Month: May 2021

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. 317-20-4, name is 7-Fluoroisatin, A new synthetic method of this compound is introduced below., Formula: C8H4FNO2

198 mg (1.2 mmol) 7-fluoroisatin, 144.1 mg (1.44 mmol) 2,4-pentanedione, 50 mL THF and 5 mL DMF as solvent, 1 mL H2O2, and 14.5 mg ZnCl2 as catalyst were added to a 100 mL round flask. The mixture was stirred and heated at 85 C. for 12 hours. The reaction was monitored with TLC. When TLC indicated that reaction was complete, heating was removed. The reaction mixture was concentrated, filtered, and washed with THF to obtain 175.5 mg desired product (compound 9), a yield of 59.2%. 1H-NMR (300 MHz, DMSO-d6) delta (ppm): 10.95 (1H, s), 7.59 (1H, d), 6.89 (1H, d), 6.75 (1H, t), 2.38 (3H, s), 2.24 (3H, s); 13C-NMR (75 MHz, DMSO-d6) delta (ppm): 164.2, 161.1, 153.6, 148.8, 129.9, 126.3, 117.4, 109.9, 106.3, 92.5, 23.9, 11.2; MS (ESI) for (M+H)+: 248.1.

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; SHAANXI UNIVERSITY OF SCIENCE AND TECHNOLOGY; Liang, Chengyuan; Tian, Danni; Jia, Minyi; (11 pag.)US10035808; (2018); B1;,
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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. 61-70-1, name is 1-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 1-Methylindolin-2-one

To a 50 ml single-flask containing 10 ml water and 10 ml ethanol was added sodium hydroxide (10 mmol, 0.4 g). The reaction mixture was stirred until the solid dissolved. Then cooled to room temperature, indole-2-one (5.0 mmol) and benzaldehyde (5.5 mmol) was added. The reaction was stirred at room temperature for 2.0 hours. After addition of water (25 ml), the mixture was filtered and washed with water to give the desired products, yield: 85%.

The synthetic route of 61-70-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Lihong; Li, Zhanshan; Lu, Lianhong; Zhang, Wei; Tetrahedron; vol. 68; 5; (2012); p. 1483 – 1491;,
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Some common heterocyclic compound, 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, molecular formula is C8H4KNO2, 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. COA of Formula: C8H4KNO2

Potassium phthalimide (18.62 g, 0.10 mol) and tetrabutylammoniumbromide (TBAB, 5.00 g) were added to a solutionof 1,4-dibromobutane (35.5 mL, 0.30mol) in N, N-Dimethylformamide (DMF, 240 mL) at room temperature and then the mixture was stirred at 78 C for 6 h. After the completion of the reaction (monitored by TLC analysis), the mixture was filtered, and washed with DMF (20 mL × 2).The filtrate was evaporated under vacuum to removed DMF,the residual liquid was poured into ice-water bath, immediately a large amount of white solid generated. The white solid was collected by filtration, washed on the filter withwater and dried in vacuum. The crude residue was purifiedby recrystallization from methanol to afford pure N-(4-Bromobutyl) phthalimide 2 (23.60 g, 84%, m.p. 79-81oC aswhite solid. 1H NMR (CDCl3, 400 MHz), delta: 1.82-1.95 (m,4H, C13H, C14H), 3.45 (t, J=6.3 Hz, 2H, C15H), 3.73 (t,J=6.6 Hz, 2H, C16H), 7.27-7.74 (m, 2H, C3H, C6H), 7.83-7.86 (m, 2H, C1H, C2H); 13C NMR (CDCl3, 100 MHz), delta:27.3 (C13), 29.9 (C14), 32.8 (C15), 37.0 (C12), 123.3 (C3,C6), 132.1 (C4, C5), 134.0 (C1, C2), 168.4 (C7, C9). KunHu has reported the same compound in 2013 [17], the NMRcharacterization in the literature is described as follows: 1HNMR (CDCl 3, 500 MHz): d 1.84-1.94 (m, 4H), 3.45 (t,2H, J = 6.0 Hz), 3.73 (t, 2H, J = 6.5 Hz), 7.73 (dd, 2H, J =3.0, 5.5 Hz), 7.85 (dd, 2H, J = 3.0, 5.0 Hz); 13 C NMR(CDCl 3, 125 MHz): d 27.27, 29.89, 32.73, 36.99, 123.27,132.11, 133.99, 168.36.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1074-82-4, its application will become more common.

Reference:
Article; Shao, Yan-Dong; Song, Huang-Wang; Feng, Wen; Wang, Xiang-Hui; Shi, Zai-Feng; Wu, Lu-Yong; Chen, Guang-Ying; Lin, Qiang; Letters in Organic Chemistry; vol. 15; 3; (2018); p. 206 – 213;,
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Related Products of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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 1. Dimethyl (phthalimidomethyl)phosphonate (ii). A mixture of N-(bromomethyl) phthalimide (i) (10.43 g, 43.46 mmol) and trimethyl phosphite (5.93 g, 47.80 mmol) was heated at reflux in xylene (20 mL) for 6 h. The reaction mixture was then cooled to room temperature and concentrated. Crystallization from CHCl3hexane gave (ii) (7.60 g, 65%) as a white solid: 1H NMR (300 MHz, CDCl3) deltaH 3.84 (d, JH,P=10.8 Hz, 6 H), 4.12 (d, J=11.4 Hz, 2 H), 7.76 (m, 2 H), 7.87 (m, 2 H).

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; MethylGene, Inc.; US2004/82546; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 6941-75-9, 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. 6941-75-9 name is 5-Bromoisoindoline-1,3-dione, 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.

General procedure: The mixture of 4-bromophthalimide (225 mg, 1 mmol), 4-RPhSH(3 mmol), K2CO3 (136 mg, 1 mmol) and CuI (10 mg) was added to DMF (10 mL). The solution was heated at 130 C for 6 h under the protection of nitrogen. After cooled, water (30 mL) was added and the precipitation was filtered, washed with water. The product was purified by column chromatography on silica gel using dichloromethane/acetone (60:1).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisoindoline-1,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Li, Xiangqian; Liang, Xiaomeng; Song, Ting; Su, Pengchen; Zhang, Zhichao; Bioorganic and Medicinal Chemistry; vol. 22; 21; (2014); p. 5738 – 5746;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 16800-68-3, name is 1-Acetylindolin-3-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 16800-68-3

Step 1 : 2-(1-Acetyl-1 H-indol-S-yO-S-hydroxycyclopent^-enone. 1-Acetyl-1 ,2-dihydro-indol-3-one (7.0 g) is suspended in acetic acid (80 ml) and 1 ,3-cyclopentane-dione (3.92 g) is added. The reaction mixture is stirred for 20 min and triethylamine (5.56 ml) is added. The mixture is partitioned into 4 microwave vials and each portion is heated for 2 h at 1850C in the microwave. The reaction mixtures are recombined and concentrated in vacuo. The residue is treated with 2M methanolic hydrochloride solution (20 ml) and further methanol (5 ml) is added, until complete dissolution occurred. The solution is again concentrated in vacuo and the crude product is purified by flash chromatography (silica gel, eluting with ethyl acetate). The product is crystallized from ether / ethyl acetate 9:1 (v/v) to give 6.8 g (66%) of 2-(1-acetyl-1/-/-indol-3-yl)-3-hydroxycyclopent-2-enone.1H-NMR (200 MHz, CDCI3); delta = 2.31 (s, 3H), 2.55-2.82 (m, 5H), 7.19-7.59 (m, 4H), 8.43 (d, J = 7.5 Hz, 1 H).

The synthetic route of 16800-68-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NYCOMED GMBH; BARTELS, Bjoern; WEINBRENNER, Steffen; MARX, Degenhard; DIEFENBACH, Joerg; DUNKERN, Torsten; MENGE, Wiro M.P.B.; CHRISTIAANS, Johannes A. M.; WO2010/15587; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5332-26-3, The chemical industry reduces the impact on the environment during synthesis 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

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; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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Synthetic Route of 18711-13-2, The chemical industry reduces the impact on the environment during synthesis 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: (The reagents were purchased fromAdamas and used without further purification.) A dry 3-mL flask was chargedwith relevant isatin 5 (0.3 mmol), tert-butyl 2-aminoacetate hydrochloride 7(0.3 mmol) and benzophenone imine 8 (0.36 mmol). The reaction mixture wasstirred at room temperature for the corresponding time. After the completionof the reaction, the reaction mixture was directly purified by silica gelchromatography (ethyl acetate/petroleum ether = 1:4) to give product 6. Asolution of 6 in EA/TFA (10:1) was stirred in a 10-mL flask under roomtemperature for 3 h. The solvent was removed under vacuum. The residue wasrecrystallized in diethyl ether/petroleum ether to give product 9.

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, 4,7-Dichloroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Huang, Huang; Xu, Yong; Mao, Fei; Zhu, Jin; Jiang, Hualiang; Li, Jian; Tetrahedron Letters; vol. 56; 4; (2015); p. 586 – 589;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 337536-15-9, name is 4-Bromoisoindolin-1-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. category: indolines-derivatives

Example 6 4-{5-[3-fluoro-5-(trifluoromethoxy)phenyl]-1-(pyridine-3-yl)-1H-pyrazole-3-yl}-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-1-one Step 4 [0553] In three parallel mixtures, each of three 100 mg (0.25 mmol) portions of the product from step 3 is dissolved in 5 ml dioxane in each case and each is combined with 76 mg (0.30 mmol) of bis-pinakolato-diboron, 73 mg (0.75 mmol) potassium acetate and 12 mg (0.017 mmol) [1,1-bis-(diphenyl-phosphino)ferrocene]-dichloropalladium dichloromethane complex. The reaction mixtures are stirred for 1 h in the microwave at 120 C. and cooled to RT, then combined with 50 mg (0.30 mmol) of the compound from example 22A, 250 mul (2 N in water, 0.50 mmol) sodium carbonate solution and 10 mg (0.013 mmol) [1,1-bis-(diphenylphosphino)ferrocene]-dichloropalladium dichloromethane complex and stirred for 2 h at 120 C. The reaction mixtures are combined. The suspension is diluted in a small amount of acetonitrile, filtered through a Millipore filter and separated by preparative HPLC (solvent: acetonitrile/water gradient). Once the resulting solid has crystallized out of the acetonitrile, this produces 174 mg (51% of theoretical yield) of the title compound. Example 7 4-{5-[3-fluoro-5-(trifluoromethoxy)phenyl]-1-(pyridine-3-yl)-1H-pyrazole-3-yl}-2,3-dihydro-1H-isoindole-1-one [0556] title compound is performed starting from 100 mg (0.25 mmol) of the product from step 3 of the compound from example 6 in a manner analogous to step 4 from example 6, whereby instead of the compound from example 22A, 4-bromo-2,3-dihydroisoindole-1-on (63 mg, 0.30 mmol) is used. This produces 64 mg (56% of theoretical yield) of the title compound. [0558] 1H-NMR (400 MHz, DMSO-d6): delta=4.73 (s, 2H), 7.12 (s, 1H), 7.43 (dt, 1H), 7.48-7.58 (m, 3H), 7.64 (t, 1H), 7.72 (d, 1H), 7.85-7.91 (m, 1H), 8.16 (d, 1H), 8.64 (d, 1H), 8.67 (d, 1H), 8.75 (s, 1H). [0559] LC-MS (Method 3): Rt=1.07 min; MS (ESIpos): m/z=455 [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 337536-15-9, its application will become more common.

Reference:
Patent; AICURIS GMBH & CO. KG; Wildum, Steffen; Klenke, Burkhard; Wendt, Astrid; US2015/203500; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

A mixture of the appropriate amine (1 mmol) and the appropriate benzyl bromide (1 mmol) in DMF (0.5 M) was stirred at room temperature up to 100 C until completion of the reaction (up to5 days). The reaction mixture was either diluted with EtOAc and the resultant precipitate filtered to give pure product or quenched with sat. NaHCO3 and extracted with EtOAc. Crude material was purified either by automated flash chromatography (EtOAc:hexanes mixture) or by preparative HPLC to give the desired compound in 10-50% yield; ?H NIVIR (400 MHz, DMSO-d6)10.80 (s, 1H), 7.55 (dd, J= 13.2, 8.2 Hz, 3H), 7.48 – 7.40 (m, 1H), 7.15 (t, J 4.7 Hz, 1H), 7.03 (d, J 2.1 Hz, 1H), 6.97 (dd, J 8.4, 2.1 Hz, 1H), 4.53 (d, J= 4.6 Hz, 2H). ?3C NIVIR (101 1VIHz, DMSO) 170.07, 169.81, 154.14, 136.18, 135.86, 133.44, 131.11, 129.23, 125.00, 118.91, 115.96, 105.49, 43.32.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Aminoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; THE CENTRE FOR DRUG RESEARCH AND DEVELOPMENT; THE UNIVERSITY OF BRITISH COLUMBIA; ROBERGE, Michel; BARADARAN-HERAVI, Alireza; BALGI, Aruna D.; ZIMMERMANN, Carla D.; KRAUSE, Alexandra; PFEIFER, Thomas Arthur; JAQUITH, James Brian; TAN, Jason Samuel; SHIDMOOSSAVEE, Fahimeh S.; ARNS, Stephen Paul; BAUDELET, Davy Jeremy; (354 pag.)WO2017/49409; (2017); A1;,
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