Month: June 2021

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;,
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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;,
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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.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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;,
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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).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Huang, Qi; Qin, Ling; Zard, Samir Z.; Tetrahedron; vol. 74; 40; (2018); p. 5804 – 5817;,
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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;,
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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;,
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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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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. 13220-46-7, name is 4-Methylindolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 13220-46-7

1-(4-Methyl-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-6,7-dihydro-2H-pyrano[3,4-c]pyrrol-4-one 4-Methyl-1,3-dihydro-indol-2-one was condensed with 4-oxo-2,4,6,7-tetrahydro-pyrano[3,4-c]pyrrole-1-carbaldehyde to give the title compound. MS m/z 295.2 [M++1].

The synthetic route of 13220-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tang, Peng Cho; Miller, Todd A.; Li, Xiaoyuan; Zhang, Ruofei; Cui, Jinrong; Huang, Ping; Wei, Chung Chun; US2002/42427; (2002); A1;,
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These common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, 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. name: tert-Butyl 5-aminoindoline-1-carboxylate

A mixture of 2-isopropoxy-4-methylbenzoic acid (2.57 g), tert-butyl 5-AMINO-1-INDOLINECARBOXYLATE (3.41 g), 1- hydroxybenzotriazole hydrate (2.13 g) and 1- [3- (dimethylamino) PROPYL]-3-ETHYLCARBODIIMIDE (2.16 g) in N, N- dimethylformamide (30 ml) was stirred at ambient temperature overnight. The reaction mixture was poured into a mixture of ethyl acetate and water, and the organic layer was washed with brine and dried over magnesium sulfate. The solvent was concentrated in vacuo and the precipitate was collected by filtration to give tert-butyl 5- [ (2-ISOPROPOXY-4- methylbenzoyl) AMINO]-1-INDOLINECARBOXYLATE (4.82 g). 1H-NMR (DMSO-d6): 8 1. 38 (3H, d, J=6.02 Hz), 1.51 (9H, S), 2.36 (3H, s), 3.07 (2H, t, J=8.36 Hz), 3.91 (2H, t, J=8.36 Hz), 4.75-4. 80 (1H, m), 6.89 (1H, d, J=7.98 Hz), 7.04 (1H, s), 7.41 (1H, s), 7.63-7. 69 (2H, m), 7.71 (1H, d, J=7.98 Hz), 10.01 (1H, s)

The synthetic route of tert-Butyl 5-aminoindoline-1-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; DAISO CO., LTD.; WO2004/39795; (2004); A2;,
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Reference of 1336963-95-1, A common heterocyclic compound, 1336963-95-1, name is 6-Bromo-7-fluoroindoline-2,3-dione, molecular formula is C8H3BrFNO2, 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 73-(1 ,4′-bipiperidin-1 ‘-ylmethyl)-7-bromo-8-fluoro-//-(1 -phenylcvclopropyl)-2-r3- (trifluorometh l)phenyll-4-quinolinecarboxamide7-bromo-8-fluoro-3-methyl-2-r3-(trifluoromethyl)phenyll-4-quinolinecarboxylic acidTo a solution of 6-bromo-7-fluoro-1 H-indole-2,3-dione (19 g, 77.8 mmol) in THF (200 mL) was added a solution of KOH (21.8 g, 389 mmol) in water (100 mL) dropwise. After the addition was complete, 1-[3-(trifluoromethyl)phenyl]-1 -propanone (15.73 g, 77.8 mmol) was added and the mixture was heated to reflux for 1.5 h. The THF was removed in vacuo, and the remaining aqueous solution was washed with diethyl ether (3 x 100 mL) and acidified with 1 N HCI to pH 2. The precipitate was collected by filtration to afford 7-bromo-8-fluoro-3- methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (16 g, 68% yield).

The synthetic route of 1336963-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl, A.; CHEUNG, Mui; EIDAM, Hilary, S.; FOX, Ryan, M; HILFKER, Mark, A.; MANAS, Eric, S.; YE, Guosen; WO2011/119704; (2011); A1;,
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