Category: indolines-derivatives

These common heterocyclic compound, 222036-66-0, name is 5-Aminoisoindolin-1-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. category: indolines-derivatives

The 5-amino-isoindoline-one (Intermediate 8a, 2.1g, 14.2mmoL), acetone (3.5mL, 47.6mmoL) and sodium cyanide (2.1g, 46.8mmoL) was added to 90percent acetic acid (45mL) in.The addition was complete, stirred at room temperature for 48 hours.To the reaction mixture was added water (50mL) and ethyl acetate (100 mL), separated, the organic phase was washed with water (3 × 50 mL), saturated sodium bicarbonate (50 mL), water (50mL), dried over anhydrous magnesium sulfate , filtered, and the solvent was distilled off under reduced pressure, the residue was purified by flash column chromatography, eluent PE: EA = 1: 1, to give a white solid 2.7g, 88percent yield.

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

Reference:
Patent; Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences,; Duan, WenHu; Wan, huixin; Xia, GuangXin; Mei, deCheng; Lin, Yipeng; Liu, Xuejun; Shen, JingKang; (53 pag.)CN103804358; (2016); B;,
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Synthetic Route of 20780-72-7, These common heterocyclic compound, 20780-72-7, name is 4-Bromoisatin, 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 solution of 4-bromoisatin 30 (100 mg, 0.44 mmol) in degassed THF/water (3:1, 2.5 mL) was added potassium 2-methylphenyltrifluoroborate (114 mg, 0.62 mmol) and K3PO4 (338 mg, 1.59 mmol) followed by Pd(PPh3)2Cl2 (31 mg, 0.04 mmol). The reaction vessel was sealed and heated by microwave irradiation for 4 h at 130 °C. The reaction mixture was cooled to rt, diluted with EtOAc (5 mL) and filtered through Celite®. The organic solution was washed with brine (5 mL) and the resulting aqueous layer was further extracted with EtOAc (2*). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The product was purified via flash column chromatography (eluent 40-60 °C, petrol/EtOAc, 4:1) to afford the title compound (41) as an orange solid (40 mg, 42percent); mp 161-162 °C; numax (solid) 3249, 3017, 2926, 1727, 1603, 1480; deltaH (500 MHz, DMSO-d6) 2.15 (3H, s, CH3), 6.93 (2H, m, C(5)H and C(7)H), 7.14 (1H, d, J = 7.6 Hz, C(6′)H), 7.20-7.26 (1H, m, C(4′)H), 7.30 (1H, d, J = 7.3 Hz, C(3′)H), 7.32-7.37 (1H, m, C(5′)H), 7.56 (1H, app t, J = 7.9 Hz C(6)H), 8.84 (1H, br s, NH); deltaC (125 MHz, DMSO-d6) 19.7, 111.2, 115.7, 125.6, 126.3, 128.6, 128.8, 130.1, 135.7, 136.4, 137.9, 142.8, 149.3, 159.2, 182.0; m/z (ESI-) 236 ([M-H]-, 60percent); HRMS (ESI-) C15H10NO2- ([M-H]-) requires 236.0717; found 236.0719.

Statistics shows that 4-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 20780-72-7.

Reference:
Article; Gianella-Borradori, Matteo; Christou, Ivy; Bataille, Carole J.R.; Cross, Rebecca L.; Wynne, Graham M.; Greaves, David R.; Russell, Angela J.; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 241 – 263;,
Indoline – Wikipedia,
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Electric Literature of 102359-00-2, A common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

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:
Article; Guo, Jing; Zhu, Mingyue; Wu, Tianxiao; Hao, Chenzhou; Wang, Kai; Yan, Zizheng; Huang, Wanxu; Wang, Jian; Zhao, Dongmei; Cheng, Maosheng; Bioorganic and Medicinal Chemistry; vol. 25; 13; (2017); p. 3500 – 3511;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 3485-84-5, name is N-Vinylphthalimide, 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 3485-84-5, HPLC of Formula: C10H7NO2

General procedure: A magnetically stirred solution of the N-vinylphthalimide (173 mg, 1.00 mmol, 1.0equiv) and xanthate (408 mg, 1.50 mmol, 1.5 equiv) in ethyl acetate (2 mL) wasrefluxed for 15 min under a flow of nitrogen. DLP (10 mol %) was then added to therefluxing solution and the olefin was totally consumed in 90 min. The reactionmixture was then cooled down to room temperature, concentrated under reducedpressure and purified by flash chromatography on silica gel (Et2O/petroleum ether =1:2) to give the desired compound 8b as a white solid (419 mg, 0.94 mmol, 94%yield).

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Reference:
Article; Huang, Qi; Qin, Ling; Zard, Samir Z.; Tetrahedron; vol. 74; 40; (2018); p. 5804 – 5817;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, 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 129487-92-9, name: tert-Butyl 5-aminoindoline-1-carboxylate

13c) tert-butyl 5-(2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate A mixture of tert-butyl 5-amino-2,3-dihydro-1H-indole-1-carboxylate (4.10 g), tert-butyl 2-chloropyridin-3-ylcarbamate (4.20 g), Pd2(dba)3 (0.48 g), Xantphos (0.608 g), sodium tert-butoxide (2.52 g) in 2-propanol (64 ml) and toluene (12 mL) was stirred at 90 C. for 40 h, and treated with water and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was suspended in CH3CN and the precipitate was collected by filtration to give tert-butyl 5-(2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl)-2,3-dihydro-1H-indole-1-carboxylate (1.64 g). The filtrate was evaporated and then the residue was chromatographed on silica gel eluting with AcOEt/Hexane=2/1 to afford second crop (1.4 g).MS (ESI+): [M+H]+353.3.

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Reference:
Patent; TANIGUCHI, Takahiko; YOSHIKAWA, Masato; MIURA, Kasei; HASUI, Tomoaki; HONDA, Eiji; IMAMURA, Keisuke; KAMATA, Makoto; KAMISAKI, Haruhi; QUINN, John F.; RAKER, Joseph; CAMARA, Fatoumata; WANG, Yi; US2011/319394; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 99365-40-9, 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. 99365-40-9, name is 6-Bromoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Di-tert-butyl dicarbonate (4.63 g, 21.2 mmol) and sodium hydrogen carbonate (10.7 g, 127 mmol) were added to a stirred solution of 6-bromoindolin-2-one (preparation 1, 3.0 g, 14.2 mmol) in tetrahydrofuran (150 mL) and the mixture was heated to reflux. After 3 hours the mixture was cooled and filtered and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (10:1 hexanes/ethyl acetate) gave the title compound (3.58 g, 81%) as a white solid. LRMS (m/z): 312/314 (M+1)+. 1H-NMR delta (CDCl3): 1.65 (s, 9H), 3.66 (s, 2H), 7.10(d, 1H), 7.27 (d, 1H), 8.03 (s, 1H).

The synthetic route of 6-Bromoindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Laboratorios Almirall, S.A.; EP2108641; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 3783-77-5, 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. 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

(1) Synthesis of N-[3-(N-methoxyimino)butyl]-phthalimide 1.08 g (5.00 mmol) of N-(3-oxobutyl)phthalimide was dissolved in 10 ml of methanol and to the solution was added 0.835 g (10.0 mmol) of O-methylhydroxylamine hydrochloride. To this suspension was added 2 ml of 5N aqueous sodium hydroxide solution, followed by being stirred at room temperature for 16 hours. The reaction mixture was poured into 100 ml of saturated aqueous sodium hydrogencarbonate solution and extracted with chloroform (30 ml*3), and the combined organic layer was dried over magnesium sulfate. Chloroform was distilled off and the residual solids were washed with hexane to give 1.23 g (yield 100%) of the titled compound as white crystals. Melting point 55-64 C., 1 H-NMR spectrum (DMSO-d6, TMS as internal standard); delta=1.86(s, 3H*0.66), 1.91(s, 3H*0.34), 2.5(t, J=6 Hz, 2H*0.66), 2.66(t, J=6 Hz, 2H*0.34), 3.48(s, 3H*0.34), 3.65(s, 3H*0.66), 3.84(t, J=6 Hz, 2H*0.66), 3.87(t, J=6 Hz, 2H*0.034), 7.85(s, 4H)ppm,

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

Reference:
Patent; Mitsubishi Gas Chemical Co., Inc.; US5211738; (1993); A;,
Indoline – Wikipedia,
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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. 337536-15-9, name is 4-Bromoisoindolin-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-Bromoisoindolin-1-one

Step 1. A mixture of 2,4-dichloropyrimidine (116 mg, 0.78 mmol), 4-bromoisoindolin-l-one (150 mg, 0.71 mmol), K2CO3 (196 mg, 1.41 mmol) in DMF (3 mL) was degassed and purged with N2 three times, and then the mixture was stirred at 80C for 14 hours under an inert atmosphere. The resulting mixture was filtered and concentrated under reduced pressure. Purification by prep-TLC (Si02, petroleum ether/ethyl acetate = 3 : 1) provided 9 (80 mg) as a light yellow solid which was used directly in the next step without further purification.

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NUMERATE, INC.; RAIMUNDO, Brian; KOLTUN, Elena S.; GRIFFIN, John; STANGELAND, Eric; (93 pag.)WO2018/49324; (2018); A1;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide, 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 1074-82-4, Product Details of 1074-82-4

Synthesis of the protected ketone monomer was conducted based on a modification of a previously reported protocol (50). Chloroacetone (10 mE, 12.5 mmol) and the potassium salt ofphthalimide (25.5 g, 13.8 mmol) were added to 150 mE of stirred dry acetone. The solution was then heated to 80 C. for 20 hours, after which it was cooled to room temperature and the acetone was removed in a rotary evaporator. The resulting solid was then redissolved in methylene chloride and washed repeatedly with water. The methylene chloride layer was dried over magnesium sulfate, filtered, and removed using a rotary evaporatot The resulting yellow crude solid was washed with diethyl ether several times until the solid became white; this solid was subsequently dried in a vacuum oven to yield purified intermediate A (Scheme 1A). Intermediate A (lOg, 50 mmol) was then added to 180 mE of toluene along with ethylene glycol (5.85 mE, 100 mmol) and dry para-tolenesulfonic acid (934 mg, 5 mmol) and refluxed for 15 hours. The reaction mixture was cooled to room temperature and the ethylene glycol layer was extracted three times with diethyl ether. The toluene and ether fractions were combined and washed three times with 5% (w/v) NaOH followed by deionized water. The organic layer was dried over magnesium sulfate and solvent was removed in a rotary evaporatot The crude was recrystallized from ethanol to yield pure intermediate B (Scheme 1B). Intermediate B was subsequently added to 100 mE of deionized water along with 15 g of NaOH and refluxed for 2 days, with an additional 60 g of NaOH added slowly over the course ofthe reflux. Afierwards, the reaction mixture was cooled to room temperature and extracted three times with 50 mE dichloromethane. The organic layers were then combined and dried over magnesium sulfate, filtered, and concentrated in a rotary evaporator to yield pure product C (Scheme 1C), a slightly yellow oil. Finally, the monomer was prepared by adding product C (21.1 mE, 180 mmol) to a 20% (w/v) NaOH solution (in water) containing 4-hydroxy TEMPO (10 mg, 0.06 mmol). This reaction mixture was brought to 0 C. in an ice bath and methacryloyl chloride (16.5 mE, 174 mmol) was added drop- wise over 2 hours under nitrogen flow. The ice bath was then allowed to warm to room temperature and the reaction left to stir overnight in darkness. Afier this time, stirring was halted and the product was allowed to collect at the top of the reaction flask. The pure monomer product (along with inhibitor) (shown in Scheme 1 D) was then isolated using a separatory funnel. The monomer was stored in the darkness at -20 C. until use. 1H NMR (600 MHz) in DMSO-d5: RNHCH2C(OCH2CH2O)CH3, 1.3 ppm, singlet, 3H;CH2CCH3CONHR?, 2 ppm, singlet, 3H; RNHCH2C(OCH2CH2O)CH3, 3.5 ppm, doublet, 2H; RNHCH2C(OCH2CH2O)CH3, 4 ppm, singlet, 4H; CH2CCH3CONHR?,5.35-5.65 ppm, doublet, 2H; CH2CCH3CONHR?, 6 ppm, sin-glet, 1H.

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Reference:
Patent; McMaster University; Hoare, Todd; Bakaic, Emilia; Smeets, Niels M.B.; Deng, Xudong; (55 pag.)US2016/151535; (2016); 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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., name: 5-Nitroindoline

General procedure: To a stirred solution of aryl halides (1.0 mmol) and indoline/indoline carboxylic acid (1.0 equiv) in dry DMSO (2.0 mL) at rt was added nano CuO (5.0 mol %) followed by Cs2CO3 (2.0 equiv) and heated at 80 C for 8 h. The progress of the reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature and catalyst was filtered, the crude residue was extracted with ethyl acetate (3 × 10 mL). The combined organic layers were extracted with water, saturated brine solution, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (7:3) as eluent to give the corresponding N-substituted indoles in excellent yields. The identity and purity of the product were confirmed by 1H, 13C NMR, and mass spectra.

The synthetic route of 32692-19-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, K. Harsha Vardhan; Satish; Ramesh; Karnakar; Nageswar; Tetrahedron Letters; vol. 53; 24; (2012); p. 3061 – 3065;,
Indoline – Wikipedia,
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