Category: indolines-derivatives

Electric Literature of 675109-45-2, A common heterocyclic compound, 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, molecular formula is C8H8N2O, 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: 6-Bromo-4-chloroquinoline (1.0 equiv.) and 3,4,5-trimethoxyaniline (1.1 equiv.) were suspended in ethanol (10 mL) and refluxed for 18 h. The crude mixture was purified by flash chromatography using EtOAc:hexane followed by 1-5% methanol in EtOAc, solvent was removed under reduced pressure to afford the desired product (1, 8-11, 13-31, and 33-43).

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; Asquith, Christopher R.M.; Bennett, James M.; Su, Lianyong; Laitinen, Tuomo; Elkins, Jonathan M.; Pickett, Julie E.; Wells, Carrow I.; Li, Zengbiao; Willson, Timothy M.; Zuercher, William J.; Molecules; vol. 24; 22; (2019);,
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Reference of 132898-96-5,Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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: 5-{[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-1H-indole-2,3-dione To a cold suspension of 2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride (5.28 g, 21.5 mmol) in a 1:1 mixture of THF:CHCl3 (254 mL) was added drop-wise via syringe pump a solution of (S)-(+)-2-(methoxymethyl)-pyrrolidine (3.45 mL, 28.0 mmol, 1.3 eq) (Aldrich) and N,N-diisopropylethylamine (7.49 mL, 43 mmol, 2 eq) in CHCl3 (42 mL) over a period of 70 minutes under a dry N2 atmosphere with cooling in an ice bath. After stirring an additional 20 minutes the mixture was concentrated. The residue was flash chromatographed (Biotage KP silica gel, 98/2 CH2Cl2/CH3OH) to give the title compound as a dark greenish-yellow foam (6.48 g. 93% yield). NMR (400 MHz, DMSO-d6): consistent MS: (API-ES-) m/z 323[M-H].

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

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
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Related Products of 480-91-1, A common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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.

Example 65ATert-Butyl(+/-)-cyclopentyl{4-[(1-oxo-1,3-dihydro-2H-isoindol-2-yl)methyl]phenyl}acetate At 0 C., 611.3 mg (15.3 mmol, 60%) of sodium hydride were added to 2.035 g (15.3 mmol) of 1-oxoindoline in 12 ml of DMF. The mixture was stirred for 25 min, and 6.0 g (12.7 mmol, about 75% pure) of tert-butyl(+/-)-[4-(bromomethyl)phenyl](cyclopentyl)acetate were then added at 0 C. The reaction mixture was stirred for a further 4 h while slowly warming to RT, water was then added and the mixture was extracted twice with dichloromethane. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. In an ultrasonic bath, the crude product was treated with diethyl ether, and the solid was filtered off with suction and dried. This gave 3.40 g (65.2% of theory) of the target compound.LC-MS (Method 4): Rt=1.05 min; m/z=406 (M+H)+.1H-NMR (400 MHz, DMSO-d6): delta=7.73 (d, 1H), 7.63-7.48 (m, 3H), 7.31 (d, 2H), 7.22 (d, 2H), 4.71 (s, 2H), 4.39 (s, 2H), 3.18 (d, 1H), 2.47 (m, 1H), 1.82 (m, 1H), 1.65-1.36 (m, 4H), 1.35 (s, 9H), 1.30-1.20 (m, 2H), 0.95 (m, 1H).

The synthetic route of 480-91-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; US2012/28971; (2012); 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. 919103-45-0, name is 6-Iodoindolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Iodoindolin-2-one

Step 4: N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-(2-oxo-2,3-dihydro-1H-indol-6-ylsulfanyl)-benzamide CuI (40 mg, 0.05 mmol), potassium carbonate (1.66 g, 12 mmol), 6-iodooxindole (as prepared in Preparation 1; 0.5 g, 1.93 mmol) and N-(2,5-Dimethyl-2H-pyrazol-3-yl)-2-mercapto-benzamide (as prepared in step 3 above; 0.477 g, 1.93 mmol) were added to a dry schlenk tube. The tube was evacuated and refilled with Ar(g) (3 times). Isopropanol (3.0 mL) and ethylene glycol (0.250 mL) were injected into the schlenk tube. The schlenk tube was sealed with a teflon valve and was heated to 80 C. and stirred for over 24 hours. Subsequently the reaction mixture was allowed to reach room temperature then diluted with EtOAc (20 mL) and water (10 mL). The mixture was acidified with 1 M HCl(aq) and the organics were separated and set aside. The aqueous phase was washed with EtOAc (2×20 mL). The organic layers were combined, dried over silica gel, filtered and concentrated in vacuo affording a yellow solid. The solid was then purified via flash silica gel chromatography (gradient eluant 10 to 40% EtOAc in Hexanes) affording the title compound as a pale yellow solid (0.379 g, 1.01 mmol, 52% yield).

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

Reference:
Patent; Allergan, Inc.; US2007/15748; (2007); A1;,
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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. 60434-13-1, name is 5-Chloro-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H6ClNO2

General procedure: General procedure forthe preparation of oxazolo[5,4-b]quinoline- fused spirooxindoles 4a-t: A reaction of isatin(1 mmol),beta-diketone (1 mmol) and5-amino-3-methylisoxazole (1 mmol) were mixed and irradiated in a closed vesselin the absence of any solvent in a Synthos 3000 microwave reactor at 700 W, 14 bar,and 110 C for 10 min. The reaction was monitored by TLC. Then, thereaction mixture was filtered hot and the resulting solid products were washed with ethanol, dried in air and recrystallized from ethanol.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 60434-13-1.

Reference:
Article; Yuvaraj, Panneerselvam; Manivannan, Karthikeyan; Reddy, Boreddy S.R.; Tetrahedron Letters; vol. 56; 1; (2015); p. 78 – 81;,
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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. 603-62-3, name is 3-Nitrophthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 3-Nitrophthalimide

To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspension was stirred at 0 C for 3 hrs, and then heated to 30 C for 3 hrs. To the solution, was added HC1 (100 mL, 6N). The resulting suspension was cooled to 0 C for 1 hr. The suspension was filtered and washed with cold water (2 x 10 mL) to give 3- nitro-phthalamic acid as a white solid (24.6 g, 90% yield): ?H NMR (DMSO-d6) 5 7.69 (brs, 1H, NHJ]), 7.74 (t, J= 8 Hz, 1H, Ar), 7.92 (dd, J= 1, 8 Hz, 1H, Ar), 8.13 (dd, J= 1, 8Hz, 1H, Ar), 8.15 (brs, 1H, NHJ]), 13.59 (s, 1H, 01]); ?3C NIVIR (DMSO-d6) 5125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

The synthetic route of 603-62-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELGENE CORPORATION; HUANG, Lianfeng; ZOU, Daozhong; (177 pag.)WO2018/165142; (2018); A1;,
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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. 341988-36-1, name is Methyl indoline-6-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 341988-36-1

Step 2: A solution of 2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (1.34 g, 7.6 mmol) in dichloromethane (66 ml) and pyridine (1.6 ml) was treated with 5-chloro-2-methoxy-benzenesulfonyl chloride (1.83 g, 7.6 mmol, 1 equiv.). The mixture was stirred at room temperature overnight, then diluted with dichloromethane and washed with water. The organic phase was dried with Na2SO4 and evaporated. The residue was purified by flash chromatography (heptane/ethyl acetate gradient), yielding 1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester, 2.2 g (77percent yield). MS (ISP): m/e=382.1 (M+H+.), deltaH (300 MHz; CDCl3) 7.99 (1H, d), 7.93 (1H, s), 7.61 (1H, d), 7.37 (1H, dd), 7.11 (1H, d), 6.77 (1H, d), 4.04 (2H, t), 3.83 (3H, s), 3.56 (3H, s), 3.02 (2H, t).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 341988-36-1.

Reference:
Patent; Ackermann, Jean; Bleicher, Konrad; Ceccarelli Grenz, Simona M.; Chomienne, Odile; Mattei, Patrizio; Schulz-Gasch, Tanja; US2007/60567; (2007); 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. 446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione

4 (^ (0.09111001) Compound 7,36.7840% (0.42111001) of the methylamine solution was added to methanol 2L of the three-necked flask, The temperature of the system was increased to 65 C for 1 h, and 62.2 g (0.49 mil) of oxalic acid and 200 mL of methanol was added dropwise to the system until the pH of the system was stopped at 2-3, At this point the system has a large amount of solid precipitation, the system heated reflux lh, cooled to room temperature, filtration, filter cake with methanol, 50 C vacuum drying to get 34.2g compound 8 (95.1%), 250 C above decomposition

The synthetic route of 446292-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Sibeiyuan Pharmaceutical Technology Co., Ltd.; Liu Xiaohong; Song Xingchang; Zhang Aihua; Wu Yundeng; (11 pag.)CN103951661; (2017); B;,
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Synthetic Route of 20780-72-7, The chemical industry reduces the impact on the environment during synthesis 20780-72-7, name is 4-Bromoisatin, I believe this compound will play a more active role in future production and life.

To a solution of 4-bromoisatin (8.94 g, 39.5 mmol) in anhydrous N, N- dimethylformamide (100 ml_) was added sodium hydride (3.34 g, 86.9 mmol, 60percent dispersion in mineral oil) in portions at 0 0C. The brown reaction mixture was stirred for 30 min followed by the addition of a solution of 2-(bromomethyl)pyridine hydrobromide (10.0 g, 39.5 mmol) neutralized with sodium hydride (1.52 g, 39.5 mmol, 60percent dispersion in mineral oil) in Lambda/,Lambda/-dimethylformamide at 0 0C. The reaction mixture was stirred for 16 h and quenched with water (100 ml_). The reaction mixture was extracted with diethyl ether (3 x 100 mL) and the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined organic layers was washed with water (5 x 200 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was triturated with ether to afford the title compound (10.6 g,85percent) as a brown solid: 1H NMR (300 MHz, DMSO-d6) delta 8.53 (d, 1 H), 7.67 (t, 1 H), 7.30 (t, 2H), 7.25-7.19 (m, 2H), 6.94 (d, 1H), 5.04 (s, 2H); 13C NMR (75 MHz, DMSO-d6) delta 180.5, 157.3, 154.2, 152.3, 149.5, 138.4, 137.5, 128.6, 123.3, 122.3, 121.5, 116.4, 110.3, 45.8.

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, 4-Bromoisatin, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; XENON PHARMACEUTICALS INC.; WO2006/113864; (2006); A2;,
Indoline – Wikipedia,
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Application of 59-48-3,Some common heterocyclic compound, 59-48-3, name is Indolin-2-one, molecular formula is C8H7NO, 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.

1,3-Dihydro-indol-2-one 30a (20.0 g, 150 mmol) was dissolved in sulfuric acid (100 ml, 98%) in an ice-water bath under stirring, and added dropwise with nitric acid (10 ml, 65%-68%) while maintaining the temperature below 0C. Upon completion of the addition, the mixture was stirred for 1 hour at 0C. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was added with ice and filtered after ice-out. The filter cake was washed with water (20 ml×”)), and the resulting solid was recrystallized to obtain the title compound 5-nitro -indol-2-one 30b (25.3 g, yield 92.4%) as an orange solid. MS m/z (ESI): 177.3[M-1]

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

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2157093; (2010); A1;,
Indoline – Wikipedia,
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