Month: July 2021

Application of 20870-79-5,Some common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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.

To a suspension of 5-nitroindolin-2-one (5 g, 1 eq.) in EtOH(50 mL), activated carbon (1 g) and FeCl3 (1 g) were added.The mixture was heated to 78 C, and stirred for 10 min.Then 80% aqueous solution of hydrazine hydrate (8 eq.)was added dropwise into the reaction mixture in 5 min, theresulting mixture was stirred at 78 C for 8-10 h, thencooled to room temperature. The mixture was filtered to remove residue of activated carbon; the filtrate was concentratedunder vacuum to afford crude product, which waspurified by recrystallization from EtOH (about 15 mL) togive 5-aminoindolin-2-one as a pale yellow solid (yield91.9%).

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

Reference:
Article; Zhou, Yuanzheng; Ju, Yuan; Yang, Yang; Sang, Zitai; Wang, Zhenling; He, Gu; Yang, Tao; Luo, Youfu; Journal of Antibiotics; vol. 71; 10; (2018); p. 887 – 897;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 35197-64-9, name is 2-Bromo-4-(1,3-dioxoisoindolin-2-yl)butanoic acid, molecular formula is C12H10BrNO4, 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. Product Details of 35197-64-9

Example 373 (BVT056664); 2-{2-[2-(bicyclo [2.2. 1] hept-5-en-2-ylamino)-4-oxo-4, 5-dihydro-1, 3-thiazol-5-yl] ethyl}- I H-isoindole-1, 3 (2H)-dione; 2-bromo-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butanoic acid (0.204 g, 0.654 mmol) and N-bicyclo [2.2. 1] hept-5-en-2-ylthiourea (0.112 g, 0.666 mmol) were dissolved in acetone (15 ml) and heated to reflux for 8h. The reaction mixture was allowed to cool to room temperature. NaHCO3 (sat. solution) was added and extraction with DCM was performed. The organic phase was concentrated in vacuum to give the crude product (0.269 g) of which 10 mg was purified using preparative LC-MS (System C, 20-80% MeCN). 7mg, yield ‘H NMR (270 MHz, CHLOROFORM-D) 1.65-1. 84 (m, 4 H) 2.16-2. 37 (m, 1 H) 2.57-2. 73 (m, 1 H) 2.99-3. 11 (m, 2 H) 3.37 (t, J=4. 58 Hz, 1 H) 3.73-3. 88 (m, 1 H) 3.96-4. 12 (m, 1 H) 4.20 (dd, J=10. 27,3. 59 Hz, 1 H) 6.03-6. 10 (m, 1 H) 6.29 (dd, J=5. 69,2. 97 Hz, 1 H) 7.73- 7.81 (m, 2 H) 7.81-7. 91 (m, 2 H) MS (ESI+) for C2oHi9N303S/ 382 (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 35197-64-9, its application will become more common.

Reference:
Patent; BIOVITRUM AB; WO2005/75471; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 41910-64-9, 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. 41910-64-9, name is 4-Chloroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 2d: 2 ml of toluene, 90 mg of ethyl (1-cyclopropyl-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate and, finally, dropwise, 0.55 ml of a 2M solution of trimethylaluminum in toluene are successively added to a solution of 113 mg of 4-chloroindoline in 4 ml of tetrahydrofuran. The reaction mixture is heated at 90 C. for 4 hours, and then cooled to ambient temperature, and 5 ml of methanol are added. After the addition of 10 g of silica, the reaction mixture is concentrated under reduced pressure. After purification by silica column chromatography (solid deposit), elution being carried out with a mixture of dichloromethane and methanol (100/0 then 98/02 V/V), 39 mg of 2-[2-(4-chloro-2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]-3-cyclopropyl-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of a white solid, the characteristics of which are the following:1H NMR spectrum (400 MHz): 0.83 (m, 2H); 1.07 (m, 2H); 2.69 (m, 1H); 3.18 (t, J=8.6 Hz, 2H); 3.36 (m, 4H); 3.55 (m, 4H); 4.18 (s, 2H); 4.23 (t, J=8.6 Hz, 2H); 5.27 (s, 1H); 7.09 (d, J=8.1 Hz, 1H); 7.21 (t, J=8.1 Hz, 1H); 7.98 (d, J=7.9 Hz, 1H)Mass spectrometry: method ARetention time Tr (min)=0.85;[M+H]+: m/z 415; [M-H]-: m/z 413

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

Reference:
Patent; SANOFI; Brollo, Maurice; Carry, Jean-Christophe; Certal, Victor; Didier, Eric; Doerflinger, Gilles; EL Ahmad, Youssef; Filoche-Romme, Bruno; Halley, Frank; Karlsson, Karl Andreas; Schio, Laurent; Thompson, Fabienne; US2013/274253; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-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. HPLC of Formula: C13H11NO3

To a mixture of DIPEA (5.32 g, 41.17 mmol) and S4 (5.9 g, 25.73 mmol) in DCM (100 mL) was added Tf2O (8.7 g, 30.9 mmol) dropwise at 0 C. for 30 min. The reaction mixture was stirred at 0 C. for 16 hrs. After dilution with DCM, the mixture was washed with aq. NH4Cl solution and aq. NaHCO3solution successively. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated to give crude product, which was purified by column chromatography on silica gel (eluted with petroleum ether: ethyl acetate=4:1) to give the title compound (6.3 g, 67.7% yield) as off-white solid.

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

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 496-12-8, 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. 496-12-8 name is Isoindoline, 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.

Preparation of the title compound was initiated by subjecting the product from step 2 A (0.02 g, 0.03 mmol) to isoindoline (0.01 g, 0.06 mmol) andDBU (0.01 g, 0.06 mmol) in 1 mL DCM at 45 0C for 3 h. Once complete byMS analysis, the reaction was diluted with 10 mL EtOAc and extracted withNaHCtheta3 (2 x 10 mL) and brine (2 x 20 mL). The organic phase was dried over anhydrous Na2SO4, filtered, and then concentrated in vacuo. The residue was purified by silica gel flash chromatography using 70%EtOAc/hexanes affording pyridazinone 4a. (0.01 g, 64 %).MS (ESI) m/z = 755.3 (M+H)+.

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

Reference:
Patent; ENANTA PHARMACEUTICALS, INC.; WO2008/19266; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 19727-83-4, 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 19727-83-4 as follows.

General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.

According to the analysis of related databases, 19727-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 59; 44; (2018); p. 3958 – 3960;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 324-03-8, These common heterocyclic compound, 324-03-8, name is 6-Fluoroindoline-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.

compound 119 6-fluoroindoline-2,3-dione (15.05 g, 91.1mmol), urea (5.47g, 91.1mmol), p-TSA (7.85 g, 45.57 mmol) and methyl acetoacetate (10.6 g, 91.1 mmol) in acetonitrile (500 mL) was refluxed overweekend. The reaction mixture was allowed to cool to room temperature. The precipitate was filtered off. The precipitate was taken up in CH2CI2 (1L) and saturated NaHC03 solution (500mL). The mixture was stirred vigorously during 15 minutes. The precipitate was filtered off and dried in vacuo, resulting in compound 119 as a beige powder (9.25 g). Method A; Rt: 0.61 m/z : 323.1 (M+NH4)+ Exact mass: 305.1; 1H NMR (400 MHz, DMSO-dg) delta ppm 2.24 (s, 3 H), 3.32 (s, 3 H), 6.57 (dd, J=9.4, 2.3 Hz, 1 H), 6.63 – 6.75 (m, 1 H), 7.13 (dd, J=8.0, 5.6 Hz, 1 H), 7.81 (s, 1 H), 8.31 – 11.56 (m, 2 H).

Statistics shows that 6-Fluoroindoline-2,3-dione is playing an increasingly important role. we look forward to future research findings about 324-03-8.

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin Yvonne Paul; ROMBOUTS, Geert; VERSCHUEREN, Wim Gaston; RABOISSON, Pierre Jean-Marie Bernard; WO2013/102655; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 15861-23-1, 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 15861-23-1 as follows.

The compound of Part A (0.1 g, 0.694 mmol) was dissolved in 1,2-dichloroethane (DCE) (2.5 mL) and a solution of the compound of Part B (80 mg, 0.33 mmol) in DCE (1.5 mL) was added. This mixture was stirred for 10-15 min, then treated with sodium triacetoxyborohydride (0.1 g, 0.48 mmol) and stirred overnight at rt under N2. Reaction was quenched by addition of water and 1N NaOH, then extracted 3× with CH2Cl2. Combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 4:1) provided the product (0.105 g, 86%). 1H NMR (CDCl3, 300 MHz) delta 7.94 (d, 1H, J=7.5 Hz), 7.50-(t, 1H, J=7.5 Hz), 7.41 (t, 1H, J=7.5 Hz), 7.34-7.30 (m, 2H), 7.23-7.11 (m, 4H), 5.99 (d, 1H, J=8.4 Hz), 4.08 (dd, 2H, J=24.2, 15.8 Hz), 3.59 (s, 3H), 3.33 (m, 2H), 2.91 (t, 2H, J=8.4 Hz). LRMS m/z 369.0 (M+H)+ (API+). HRMS Calcd. for C24H21N2O2: 369.1603. Found: 369.1580.

According to the analysis of related databases, 15861-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smallheer, Joanne M.; Quan, Mimi L.; Wang, Shuaige; Bisacchi, Gregory S.; US2004/220206; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 181140-34-1, 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. 181140-34-1 name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, 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: Compounds 2-5 were synthesized using a modified procedure originally reported by Roehrig et al.28 To a cooled solution of (R)-(-)-N-(2,3-epoxypropyl)phthalimide 1 (102 mg, 0.50 mmol) in 10 mL of 2-propanol, amine or aminoalcohol (0.6 mmol, 1.2 equiv) in 10 mL of 2-propanol was added at 0 C and stirred for 1 h. It was then refluxed for 8 h. After the completion of the reaction, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silica gel (CHCl3/MeOH 1:20 as eluent) to afford 2-5 as white crystals.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, and friends who are interested can also refer to it.

Reference:
Article; Bozkurt, Selahattin; Durmaz, Mustafa; Naziroglu, Hayriye Nevin; Yilmaz, Mustafa; Sirit, Abdulkadir; Tetrahedron Asymmetry; vol. 22; 5; (2011); p. 541 – 549;,
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. 603-62-3, name is 3-Nitrophthalimide, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H4N2O4

4-Nitro-2-(3-oxobutyl)isoindoline-1,3-done (1) To a solution containing 3-nitrophthalimide (5.00 g; 26 mmol) in ethyl acetate (30 mL), methyl vinyl ketone (2.8 mL; 33 mmol; 1.25 equ.) is added dropwise. After a few minutes of stirring, 760 muL of triton B (Benzyltrimethylammonium hydroxide, 40% in water) are added. The reaction medium is refluxed for 12 hours. After cooling, the solvents are removed under reduced pressure and the solid residue is recrystallized from absolute ethanol in order to obtain the compound 1 as a yellow solid with a yield of 85%. MP: 122 C.; IR (ATR-Ge v cm-1): 1715 (C=O ketone), 1538 (C=C arom), 1373 (N=O2), 1127 (C-C); 1H NMR (CDCl3; 250 MHz) delta8.19-8.07 (m, 2H), 7.93 (dd, J=7.1 Hz, J=8.5 Hz, 1H), 3.98 (t, J=7.3 Hz, 2H), 2.91 (t, J=7.3 Hz, 2H), 2.20 (s, 3H); 13C NMR (CDCl3; 63 MHz) delta205.7 (Cq), 165.6 (Cq), 162.9 (Cq), 145.2 (Cq), 135.6 (CH), 134.2 (Cq), 128.7 (CH), 127.2 (CH), 123.9 (Cq), 41.2 (CH2), 33.8 (CH2), 30.1 (CH3). MS (IS) m/z: 263.0 [M+H]+

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 603-62-3.

Reference:
Patent; UNIVERSITE D’ORLEANS; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S.); US2012/95022; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem