Month: July 2021

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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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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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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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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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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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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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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Some common heterocyclic compound, 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, molecular formula is C11H9NO3, 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: (R)-(-)-N-(2,3-Epoxypropyl)phthalimide

General procedure: Compounds 2-5 were synthesized using a modified procedure originally reported by Roehrig et al.28 To a cooled solution of (R)-(-)-N-(2,3-epoxypropyl)phthalimide 1 (102 mg, 0.50 mmol) in 10 mL of 2-propanol, amine or aminoalcohol (0.6 mmol, 1.2 equiv) in 10 mL of 2-propanol was added at 0 C and stirred for 1 h. It was then refluxed for 8 h. After the completion of the reaction, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silica gel (CHCl3/MeOH 1:20 as eluent) to afford 2-5 as white crystals.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 181140-34-1, its application will become more common.

Reference:
Article; Bozkurt, Selahattin; Durmaz, Mustafa; Naziroglu, Hayriye Nevin; Yilmaz, Mustafa; Sirit, Abdulkadir; Tetrahedron Asymmetry; vol. 22; 5; (2011); p. 541 – 549;,
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Synthetic Route of 1055412-47-9, The chemical industry reduces the impact on the environment during synthesis 1055412-47-9, name is su-5614, I believe this compound will play a more active role in future production and life.

A suspension of 5-chloro-3-(1H-pyrrol-2-yl-methylene)-1,3-dihydro-indol-2-one (260 mg, 0.96 mmol), piperidine (95 muL, 0.96 mmol) and paraformaldehyde (43 mg, 1.44 mmol) in 5 mL of dioxane and 5 mL of EtOH was heated to 80 C. for 15 h. The resulting solution was cooled to room temperature followed by cooling to -20 C. for 1 h. The solid which formed was collected by filtration and rinsed with EtOH (previously cooled to -20 C.). The solid collected was dried under vacuum to give the title compound (180 mg, 51%) as a yellow-orange 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, su-5614, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Allergan, Inc.; US6699863; (2004); B1;,
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Application of 3891-07-4,Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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.

Under nitrogen, to a cooled (0 C) solution of Ph3P (9.44 g, 36 mmol) in dry THF (60 mL), diisopropylazodicarboxylate (DIAD) (7.08 mL, 36 mmol) was added dropwise at stirring. The suspension obtained was stirred for 30 min and then a suspension of calixarene 9 (1:1 p-xylene complex, 6.40 g, 6 mmol) and 2-hydroxyethylpthalimide (6.88 g, 36 mmol) in THF (200 mL) was added dropwise. The stirring was continued for 1 h at low temperature and then for 24 h at room temperature. The reaction mixture (clear solution) was concentrated in vacuo to an oil, which was triturated with methanol. The solid formed was separated, washed with methanol and dried. Yield 89% (6.98 g, white powder). Mp 234-236 C (decomp.). 1H NMR (400 MHz, CDCl3) delta 7.93 (4H, m, ArHPht), 7.70 (4H, m, ArHPht), 6.96 (4H, s, ArH), 6.67 (4H, s, ArH), 6.65 (2H, s, OH), 4.44 (4H, t, J=6.6 Hz, NCH2), 4.24 (4H, t, J=6.6 Hz, OCH2), 4.18 (4H, d, J=2.9 Hz, ArCH2Ar), 3.25 (4H, d, J=12.9 Hz, ArCH2Ar), 2.10-1.35 (60H, m, HAd). 13C NMR (100 MHz, CDCl3) delta 168.10 (CO), 150.47, 149.01, 146.87, 141.49 (CAr), 133.83 (CHAr,Pht), 132.13, 132.09 (CAr), 127.72 (CAr,Pht), 124.96, 124.26 (CHAr), 123.22 (CHAr,Pht), 71.79 (OCH2), 43.70, 42.74 (CAd), 37.47 (NCH2), 36.91, 36.61 (CAd), 35.29, 35.26 (CAd), 31.11 (ArCH2Ar), 29.08, 28.76 (CHAd). FD-MS: m/z 1308.5 [M+H]+; C88H94N2O8·H (1308.7).

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

Reference:
Article; Vatsouro, Ivan; Serebryannikova, Alina; Wang, Leyong; Hubscher-Bruder, Veronique; Shokova, Elvira; Bolte, Michael; Arnaud-Neu, Franoise; Boehmer, Volker; Kovalev, Vladimir; Tetrahedron; vol. 67; 42; (2011); p. 8092 – 8101;,
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