Author: Jessica.F

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

19727-83-4, name is 6-Nitroindoline, 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. Safety of 6-Nitroindoline

To a stirred solution of 6-nitroindoline (8.0 g, 48.8 mmol) in DCM (50 ml_) was added pyridine (9.9 ml_, 122 mmol), (Boc)2O (10.6g, 48.6 mmol) and catalytic DMAP. EPO The mixture was stirred overnight. Reaction was washed with brine, and the organic layer was dried (Na2SO4), filtered and concentrated. Chromatography (20% EtOAc/hexanes) provided 1-Boc-6-nitroindoline (10 g, 78%).

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; PHARMACOPEIA DRUG DISCOVERY, INC.; WO2007/24944; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 56341-39-0, 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. 56341-39-0 name is 6-Fluoroindolin-2-one, 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.

EXAMPLE 14 A solution of 6-fluorooxindole (227 mg, 1.5 mmol), (prepared according to Synthesis 1993, 51), in THF (3 ml) was added dropwise under nitrogen to sodium hydride (42 mg, 1.75 mmol, pre-washed with hexane). After stirring the resulting mixture for 20 minutes at ambient temperature, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (169 mg, 0.5 mmol), (prepared as described for the starting material in Example 5), was added as a solid, followed by DMF (3 ml). The mixture was then heated at 75 C. for 1 hour, allowed to cool and the solvent removed by evaporation The mixture was partitioned between water and ether. The aqueous layer was separated and adjusted to pH8 with 2M hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed with brine, dried and volatiles removed by evaporation. The residue was triturated with ether and collected by filtration. This solid was dissolved in methylene chloride/methanol, a 5M solution of hydrogen chloride in isopropanol (0.5 ml) was added and the volatiles removed by evaporation. The resulting solid was collected by filtration, washed with ether and dried under vacuum to give 4-(6-fluorooxindol-3-yl)-6-methoxy-7-(3-morpholinopropoxy)quinazoline hydrochloride (198 mg, 81%) as a yellow solid. m.p..195-200 C. 1H NMR Spectrum: (DMSOd6, CF3CO2D) 2.25-2.4(m, 2H); 3.05-3.2(m, 2H); 3.25-3.35(m, 2H); 3.52(d, 2H); 3.72-3.85(m, 2H); 3.9(s, 3H); 4.05(d, 2H); 4.3(t, 2H); 6.8-6.9(m, 2H); 7.32(s, 1H); 7.62-7.7(m, 1H); 7.78(s, 1H); 8.7-8.8(m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Fluoroindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Zeneca Limited; US6265411; (2001); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 22190-33-6,Some common heterocyclic compound, 22190-33-6, name is 5-Bromoindoline, molecular formula is C8H8BrN, 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 stirred solution of 5-bromo-indoline (3.0 g, 15 mmol) in acetonitrile (100 ml), was added DMAP (0.185 g, 1.522 mmol) and di-tert-butyl dicarbonate (3.98 g, 18.3 mmol) and the reaction was stirred at ambient temperature for 16 h. The reaction mixture was concentrated on reduced pressure to obtain a residue which was diluted with diethyl ether and washed with water and brine solution (2×). The combined ether layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product as an off-white solid, which was used in the next step without further purification (3.0 g).

The synthetic route of 22190-33-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US2014/171308; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem