Tag: M.W=200-300

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. 552330-86-6, name is 5-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromoisoindolin-1-one

Step 1: Methyl 3-((1-oxoisoindolin-5-yl)thio)propanoate (0451) (0452) A solution of 5-bromoisoindolin-1-one (10 g, 47.16 mmol) in dioxane (450 mL) was degassed before Xantphos (2.73 g, 4.72 mmol), DIPEA (9.88 mL, 56.59 mmol), Pd2(dba)3 (2.159 g, 2.36 mmol) and methyl 3-mercaptopropanoate (32.6 mL, 330.12 mmol) was added. The reaction was heated to 80 C. for 1 h. The reaction was concentrated in vacuo. Approximately half of the material was purified by flash chromatography eluting with 0-5% methanol in EtOAc to afford 4.69 g of product. Only half the material was purified this way because the crude material solidified part way through loading onto the column. The solidified material was triturated with methanol and 4.48 g of product was collected by filtration as a colorless solid. The mother liquor was concentrated in vacuo and purified by flash chromatography eluting with 0-5% methanol in EtOAc to afford 1.1 g product. This was combined with the material from the first column to give 10.27 g (86%) of the title compound. (0453) LC/MS: m/z=252 [M+H]+. 1H NMR (500 MHz, DMSO) delta 2.69 (t, 2H), 3.26 (t, 2H), 3.60 (s, 3H), 4.34 (s, 2H), 7.38 (d, 1H), 7.52 (s, 1H), 7.58 (d, 1H), 8.48 (s, 1H).

According to the analysis of related databases, 552330-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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Application of 18711-13-2, 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. 18711-13-2, name is 4,7-Dichloroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

In these schemes, ketone (4.0 equiv.) and a catalytic amount of diethylamine (10 drops) are added to a solution of substituted isatin (1.0 equiv.) in methanol (5 mL). The mixture is stirred at room temperature until starting material (substituted isatin) disappears completely. The resulting solution is concentrated and applied to flash chromatography eluting with hexane / ethyl acetate to afford pure product in quantitative yield. Further purification is done by recrystallization with hexane / ethyl acetate. An example compound synthesized by the above scheme includes: 4,7-Dichloro-3- hydroxy-3-[2-(4-methoxyphenyl-2-oxoethyl)]-l,3-dihydroindol-2-one: white solid; mp 149- 151 C; 1H NMR (DMSO, 400 MH 1 z) delta 10.93 (s, 1H), 7.86 (d, 2H, J = 9.2 Hz), 7.26 (d, 1H, J = 8.8 Hz), 6.98 (d, 2H, J= 8.8 Hz), 6.86 (d, 1H, J = 8.4 Hz), 6.39 (s, 1H), 4.31 (d, 1H, J= 18.0 Hz), 3.80 (s, 3H), 3.61 (d, 1H, J= 18.0 Hz).

The chemical industry reduces the impact on the environment during synthesis 4,7-Dichloroindoline-2,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; TOKALAS, INC.; VERNIER, Jean-michael; (82 pag.)WO2016/57698; (2016); 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. 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C9H6BrNO2

1-4.1 (15.0 g, 63 mmol) and hydrazine hydrate (30 mL, 618 mmol) are heated to 125 C for 72 h. To the cool reaction mixture DCM is added and extracted with water and 1 M HC1. The organic layer is dried over MgS04 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed in vacuo. The crystallized product is filtered by sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001 003.

The synthetic route of 667463-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRUNDL, Marc; MORSCHHAEUSER, Gerd; OOST, Thorsten; PAUTSCH, Alexander; WO2014/140078; (2014); A1;,
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Related Products of 667463-64-1, These common heterocyclic compound, 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-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.

Step 2: Synthesis of Intermediate I-4.2 [0294] I-4.1 (15.0 g, 63 mmol) and hydrazine hydrate (30 mL, 618 mmol) are heated to 125 C. for 72 h. To the cool reaction mixture DCM is added and extracted with water and 1 M HCl. The organic is layer is dried over MgSO4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed in vacuo. The crystallized product is filtered by sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001-003.

The synthetic route of 667463-64-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRUNDL, Marc; MORSCHHAEUSER, Gerd; OOST, Thorsten; PAUTSCH, Alexander; US2014/275114; (2014); A1;,
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Electric Literature of 169037-23-4, 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of isatin (0.15 g, 1 mmol), 5,5-dimethylcyclohexane-dione (0.14 g, 1 mmol), barbituric (0.13 g, 1 mmol) in gluconic acid aqueous solution (3 ml) was stirred at 100 C. The reaction progress was monitored by thin-layer chromatography. After completion of the reaction, the reaction mixture was cooled to room temperature. Then, the precipitated product was filtered and washed with water. The crude product was crystallized from ethanol to give 4a.

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, 5-(Trifluoromethoxy)indoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guo, Rui-Yun; Wang, Ping; Wang, Guo-Dong; Mo, Li-Ping; Zhang, Zhan-Hui; Tetrahedron; vol. 69; 8; (2013); p. 2056 – 2061;,
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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. 675109-26-9, name is 6-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Application In Synthesis of 6-Bromoisoindolin-1-one

To a solution of 6-bromo-2,3-dihydro-isoindol-l-one (1 equiv) in dry dioxan (0.1 M) were added bis(pinacolato)diboron (1.1 equiv), potassium acetate (3.5 equiv) and dppf (0.05 equiv). The reaction mixture was degassed with nitrogen for 20 minutes. PdCl2(dppf) (0.05 equiv) was added to the reaction mixture, which was degassed for a further 5 minutes. The reaction mixture was heated to 70C for 2 hours under nitrogen then heated to 1200C for 16 hours. The reaction mixture was partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc and the combined organic phases dried (MgSO4), filtered and concentrated in vacuo. The residue was sonicated in EtOAc, the suspension was filtered onto a sintered funnel and the collected grey solid was dried and used without further purification. 6-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-l-one: (82 % yield, 29 % purity, main impurity being the boronic acid 43 %) m/z (LC-MS, ESP): 519.5 [2M+H]+ R/T = 3.38 min

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; KUDOS PHARMACEUTICALS LIMITED; WO2008/23161; (2008); 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 2058-72-2 as follows. Quality Control of 5-Bromo-1-methylindoline-2,3-dione

General procedure: To a solution of isatin derivative 1a-r (1 mmol) in anhydrous toluene (1 mL, 1.0 M), MgSO4 (3 mmol) and NH3 solution 2M in methanol (2 mmol) were added. The reaction was stirred 8 hours at room temperature and then the mercapto-derivative 2a-c was added (1.1 mmol). The resulting mixture was stirred for further 30 minutes at the same temperature. The reaction was diluted with CH2Cl2 (5 mL) and then the solvent was removed under reduced pressure. The crude was purified by flash chromatography (FC)

According to the analysis of related databases, 2058-72-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rainoldi, Giulia; Begnini, Fabio; Silvani, Alessandra; Lesma, Giordano; Synlett; vol. 27; 20; (2016); p. 2831 – 2835;,
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These common heterocyclic compound, 20870-78-4, name is 5-Bromoindolin-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. Recommanded Product: 5-Bromoindolin-2-one

5-Bromo-1 ,3-dihydro-indol-2-one (Aldrich, 1.06 g, 5 mmol) was coupled with bis(pinacolato)diboron (Aldrich, 1.52 g, 6 mmol) catalyzed by PdCI2(dppf)2-CH2CI2 (Aldrich, 82 mg, 0.1 mmol) using KOAc (Aldrich, 0.98 g, 10 mmol) as base in dioxane (anhydrous, Aldrich, 50 ml_) at 8O0C for 10h. After being cooled down to ambient temperature, the mixture was diluted with EtOAc (50 ml_) and washed with brine (2 x 10 ml_). The organic solution was then concentrated under vacuum. The title compound was purified by chromatography (SiO2, hexane : EtOAc, 70:30, Rf. 0.5) as a solid (0.96 g, yield, 74%). 1H NMR (300 MHz, CDCI 3) delta 1.24 (s, 3 H), 1.28 EPO (s, 3 H), 1.34 (s, 6 H), 3.69 (s, 2 H), 6.86 (d, J=7.8 Hz, 1 H), 7.57 – 7.78 (m, 2 H) ppm. MS (DCI/NH3): 260 (M+H)+.

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

Reference:
Patent; ABBOTT LABORATORIES; WO2006/65233; (2006); A1;,
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Electric Literature of 101207-45-8, 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. 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 2-(4-methylbenzyl)isoindoline-l,3-dione (1 g, 3.8 mmol) and hydrazine hydrate (752 mg, 15 mmol, 730 pL) in MeOH (10 mL) was stirred at 20C for 3 hours. The mixture was concentrated in vacuo. The residue was purified by silica gel chromatography (0928) (dichloromethane:methanol (with 5% ammonia in water) = 0:1 to 5:1) to give p-tolylmethanamine (160 mg).

The chemical industry reduces the impact on the environment during synthesis 2-(4-Methylbenzyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; JUHL, Karsten; MARIGO, Mauro; VITAL, Paulo, Jorge, Vieira; JESSING, Mikkel; LANGGARD, Morten; RASMUSSEN, Lars, Kyhn; CLEMENTSON, Carl, Martin, Sebastian; (275 pag.)WO2019/115566; (2019); A1;,
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Reference of 552330-86-6, 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. 552330-86-6, name is 5-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step C: (Z)-5-Bromoisoindolin-1-one O-benzyl oxime: 5-Bromoisoindolin-1-one (3.00 g, 14.1 mmol) was suspended in 100 mL chloroform at 0 C. Triethyloxonium tetrafluoroborate (4.03 g, 21.2 mmol) was added in a single portion to the mixture and the suspension was stirred from 0 C. to ambient temperature over the 48 hours. The reaction was concentrated and the residue dissolved in 150 mL ethanol and cooled to 0 C. O-benyzyl hydroxylamine HCl (4.52 g, 28.3 mmol) and sodium carbonate (4.50 g, 42.4 mmol) were added, and the reaction was stirred from 0 C. to ambient temperature for 18 hours, then concentrated, diluted with ethyl acetate, washed with 10% citric acid, dried over sodium sulfate, filtered and concentrated to a solid. The solid was purified by silica gel chromatography with 100% dichloromethane (1.69 g, 37%).

The synthetic route of 5-Bromoisoindolin-1-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Miknis, Greg; Lyssikatos, Joseph P.; Laird, Ellen; Tarlton, Eugene; Buckmelter, Alexandre J.; Ren, Li; Rast, Bryson; Schlacter, Stephen T.; Wenglowsky, Steven Mark; US2007/49603; (2007); A1;,
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