Indolines-derivatives

446292-08-6, name is (S)-2-((2-Oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)isoindoline-1,3-dione, 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. Recommanded Product: 446292-08-6

Reference example 1: Synthesis of (S)-4-{4-[5-(aminomethyl)-2-oxo-l,3-oxazolidin- 3-yl]phenyl}morpholin-3-one sulfate (2: 1) [compound IV-sulfate (2: 1)]26.07 g (61.9 mmol) of (5)-2-({2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-l,3- oxazolidin-5-yl}methyl)-lH-isoindole-l,3(2H)-dione (compound III, obtained from compound II following the process disclosed in the ‘ 823 patent) were suspended in 196 mL of ethanol. 24.0 mL (278.4 mmol) of 40% w/w aqueous methylamine were added to the suspension, and the resulting mixture was heated to 60-65C and maintained at this temperature for about 2.5 hours. The content of unreacted compound III was checked to be below 5% by TLC. At this point, 75.1 g (178.2 mmol) of 20% w/w aqueous sulfuric acid were added over the reaction mixture while keeping the temperature above 60 C. Precipitation was observed during the addition. The resulting suspension was heated to 70-75 C and stirred at this temperature for about 1 hour, then cooled down to 20-25 C and stirred at this temperature for about 1 hour. Subsequently, the suspension was filtered and the collected solid was washed with 26.1 mL of ethanol followed by 26.1 mL of acetone to give 18.4 g of wet (,S)-4-{4-[5-(aminomethyl)-2-oxo-l,3-oxazolidin-3- yl]phenyl}morpholin-3-one sulfate (2: 1) as a white solid. Estimated dry mass: 17.4 g. Yield: 82.7%.

The synthetic route of 446292-08-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICHEM S.A.; MANGION, Bernardino; DURAN LOPEZ, Ernesto; WO2012/35057; (2012); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 496-12-8, These common heterocyclic compound, 496-12-8, name is Isoindoline, 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.

Example 343 (BVT074103); 2-anilino-5-[2-(1,3-dihydro-2H-isoindol-2-yl)-2-oxoethyl]-1, 3-thiazol-4 (5H)-one ;(2-anilino-4-oxo-4, 5-dihydro-1, 3-thiazol-5-yl) acetic acid (25 mg, 1 eq) was dissolved in DCM (1 mL) and 1- [3- (dimethylamino) propyl] -3-ethylcarbodiimide hydrochloride (EDC, 29 mg, 1.5 eq), 1-hydroxybenzotriazole hydrate (HOBt, 20 mg, 1.5 eq), and N- methylmorpholine (NMM, 44 u. L, 4 eq) were added sequentially. After 10 min stirring at room temperature isoindoline (13 pL, 1.1 eq) was added and the reaction mixture was stirred overnight at room temperature H,, O (5 mL) and DCM (5 mL) was added, the organic layer separated on a 1-PS syringe and concentrated. Purified by flashtube DCM- MeOH (14: 1). 17 mg, yield 47%. 1H NMR (400 MHz, CHLOROFORM-D) 8 ppm 2.09-2. 45 (m, 2 H), 4.19-4. 42 (m, 1 H), 4.53-4. 77 (m, 4 H), 7.01-7. 22 (m, 7 H), 7.30-7. 42 (m, 2 H). MS [M+H] + m/z = 352.

Statistics shows that Isoindoline is playing an increasingly important role. we look forward to future research findings about 496-12-8.

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

Synthetic Route of 5332-26-3, These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)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.

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 CHCl3-hexane 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 synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Besterman, Jeffrey M.; Rahil, Jubrail; Vaisburg, Arkadii; US2004/29836; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-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. Formula: C8H4ClNO2

N-4-methylphenylglycine ethyl ester (0.3 mmol) under air atmosphere,A phthalimide compound (0.2 mmol) and cuprous chloride (0.02 mmol) were placed in a dry reaction tube with stirring magnets.Then, an acetonitrile solvent (2 mL) was added to the test tube, and the reaction tube was reacted in an air atmosphere at 60 C for 24 hours.After the reaction is completed, it is cooled to room temperature, and the solvent is distilled off under reduced pressure using a rotary evaporator.The residue is purified by column chromatography to obtain a pure pale yellow solid 3n.The yield was 67%.

The synthetic route of 5-Chloroisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Donghua University Of Science And Technology; Zhu Zhiqiang; Xiao Lijin; Xie Zongbo; Yue Changgao; (12 pag.)CN108623514; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32692-19-6, name is 5-Nitroindoline, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 32692-19-6, COA of Formula: C8H8N2O2

A suspension of 5-nitroindoline (6) (1.0 g, 6.09 mmol) in toluene (20 mL) was treated with 2-chloroacetyl chloride (0.97 mL, 12.18 mmol) and heated at 110 C for 15 min. ;The reaction was cooled to room temperature, treated with sat. ;NaHCO3 solution and extracted into ethyl acetate. ;The combined organic layer was dried (Na2SO4) and concentrated. ;The crude was purified by flash column chromatography (EtOAc:hexanes, 1:9 to 1:1 then 2 M NH3 MeOH: ;CH2Cl2, 1:9) to obtain the title compound (1.08 g, 74%). ;1H NMR (CDCl3) delta 8.30-8.27 (m, 1H), 8.14 (dd, 1H, J = 2.1, 9.0 Hz), 8.06 (s, 1H), 4.30 (t, 2H, J = 8.7 Hz), 4.18 (s, 2H), 3.33 (t, 2H, J = 8.4 Hz); ESI-MS (m/z, %): 241, 243 (MH+).

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Reference:
Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107,14;; ; Article; Annedi, Subhash C.; Maddaford, Shawn P.; Ramnauth, Jailall; Renton, Paul; Rybak, Taras; Silverman, Sarah; Rakhit, Suman; Mladenova, Gabriela; Dove, Peter; Andrews, John S.; Zhang, Dongqin; Porreca, Frank; European Journal of Medicinal Chemistry; vol. 55; (2012); p. 94 – 107;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 41663-84-7, name is 2-Methyl-5-nitroisoindoline-1,3-dione, molecular formula is C9H6N2O4, 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. Computed Properties of C9H6N2O4

Example 4. To a reaction vessel were added 4-nitro-N-methylphthalimide (0.51g, 0. 00248 mol), sodium hydrogen sulfide (0.07g, 0.00125 mol), biphenyl (0.204g, 0.00132 mol), triethylamine (0.2 ml, 0.0014 mol), tetrabutylphosphonium bromide (0.15g, 0.00044 mol) and dry toluene (40 ml). The reaction mixture was allowed to proceed at reflux (approximately 145C) for 18 hours. The reaction mixture was sampled and tested by HPLC which indicated a yield of 4,4′-bis(N-methylphthalimide)sulfide of 10% (0.04g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 41663-84-7, its application will become more common.

Reference:
Patent; GENERAL ELECTRIC COMPANY; EP172298; (1991); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 954-81-4, These common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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.

To a stirred solution of compound 14-k (80 g, 0.27 mol) in DMF (745 mL) was added potassium thioacetate (34 g, 0.29 mol) portion wise over 20 min at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 min. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (1 L) and stirred for 1 h. The resultant precipitate was filtered, washed with water (500 mL) and dried in vacuo to afford 15-k as an off-white solid (75 g, 95%). (1333) 1H NMR (400 MHz, CDC13): delta 7.84 (dd, J= 5.5 Hz, 3.0 Hz, 2H), 7.71 (dd, J= 5.5 Hz, 3.1 Hz, 2H), 3.67 (t, J= 7.3 Hz, 2H), 2.85 (t, J= 7.3 Hz, 2H), 2.30 (s, 3H), 1.73-1.65 (m, 3H), 1.64-1.57 (m, 1H), 1.46-1.37 (m, 2H);LC-MS: 292.2 (M++l).

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; (500 pag.)WO2018/98206; (2018); 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. 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 6-Bromo-7-fluoroindoline-2,3-dione

To a mixture of 6-bromo-7-fluoroindoline-2,3-dione (18.9 g, 77.5 mmol) in 2 N NaOH (350 mL) at 0 oC, H2O2 (30%, 40 mL) was added. The mixture was stirred at room temperature for 16 h. The mixture was quenched with Na2SO3, and the mixture was acidified with conc. HCl to adjust pH to 2. The precipitate was collected by filtration and dried to afford the desired product as a white solid (17 g, 94% yield).

According to the analysis of related databases, 1336963-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARAXES PHARMA LLC; LI, Liansheng; FENG, Jun; LONG, Yun Oliver; LIU, Yuan; WU, Tao; REN, Pingda; LIU, Yi; (335 pag.)WO2016/164675; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, 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. SDS of cas: 2436-29-5

Bromine (0.22 ml, 4.29 mmol) was added dropwise to a solution (30 ml) of 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanal (866 mg, 4.36 mmol) in acetic acid at room temperature. After stirring at room temperature for 2 hours, the reaction solution changed in color from brown to colorless. Thiourea (373 mg, 4.90 mmol) was added to the reaction solution and the resulting mixture was refluxed for 2 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the resulting residue was washed with methanol-diethyl ether and then dried. The solvent was distilled off under reduced pressure to obtain the title compound (616 mg, 55.8%).; LC/MS (M+1, retention time): 260.0, 3.76 min.

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1640369; (2006); 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. 20870-78-4, name is 5-Bromoindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., name: 5-Bromoindolin-2-one

EXAMPLE 58A 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one Under N2, 5-Bromoindolin-2-one (Aldrich, 2.11 g, 10.0 mmol) was coupled with bis(pinacolato)dibon (Frontier Scientific, 3.05 g, 12 mmol) in the presence of KOAc (Aldrich, 1.50 g, 15.0 mmol) under the catalysis of PdCl2(dppf).CH2Cl2 (Aldrich, 163 mg, 0.2 mmol) in anhydrous dioxane (Aldrich, 50 mL) at 85 C. for 15 hours. After the reaction was completed, it was cooled down to ambient temperature and diluted with EtOAc (100 mL). The mixture was then washed with brine (2*10 mL) and concentrated. The residue was purified with chromatography on silica gel (EtOAc/hexanes, v. 1:1, Rf=0.5) to provide the title compound (2.43 g, yield, 93.8%). 1H NMR (300 MHz, CD3OD) delta 1.24 (s, 12H), 3.51 (s, 2H), 6.88 (d, J=8.5 Hz, 1H), 7.52-7.75 (m, 2H) ppm. MS (DCI/NH3): m/z 260 (M+H)+.

According to the analysis of related databases, 20870-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ji, Jianguo; Li, Tao; Lynch, Christopher L.; Gopalakrishnan, Murali; US2008/45539; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem