Author: Jessica.F

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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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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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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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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Application of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-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.

Example 25: Synthesis of dimethyl-(6-phenylaminomethyl-phthalazin-l-yl)-amine; 5-Bromo-3-hydroxy-2,3-dihydro-isoindol-l-oneA mixture of zinc powder (8.68 g, 132.7 mmol), copper (II) sulfate pentahydrate(0.11 g, 0.44 mmol) and aqueous sodium hydroxide (135 mL, 2M solution) were cooled to 0 0C. Bromophthalimide (25 g, 110.6 mmol) was added in portions over 30 minutes, maintaining the temperature at 0 0C. The reaction was stirred at 0 0C for 30 minutes, and at room temperature for 3 h. The reaction was filtered, neutralized to pH 7 with concentrated HCl, diluted with EtOH, and then extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the desired compound (15.75 g, 63 %) as a colourless solid.

Statistics shows that 5-Bromoisoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 6941-75-9.

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61108; (2008); A2;,
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These common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, 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. Formula: C8H6N2O3

General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

The synthetic route of 5-Nitroindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wei, Wen-Ting; Ying, Wei-Wei; Zhu, Wen-Ming; Wu, Yi; Huang, Yi-Ling; Cao, Yi-Qi; Wang, Yi-Ning; Liang, Hongze; Synlett; vol. 28; 17; (2017); p. 2307 – 2310;,
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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. 21857-45-4, name is 5-Methoxyindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 21857-45-4

Weigh 5-methoxy indole (0.35 g, 2.35 mmol) in a two-necked flask,Add DCM (7mL) to dissolve,After adding DIPEA (0.36 g, 2.82 mmol) under ice bath conditions,Allyl chloride (0.23 g, 2.59 mmol) was added dropwise,After the addition is complete, the reaction is continued under ice bath conditions.Check the progress of the reaction through the TLC point plate,About 5 hours after the reaction is completed,After processing,DCM (20 mL) was added to dilute the reaction solution.Wash with saturated sodium bicarbonate solution (20 mL),Extract the sodium bicarbonate solution layer with DCM (10 mL×3).Dry with anhydrous magnesium sulfateconcentrate,Purification by column chromatographyThe target compound (0.28 g, yield 58.7%) was obtained.

The synthetic route of 21857-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin Binjiang Pharmaceutical Research And Development Co., Ltd.; Tian Hongqi; Huang Gongchao; Cheng Ying; (48 pag.)CN107793413; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, 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 20870-90-0, Quality Control of 5-Bromo-1-methyl-2-oxoindoline

General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Wei, Wen-Ting; Ying, Wei-Wei; Zhu, Wen-Ming; Wu, Yi; Huang, Yi-Ling; Cao, Yi-Qi; Wang, Yi-Ning; Liang, Hongze; Synlett; vol. 28; 17; (2017); p. 2307 – 2310;,
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. 3485-84-5, name is N-Vinylphthalimide, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3485-84-5

N- Vinyl phthalimide (0.100 g, 0.577 mol) was treated with 4N HCl/dioxane (0.433 mL, 1.73 mmol) at 25 C. After 3 hours the reaction mixture was concentrated under reduced pressure to provide an off white solid (112 g, 93% yield). 1H NMR (400 MHz, CDC13) delta 7.95-7.89 (m, 2H), 7.83-7.77 (m, 2H), 6.32 (q, J=6.8 Hz, 1H), 2.19 (d, J=6.8 Hz, 2H), LC tr=3.05 minutes (C-18 column, 5 to 95% acetonitrile/water over 6 minutes at 1.7 mL/min with detection 254 nm, at 23 C).

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 3485-84-5.

Reference:
Patent; EUCLISES PHARMACEUTICALS, INC.; MARTINEZ, Eduardo, J.; TALLEY, John, J.; JEROME, Kevin, D.; BOEHM, Terri, L.; WO2014/12074; (2014); A2;,
Indoline – Wikipedia,
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550-44-7, name is 2-Methylisoindoline-1,3-dione, 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. Product Details of 550-44-7

(1) Refer to Figure 2 to determine the microchannel reactor connection mode, remove the preheating zone module, the channel type is cylindrical straight channel and circular microchannel structure, the number of microchannel mixed reaction modules is determined according to the flow rate and residence time.The N-methylphthalimide-concentrated sulfuric acid solution was regarded as the raw material A, the concentrated nitric acid solution was regarded as the raw material B, and the two materials were injected into the reaction zone through the metering pump at a flow rate of 10 ml/min and 25 ml/min, respectively. In the mixed residence reaction, the molar ratio of concentrated nitric acid to substrate is 1.2:1, the mass ratio of substrate to concentrated sulfuric acid is 1:2, and the microchannel reactor of Fig. 2 is used to control the temperature of 60 C, residence time. 180s, the reaction solution was quantitatively collected, washed with ice water, washed with water, filtered, and dried to obtain N-methyl-4-nitrophthalimide nitrated product, HPLC content analysis (normalized) 97%, yield 96 %.

The synthetic route of 550-44-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Zhejiang Wanfeng Chemical Co., Ltd.; Liu Tao; Yao Chenhua; Yu Xingying; Yu Xiaotian; (11 pag.)CN109305933; (2019); A;,
Indoline – Wikipedia,
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