, Andrew J.; (103 pag.)WO2016/149437; (2016); 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 5332-26-3 as follows. Formula: C9H6BrNO2

Example 4 Diethyl phthalimidomethylphosphonate VII Triethyl phosphite (32 g, 192.59 mmol) was added to N-(bromomethyl)phthalimide III (46 g, 191.62 mmole) at room temperature and the reaction mixture was heated to 120 C. when vigorous reaction initiated by evolution of ethyl bromide gas. After 1 h at 120 C., the reaction mixture was allowed to cool down to room temperature and diluted with chloroform (250 ml). The mixture was washed with water (3*100 ml), brine (3*100 ml), dried over sodium sulfate and concentrated to furnish the phosphonate compound VII as a thick oil which is solidified on standing under vacuum; yield: 40 g; 70%. The crude material was carried over to the following step without further purification.

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HELVETICA INDUSTRIES (P) LIMITED; US2011/263870; (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 3339-73-9 as follows. Formula: C11H9NO4

Oxalyl chloride (5.8 ml; 66.7 mmol) is added to Pht-beta-Ala-OH (9.96 g; 44.5 mmol) dissolved in dichloromethane (120 ml) and 3 drops of dimethylformamide (DMF). The mixture is stirred for 3 hours at ambient temperature. After elimination of the solvent, the white solid is taken up in a 1:1 mixture of anhydrous tetrahydrofuran and acetonitrile (200 ml) then 49 ml of a 2 M solution of (trimethylsilyl) diazomethane in hexane (97.9 mmol) are added dropwise at 0 C. The solvents are eliminated after one night of stirring at 0 C. The pale yellow solid is then dissolved in dichloromethane (60 ml) and 12 ml of aqueous hydrobromic acid (48%) is added dropwise at 0 C. The mixture is stirred until the temperature reaches 15 C. and 50 ml of a saturated solution of sodium bicarbonate is added. The organic phase is washed with salt water then dried over sodium sulphate. Crystallization from diethyl ether allows a white solid to be obtained (11.39 g; yield=86%). [00199] NMR 1H (DMSO D6, 100 MHz, delta): 7.83 (s, 4H); 4.36 (s, 2H, CH2Br); 3.8 (t, 2H, J=7.1 Hz, NCH2); 2.98 (t, 2H, J=6.9 Hz, CH2CO).

According to the analysis of related databases, 3339-73-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Societe de Conseils de Recherches et d’Applications Scientifiques (S.C.R.A.S.); US6727269; (2004); B1;,
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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. 552330-86-6, name is 5-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., SDS of cas: 552330-86-6

Step 1: 5-mercaptoisoindolin-1-one (0569) (0570) Sodium 2-methylbutan-2-olate (31.2 g, 282.96 mmol) was added to 5-bromoisoindolin-1-one (30 g, 141.48 mmol) and phenylmethanethiol (35.1 g, 282.96 mmol) in DMF (300 mL) under nitrogen. The resulting mixture was stirred at 100 C. for 12 hours. The reaction mixture was quenched with water (300 mL), extracted with EtOAc (3×300 mL), the organic layer was dried over Na2SO4, filtered and evaporated to afford 5-(benzylthio)isoindolin-1-one (6.00 g, 16.61%) as a yellow solid. The water layer was acidified with 2M HCl and the mixture was extracted with EtOAc (3×150 mL). The organic layer was dried over Na2SO4, filtered and evaporated to dryness to afford 5-mercaptoisoindolin-1-one (15.00 g, 64.2%) as a solid. (0571) LC/MS: m/z=166 [M+H]+. 1H NMR (300 MHz, DMSO-d6) delta 4.32 (s, 2H), 5.88 (s, 1H), 7.37-7.40 (m, 1H), 7.49-7.54 (m, 2H), 8.45 (s, 1H).

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; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, 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 7477-63-6, SDS of cas: 7477-63-6

General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken in a 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, the reaction mixture was allowed to cool, quenched with water (10 mL) and extracted with DCM (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and volatiles were removed in vacuo. The crude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 percent ethyl acetate in petroleum ether to afford compound (4).

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, 7-Chloroisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Karmakar, Rajiv; Kayal, Utpal; Bhattacharya, Biswajit; Maiti, Gourhari; Tetrahedron Letters; vol. 55; 7; (2014); p. 1370 – 1372;,
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