Indolines-derivatives

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 169037-23-4 as follows. Computed Properties of C9H4F3NO3

Diethylcyanomethylphosphonate (279 mg, 1.58 mmol) was dissolved in dry THF (6 mL) at 0oC. Sodium hydride (66 mg, 1.15 mmol) was added and, to the resulting suspension, 5-trifluoromethoxyistain (347 mg, 1.50 mmol) was added slowly. Upon completion of the reaction as shown by TLC analysis, water (10 mL), brine (10 mL) and ethyl acetate (10 mL) were added and the aqueous layer extracted with ethyl acetate (3 x 5 mL) and dried with Na2SO4. The solvent was evaporated in vacuo and the resulting solid was purified by column chromatography (PSp:EtOAc 1:0 to 1:1) to yield a yellow product (31%), 1H NMR (400 MHz, CDCl3): d 6.39 (s, 1H), 6.91 (d, J 8.7, 1H), 7.26-7.31 (m, 1H), 7.84 (br s, 1H), 7.94 (d, J 1.9, 1H); 13C NMR (100 MHz, CDCl3): d 99.8, 111.3, 115.3, 118.9, 120.43 (q, J 258), 120.6, 126.9, 141.3, 142.5, 144.8 (q, J 2.1), 165.9; IR (neat, cm-1): 3254, 2228, 1760, 1728, 1624, 1473, 1245, 1124; HRMS: m/z: [M+Na]+ calcd for C11H5N2O2F3Na, 277.0195; found, 277.0188.

According to the analysis of related databases, 169037-23-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Davis, Holly J.; Kavanagh, Madeline E.; Balan, Tudor; Abell, Chris; Coyne, Anthony G.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 15; (2016); p. 3735 – 3740;,
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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 32372-82-0 as follows. Application In Synthesis of Isoindoline hydrochloride

l-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (1.25g, 6.54 mmol, 2.0 eq.) was added to a stirred solution of S6 (1.0 g, 3.27 mmol, 1 eq.), isoindoline hydrochloride (663 mg, 4.26 mmol, 1.3 eq.), 1-hydroxybenzotriazole (1.0 g, 6.54 mmol, 2 eq.) N-,N- diisopropylethylamine (1.72 mL, 9.81 mmol, 3.0 eq.) in dichloromethane (33 mL) at 0 C. The resulting solution was stirred at rt for 14 h before quenching with saturated sodium bicarbonate solution (30 mL). The organic layer was washed with 1 M hydrochloric acid solution (30 mL) and saturated sodium chloride solution (30 mL), dried over sodium sulfate, filtered and concentrated. The residue residue was purified by flash chromatography (Si02, 1 :3hexanes/ethylacetate) to afford S7 (1.22 g, 91.8%) as a colorless oil. 1H MR (400 MHz, CDC13) delta 7.50 (s, 1H), 7.37 – 7.26 (m, 3H), 7.19 – 7.12 (m, 2H), 4.99 (s, 2H), 4.82 (s, 2H), 4.68 (s, 2H), 4.62 (s, 2H), 3.88 (s, 3H), 3.48 (s, 3H). HRMS (ESI+) m/z [M + H+] calcd forC11H14BrO5, 452.1072, found 452.1066.

According to the analysis of related databases, 32372-82-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
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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. 106976-23-2, name is 5-Bromo-6-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Recommanded Product: 106976-23-2

A 30% hydrogen peroxide sol. (2 mL/g) was added to a sol. of isatin derivative in 10 M of sodium hydroxide sol. (10 mL/g) at 70 C. and the reaction mixture was then held at this temperature for 1 h. The mixture was then cooled to 0 C., adjusted to pH 8 with conc. HCl, diluted with EE and then brought to pH 4-5. The organic phase was washed with water, dried (NaSO4) and the solvent removed. (Yield approx. 60%)

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:
Patent; Gruenenthal GmbH; US2009/69320; (2009); A1;,
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Application of 24566-79-8, 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 24566-79-8 as follows.

2-[6-(4-PHENYL-1-PIPERIDINYL)HEXYL]-1H-ISOINDOLE-1,3(2H)-DIONE: To the 500 ml RB-flask was added 4-phenylpiperidine hydrochloride (5 g, 25 mmol), N-(6-bromohexyl)phthalimide (15.5 g, 50 mmol), N,N-diisopropylethylamine (21.8 ml, 125 mmol), tetrabutylammonium iodide (0.2 g), and dioxane (250 ml) at room temperature. The reaction mixture was stirred at 100 C. for 72 h. The solvent was removed in vacuo and the crude product was purified by flash chromatography (98:2=Chloroform: 2N ammonia in methanol) to afford 7.67 g of the desired product (77% yield): 1H NMR (400 MHz, CDCl3) delta 7.78-7.79 (m, 2H), 7.74-7.65 (m, 2H), 7.32-7.14 (m, 5H), 3.69 (t, 2H, J=7.35 Hz), 3.06 (d, 2H, J=11.0 Hz), 2.49 (quintet, 1H, J=7.6 Hz), 2.36 (t, 2H, J=7.6 Hz), 2.02 (t, 2H, J=12.5 Hz), 1.82 (br s, 4H), 1.69 (t, 2H, J=6.3 Hz), 1.54 (br s, 2H), 1.37 (br s, 4H); ESMS m/e: 391.3 (M+H)+; Anal. Calc. for C25H30N2O2+0.2H2O: C, 76.19; H, 7.77; N, 7.11. Found: C, 76.14; H, 7.38; N, 7.13.

According to the analysis of related databases, 24566-79-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Salon, John A.; Laz, Thomas M.; Nagorny, Raisa; Wilson, Amy E.; Craig, Douglas A.; US2004/38855; (2004); A1;,
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Related Products of 104618-32-8, 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 104618-32-8 as follows.

Hydrochloric acid (35%) (3.2 L) was added to a cooled solution of 4-aminobenzamide (2.0 Kg, 14.69 mol) in water (14 L, 7 volumes) at 5-100C. Then p-toluene sulphonic acid (10.1 Kg, 3.44 mol) was added to the reaction mixture and further cooled to -5C to -100C. Sodium nitrite (1.76 Kg, 25.7 mol) was dissolved into water (4 L, 2 volumes) and added to the cooled reaction mixture over a period of 2.5 hours at -5C to -100C and further stirred for 4 hours. Sodium sulphite (5.6 Kg, 44.4 mol) was dissolved into water (16 L, 8 volumes) and added dropwise to the diazonium salt over a period of 3 hours at a temperature of -5C to -100C. After stirring for 2 hours, the temperature of the reaction mixture was allowed to rise to ambient and stirred for 12 hours. The reaction was monitored by TLC. Methanol (16 L, 8 volumes) was added to the yellow suspension and 4-phthalimido- cyclohexanone (4.64 Kg, 19.07 mol) was added portionwise at a temperature of 40-450C. After maintaining the reaction mixture at 40-450C for 30 minutes, the temperature of the reaction mixture was raised to 70-750C and maintained for 8 hours. After completion of the reaction, the mixture was cooled to 25-300C, filtered and washed with water (40 L). The wet cake was mixed with water (40 L) and the pH adjusted to 7-8 using 10% potassium carbonate (aq) solution, and the slurry was filtered and washed with water (40 L). The product was dried under vacuum at 60-650C. The crude product was purified by reflux in dichloromethane (30 L) and dried to afford the title compound (3.70 Kg). Molar yield: 70%HPLC purity: 98.06%

According to the analysis of related databases, 104618-32-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENERICS [UK] LIMITED; MYLAN INDIA PRIVATE LIMITED; GORE, Vinayak Govind; GADKAR, Maheshkumar; TRIPATHI, Anilkumar; MANKAR, Viraj; WO2010/122343; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6326-79-0, name is 6-Bromoisatin, 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 6326-79-0, SDS of cas: 6326-79-0

To a solution of 3a (150 mg, 0.66 mmol) in dry acetone (30 mL) was added Na2CO3 (anh. ) (1.0 g) and dimethylsulfate (0.8 mL) under Ar and the reaction mixture was heated at 60 C for 20 h. Then, the mixture was filtered and the filtrate was carefully evaporated using a high vacuum pump (under 40 C). The solid residue was submitted to flash chromatography with CH2C12 to afford lla (140 mg, 0.58 mmol, 85%) (see Scheme 2 in Fig. 2B).

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Reference:
Patent; THE ROCKEFELLER UNIVERSITY; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; WO2005/41954; (2005); A1;,
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These common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, 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: 7-Chloroisatin

General procedure: In sealed tube, a solution of 3 mL solvent (DMSO or DMF) of hydrazines 1 (0.5mmol), diketones 2 or 4 (0.5mmol), K2CO3 (1mmol), eosin Y (0.025mmol) was sequentially added. The reaction mixture was stirred under incandescent light (0.4 Wcm-2) irradiation at 45 °C for 24 h. Then, the mixture extracted with ethyl acetate (3 × 10 mL), and the organic layer was combined and dried with anhydrous Na2SO4. After removal of the solvent under reduced pressure, the residue was separated by flash column chromatography to afford the pure product 3 or 5 (PE: EA = 20:1).

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

Reference:
Article; Diao, Pinhui; Ge, Yanqin; zhang, Wenpei; Xu, Chen; Zhang, Nannan; Guo, Cheng; Tetrahedron Letters; vol. 59; 8; (2018); p. 767 – 770;,
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Related Products of 132898-96-5,Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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 mixture of cis-N-benzyl-2,5-bis(methoxymethyl)pyrrolidine (18a) (620 mg, 2.49 mmol, 1.00 equiv.) and 10% Pd/C (62 mg, 10% w/w) in MeOH (12 mL) was stirred in an autoclave at ambient temperature under H2 atmosphere (20 atm) for 6 h. After this time, the mixture was filtered through Celite and washed again with MeOH. The solvent was removed under reduced pressure to obtain the corresponding unprotected bis(methoxymethyl)pyrrolidine as a light yellow oil. The solution of obtained free amine cis-2,5-bis(methoxymethyl)pyrrolidine and DIPEA (766 muL, 4.40 mmol, 2.00 equiv.) in CHCl3 (5 mL) was added dropwise to a stirred solution of 5-chlorosulfonyl isatin (1.08 g, 4.40 mmol, 2.00 equiv.) in CHCl3/THF (1:1, 50 mL) at room temperature. The resulting mixture was stirred further for 2 h and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 90% EtOAc in cyclohexane) to yield a yellow solid (723 mg, 1.96 mmol, 89%). M.p. 168 C. 1H NMR (400 MHz, DMSO-d6): delta = 11.46 (br s, 1H, 1-NH), 8.05 (dd, 3JH,H = 8.3 Hz, 4JH,H = 2.0 Hz, 1H, 6-CH), 7.80 (d, 4JH,H = 1.9 Hz, 1H, 4-CH), 7.09 (d, 3JH,H = 8.3 Hz, 1H, 7-CH), 3.73-3.58 (m, 2H, 12-CH, 15-CH), 3.52-3.20 (m, 4H, 16-CH2, 19-CH2), 3.37 (s, 6H, 18-CH3, 21-CH3), 1.78-1.62 (m, 2H, 13-CHa, 14-CHa), 1.57-1.37 (m, 2H, 13-CHb, 14-CHb) ppm. 13C NMR (100 MHz, DMSO-d6): delta = 182.9 (3-CO), 159.4 (2-CO), 153.6 (8-CN), 136.7 (6-CH), 130.8 (5-CSO2), 123.1 (4-CH), 118.1 (9-CCO), 112.7 (7-CH), 74.4 (2C, 16-CH2, 19-CH2), 59.9 (2C, 12-CH, 15-CH), 58.4 (2C, 18-CH3, 21-CH3), 26.9 (2C, 13-CH2, 14-CH2) ppm. HRMS (ESI+, MeOH): m/z = 391.0931 [M + Na]+, 423.1194 [M + Na + MeOH]+; calcd. 391.0934 for C16H20N2O6S + Na, 423.1196 for C16H20N2O6S + Na + MeOH.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Dioxoindoline-5-sulfonyl chloride, its application will become more common.

Reference:
Article; Limpachayaporn, Panupun; Riemann, Burkhard; Kopka, Klaus; Schober, Otmar; Schaefers, Michael; Haufe, Guenter; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 562 – 578;,
Indoline – Wikipedia,
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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. 32692-19-6, name is 5-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H8N2O2

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light yellow solid.

According to the analysis of related databases, 32692-19-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
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Adding a certain compound to certain chemical reactions, such as: 496-12-8, name is Isoindoline, 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 496-12-8, name: Isoindoline

Example 137:; EPO 137To a dichloromethane solution (8 ml.) of phosgene (769 uL, 20% in toluene, 1.45 mmol) at -70C was added triethylamine (234 mg, 2.32 mmol) and isoindoline (138 mg, 1.16 mmol). The mixture was slowly warmed to room temperature and stirred for 1 hour. To the reaction mixture were added 103d (245 mg, 0.980 mmol), triethylamine (147 mg, 1.45 mmol) and 4-(dimethylamino)pyridine (18 mg, 0.15 mmol). The mixture was stirred at room temperature for 72h. It was then diluted with ethyl acetate (30 ml_) and washed with cold 1 M HCI (20 ml_), cold 1 M sodium bicarbonate (20 mL) and brine (20 mL), dried with Na2SO4 and concentrated. After column chromatography (20-40% ethyl acetate in hexane), the title compound was obtained in 57% yield. 1H NMR (CDCI3): delta 7.44 (1H, dd, J=8.6, 5.3Hz), 7.4-7.2 (4H, m), 7.03 (1 H, dd, J=9.8, 2.2Hz), 6.86 (1 H, m), 4.98 (1 H, m), 4.71 (4H, m), 4.25 (2H, m), 3.37 (2H, m), 1.28 (3H, t, J=7Hz). LCMS (APCI): 396.1 (M+H+).

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Reference:
Patent; PFIZER, INC.; WO2006/40646; (2006); A1;,
Indoline – Wikipedia,
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