Author: Jessica.F

Electric Literature of 111992-61-1, 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. 111992-61-1, name is 2-(3-Bromo-2,2-dimethylpropyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

Step 3. A suspension of 3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (400 mg, 1.3 mmol, 1.00 equiv), 2-(3-bromo-2,2-dimethylpropyl)-2,3-dihydro-1H-isoindole-1,3-dione (570 mg, 1.95 mmol, 1.50 equiv) and cesium carbonate (847 mg, 2.60 mmol, 2.00 equiv) in NMP (50 mL) was stirred at 100 C for 12 h under nitrogen atmosphere. It was quenched with water (150 mL). The resulting solution was extracted with ethyl acetate (5 x 30 mL). The organic layers were combined, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column eluting with dichloromethane/methanol (10 /1). This resulted in 280 mg (41%) of 2-(2-[[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]methyl]-2-methylpropyl)-2,3-dihydro-1H-isoindole-1,3-dione as a yellow oil.

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

Reference:
Patent; PRINCIPIA BIOPHARMA INC.; BABLER, Martin; GERRITSEN, Mary E.; WO2014/22569; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 1074-82-4, 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. 1074-82-4 name is Potassium 1,3-dioxoisoindolin-2-ide, 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.

To a solution of 1,5-dibromopentane (55.9 g, 243 mmol, 32.9 mL) in acetone (250 mL) was added (1,3-dioxoisoindolin-2-yl)potassium (15.0 g, 81.0 mmol) in portions over 30 minutes. The mixture was then stirred at rt for 30 minutes, and then heated to 60 C. and stirred for 15 hrs. On completion, the reaction mixture was filtered and concentrated in vacuo to give a residue. The residue was purified by silica gel chromatography (PE:EA=15:1 to 10:1) to give the title compound (20.0 g, 82% yield) as a white solid. LC-MS (ESI+) m/z 296.0 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Potassium 1,3-dioxoisoindolin-2-ide, and friends who are interested can also refer to it.

Reference:
Patent; Kymera Therapeutics, Inc.; Mainolfi, Nello; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (1443 pag.)US2019/192668; (2019); A1;,
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. 15861-23-1, name is Indoline-5-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 15861-23-1

tert-butyl 3-(5-cyanoindolin-1-yl)pyrrolidine-1-carboxylate To a solution of indoline-5-carbonitrile (110 mg, 0.75 mmol) in 2.5 mL of MeOH was added tert-butyl 3-oxopyrrolidine-1-carboxylate (166 mg, 0.90 mmol) and HOAc (0.11 mL, 1.88 mmol) subsequently. After stirring at room temperature for 10 minutes, NaCNBH3 (57 mg, 0.90 mmol) was added and the mixture was then stirred at ambient temperature for 2 days. The volatiles were removed under vacuum. The residue was diluted with EtOAc, then washed with 1 N NaOH solution and brine, dried over Na2SO4, and evaporated in vacuo to afford the crude title compound for the next step use without further purification.

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 15861-23-1.

Reference:
Patent; Su, Wei-Guo; Deng, Wei; Li, Jinshui; Ji, Jianguo; US2013/210831; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 320734-35-8, 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. 320734-35-8, name is 7-Bromooxindole, This compound has unique chemical properties. The synthetic route is as follows.

To the suspension of VIb (200mg, 0.94 mmol) in water (5 mL) and sodium hydroxide (56mg, 1.41 mmol) was added dimethyl sulphate (178mg, 1.41 mmol) and the mixture was heated at 100 oC for lh. After the consumption of starting material, reaction mixture was cooled to 0 oC, added water and extracted with ethyl acetate. Organic layer was washed with brine, dried over sodium sulphate and evaporated under reduced pressure. So obtained crude was purified by column chromatography by using 10% ethyl acetate in pet-ether to get pure Vic (180 mg).

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

Reference:
Patent; BUGWORKS RESEARCH INDIA PVT LTD; PEER MOHAMED, Shahul Hameed; BHARATHAM, Nagakumar; KATAGIHALLIMATH, Nainesh; SHARMA, Sreevalli; NANDISHAIAH, Radha; (113 pag.)WO2017/199265; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 5428-09-1, name is 2-Allylisoindoline-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. SDS of cas: 5428-09-1

General procedure: An oven-dried, two-necked round-bottom flask containing a stir bar was charged with an aryl bromide 1 (1.0 mmol), Pd(OAc)2 (6.8 mg, 0.03 mmol), K2CO3 (165.9 mg, 1.2 mmol), HQ (15.6 mg, 0.1 mmol), allylamine (1.2 mmol), and DMF (3.0 ml) under nitrogen at room temperature. Following degassing three times, the flask was placed in an oil bath, and the mixture was stirred and heated at the appropriate temperature. After an appropriate reaction time, the flask was removed from the oil bath and cooled to room temperature. Water (20 ml) was added, and the mixture was extracted with CH2Cl2 (3.x.20 ml). The combined organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was purified by flash column chromatography on silica gel using ethyl acetate/hexane as an eluent.

The synthetic route of 2-Allylisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jiang, Zhen; Zhang, Lingjuan; Dong, Chaonan; Ma, Baode; Tang, Weijun; Xu, Lijin; Fan, Qinghua; Xiao, Jianliang; Tetrahedron; vol. 68; 24; (2012); p. 4919 – 4926;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 603-62-3, A common heterocyclic compound, 603-62-3, name is 3-Nitrophthalimide, molecular formula is C8H4N2O4, 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.

3-NITROPHTHALIMIDE (LOOGR) was taken into a hydrogenation kettle and dissolved using 500ML of dimethylformamide. 5% Palladium/carbon (LOGR, 50% wet) was added to the solution and subjected to hydrogenation conditions initially at 20-30C under 20-40psi. After the exothermic nature of the reaction was over, hydrogen pressure was increased to 40-60psi and the temperature to 40-50C. After the hydrogen uptake was over the reaction mixture was filtered while hot and the catalyst removed by filtration. Solvent was removed from the filtrate under reduced pressure at 60-80C. Water (500ml) was added to the residue and the mixture stirred for 30min. The product was isolated by filtration and dried at 60-70C to get 80GR (95%) of yellow crystalline solid of 3- aminophthalimide. Melting point: 263-4C.

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; NATCO PHARMA LIMITED; VENKAIAH CHOWDARY, Nannapaneni; WO2004/43919; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 52351-75-4, A common heterocyclic compound, 52351-75-4, name is 6-Methoxyindoline-2,3-dione, molecular formula is C9H7NO3, 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: To a mixture of 2-hydroxy-1,4-naphthoquinone (1 mmol), isatin (1 mmol) and CH3COOH10 mL, 5-aminotetrazole (1 mmol) was added. The mixture was stirred at reflux for an appropriatetime (Table 2). After completion of the reaction (TLC), the reaction mixture was cooled to roomtemperature and the solvent was evaporated under reduced pressure. Then, the crude product waswashed sequentially with 20 mL saturated NaHCO3 and 20 mL brine, purified by silica gel columnchromatography using petroleum ether: ethyl acetate (v:v = 1:1) as eluent to afford the pure product 4(the copies of all spectral data see Supplementary Materials).

The synthetic route of 52351-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Liqiang; Liu, Yunxia; Li, Yazhen; Molecules; vol. 23; 9; (2018);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 101207-45-8, name is 2-(4-Methylbenzyl)isoindoline-1,3-dione, molecular formula is C16H13NO2, 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. SDS of cas: 101207-45-8

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 (dichloromethane:methanol (with 5% ammonia in water) = 0:1 to 5:1) to give p-tolylmethanamine (160 mg).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 101207-45-8, its application will become more common.

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; (278 pag.)WO2019/115567; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 496-12-8, name is Isoindoline, A new synthetic method of this compound is introduced below., Product Details of 496-12-8

To a solution of isoindoline (335 mg, 2.8 mmol) in DCM (5 ml) is added a 2M solution of trimethylaluminum in toluene (1.4 ml, 2.8mmol) and the resulting solution is allowed to EPO stir at ambient temperature for 30 minutes and is then added to a solution of 2-tert- butoxycarbonylamino-3-(2-chloro-3,4-dimethoxy-phenyl)-propinoic acid methyl ester (520 mg, 1.39 mmol) in DCM (5 ml). The reaction is allowed to stir at ambient temperature for 18 h and carefully quenched with a 10% aqueous solution of citric acid. The resulting biphasic mixture is diluted with DCM (20 ml) and extracted with a saturated solution of Rochelle’s Salt (20 ml). The organic layer is separated, concentrated in vacuo and purified by column chromatography (hexanes-ethyl acetate 15- 60%) resulting in 2-tert-Butoxycarbonylamino -3-(2-chloro-3,4-dimethoxy-phenyl)-l-(l,3-dihydro- isoindol-2-yl)-propan-l-one (300 mg, 47%). 2-tert-Butoxycarbonylamino -3-(2-chloro-3,4- dimethoxy-phenyl)-l-(l,3-dihydro-isoindol-2-yl)-propan-l-one is analyzed by HPLC/Mass Spec.

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; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/38459; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 32692-19-6, 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. 32692-19-6 name is 5-Nitroindoline, 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.

A dry Schlenk tube was charged with Cs2C03 (266 mg, 0.816 mmol). The tube was evacuated for 30 min and then flushed with argon and 9 (150 mg, 0.272 mmol) was added to the tube, followed by Pd2(dba)3 (2.8 mg, 0.003 mmol) and X-Phos (6.5 mg, 0.014 mmol). The mixture was dissolved in dry dioxane (5 mL) and the solution was degassed in an ultrasonic bath for 20 min. Then 5-nitroindoline (67.3 mg, 0.41 mmol) was added and the mixture was stirred for 53 h at 80C. TLC (petrol ether/EtOAc 3:1 ) and mass spectroscopy indicated the formation of partially deacetylated mannoside during the progress of the reaction. Therefore, dry pyridine (2 mL) and dry acetic anhydride (1 mL) were added 50 h after the reaction started to regain fully protected mannoside. Then EtOAc (30 mL) and satd. aq. NaHC03 solution (50 mL) were added to the reaction mixture. The layers were separated and the organic phase was washed with brine (2 x 50 mL). The aqueous layers were extracted with EtOAc (3 x 30 mL). The combined organic layers were dried with Na2S04, filtered and concentrated under reduced pressure. The residue was purified with silica gel chromatography (petrol ether/EtOAc, 10:1 -1 :1 ) to give 10 (128 mg, 80%) as an orange solid.1H NMR (CDCI3): delta 2.02, 2.20 (2s, 12H, 4 OAc), 3.21 (t, J = 8.5 Hz, 2H, CH2), 4.1 1 (m, 4H, CH2, H-6a, H-5), 4.26 (dd, J = 7.3 Hz, 1 H, H-6b), 5.37 (t, J = 9.9 Hz, 1 H, H-4), 5.43 (s, 1 H, H-2), 5.53 (m, 2H, H-1 , H-3), 6.84 (d, J = 8.3 Hz, 1 H, Ar), 6.98 (m, 3H, Ar), 7.30 (t, J = 8.1 Hz, 1 H, Ar), 8.00 (s, 1 H, Ar), 8.05 (d, J = 8.8 Hz, 1 H, Ar).

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

Reference:
Patent; UNIVERSITY OF BASEL; ERNST, Beat; WO2012/164074; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem