Tag: M.W=200-300

Electric Literature of 667463-64-1, 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. 667463-64-1 name is 6-Bromo-1-methylindoline-2,3-dione, 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.

Step 2: Synthesis of Intermediate 1-12.2 1-12.1 (15.0 g, 63 mmol) and hydrazine hydrate (30 mL, 618 mmol) are heated to 125 C for 72 h. To the cool reaction mixture DCM is added and extracted with water and 1 M HC1. The organic layer is dried over MgSC>4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed in vacuo. The crystallized product is filtered by sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001 003.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter, Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; BINDER, Florian; VINTONYAK, Viktor; WO2014/140075; (2014); A1;,
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Some common heterocyclic compound, 337536-15-9, name is 4-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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. Recommanded Product: 337536-15-9

Carbon monoxide (g, 10 atm) was introduced into a 250-mL pressure tank reactor charged with a solution of 4-bromoisoindolin-l-one (3.0 g, 14.2 mmol), sodium acetate (2.32 g, 28.3 mmol), and Pd(dppf)Cl2 (517 mg, 0.71 mmol) in methanol (150 mL). The resulting solution stirred for 24 h at 100 C and was then cooled to room temperature. The resulting solution was concentrated under vacuum and the residue was diluted with 50 mL of water and extracted with 3×50 mL of ethyl acetate. The combined organic phases were washed with 100 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with ethyl acetate/petroleum ether (1 : 1)) to afford methyl l-oxoisoindoline-4-carboxylate (2.08 g, 77%) as a light brown solid. 1H- NMR (DMSO, 300 MHz) d (ppm): 8.75 (s, 1H), 8.15 (d, J = 7.5Hz, 1H), 7.94 (d, J = 7.5Hz, 1H,), 7.65 (m, 1H ), 4.60 (s, 2H), 3.89 (s, 3H). MS: (ESI, m/z): 192[M +H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 337536-15-9, its application will become more common.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); A1;,
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Reference of 201940-08-1, These common heterocyclic compound, 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-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.

5-Bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (2.97 g, 10 mmol) was azeotropically dried by evaporation from toluene. Tris(dibenzylideneacetone)dipalladium (0) (228 mg, 0.25 mmol), 2-(di-tert-butylphosphino)biphenyl (149 mg, 0.50 mmol) and sodium tert-butoxide (1.34 g, 13.9 mmol) were added and the flask was purged with nitrogen. Toluene (25 mL) then N-methylpiperazine (1.33 mL, 12 mmol) were added and the mixture was heated to 800C for 2 hours. After allowing to cool to r.t. the mixture was diluted with ether, filtered through Celite and concentrated to give a residue that was purified by flash chromatography on silica (2M methanolic ammonia/dichloromethane, 1% to 3% gradient). This afforded the title compound as a brown solid (1.45g, 46%). 1H NMR (MeOH-d4) 7.15 (1H, m), 6.94-6.88 (2H, m), 4.60-4.54 (4H, m), 3.20-3.17 (4H, m), 2.63-2.60 (4H, m), 2.34 (3H, s), 1.52 (9H1 s). MS: [M+H]+ 318.

The synthetic route of 201940-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WO2008/44045; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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 954-81-4, Recommanded Product: N-(5-Bromopentyl)phthalimide

General procedure: A mixture of the intermediates 3a-3e (5 mmol) and corresponding secondary amine 4a-4g (5.5 mmol) was added in CH3CN (20 ml) at the presence of anhydrous K2CO3 (6 mmol). The mixture was heated at 65 C for 6-10 h. The solvent was evaporated in vacuo. The residue was dissolved in CH2Cl2 (25 mL), washed with water (20 mL ¡Á 3), and the combined organic phases were washed with saturated aqueous NaCl (30 mL), dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified on a silica gel chromatography using mixtures of petroleum/acetone as eluent to get the target products TM-1~TM-28.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-(5-Bromopentyl)phthalimide, and friends who are interested can also refer to it.

Reference:
Article; Sang, Zhipei; Wang, Keren; Wang, Huifang; Yu, Lintao; Wang, Huijuan; Ma, Qianwen; Ye, Mengyao; Han, Xue; Liu, Wenmin; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5053 – 5059;,
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Application of 2058-72-2, These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-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.

General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.

The synthetic route of 2058-72-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Radhey M.; Bharadwaj, Kishor Chandra; Tiwari, Dharmendra Kumar; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2975 – 2980;,
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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 104618-31-7 as follows. Application In Synthesis of 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione

(b) 4-(Phthalimido)-cyclohexanone 95 g (0.388 Mol) of 4-(phthalimido)cyclohexanol are dissolved in 600 ml of chloroform and, after the addition of 450 ml of water and 120 ml of sulfuric acid, 90 g (0.3 Mol) of potassium dichromate are added in batches. The internal temperature of the mixture is maintained at between 25 and 30 C. by slight cooling. The mixture is stirred for a further 3 hours, then the chloroform phase is separated of and the mixture extracted twice more with chloroform. After drying and concentration of the extracts 82 g (86.9% of theory) are obtained.

According to the analysis of related databases, 104618-31-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dr. Karl Thomae GmbH; US4731374; (1988); A;,
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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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, A new synthetic method of this compound is introduced below., Quality Control of 5-(Trifluoromethoxy)indoline-2,3-dione

General procedure: A mixture of bisarylidenepiperidin-4-one (1.36 mmoL), isatin (2.72 mmoL) and L-phenylalanine (2.72 mmoL) were heated with stirring in [bmim]Br medium (3 mL) for 1 h at 100 C. After completion of the reaction (TLC), ethyl acetate (2 x 5 mL) was added and the reaction mixture was stirred for 10 min. The organic layer was removed under reduced pressure and the crude product was purified by column chromatography (ethyl acetate:hexane v/v 3:7). 5′-Benzyl-4′-phenyl-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-phenyl-1?-styryl-5-benzylidenespiro[3′.3?]piperidin-4?-one (5a): Melting point 210-212 C; white solid, 94%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 5.00 (d, J = 14.64 Hz, 1H), 4.68-4.72 (m, 1H), 4.34 (d, J = 10.24 Hz, 1H), 3.80 (d, J = 13.92 Hz, 1H), 3.68 (d, J = 16.92 Hz, 1H), 3.47 (d, J = 5.4 Hz, 1H), 3.02 (d, J = 11.72 Hz, 1H), 2.72-2.77 (dd, J = 13.96, 8.08 Hz, 1H), 2.54 (d, J = 13.92 Hz, 1H), 6.56-6.63 (m, 2H), 6.92-7.42 (m, 23H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 39.6, 47.3, 52.8, 53.1, 61.0, 67.3, 70.8, 100.9, 109.7, 121.1, 122.5, 124.1, 124.4, 126.4, 127.3, 128.5, 128.6, 128.7, 128.8, 129.3, 129.6, 130.1, 130.4, 134.5, 136.9, 138.3, 138.4, 138.7, 139.7, 139.8, 144.4, 179.8, 197.1. EI-MS: m/z 711 (M+). Anal. Calcd for C44H36F3N3O3: C, 74.25; H, 5.10; N, 5.90. Found: C, 74.38; H, 5.17; N, 5.81.

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arumugam, Natarajan; Almansour, Abdulrahman I.; Kumar, Raju Suresh; Govindasami, Periyasami; Al-thamili, Dhaifallah M.; Krishnamoorthy, Rajapandian; Periasamy, Vaiyapuri Subbarayan; Alshatwi, Ali A.; Mahalingam; Thangamani, Shankar; Menendez, J. Carlos; Molecules; vol. 23; 5; (2018);,
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Reference of 1035235-27-8, These common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-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.

Step a. A suspension of 3-amino-N-methylisoquinoline-6-carboxamide TFA salt (Intermediate 6, 0.40 g, 1.262 mmol), tert-butyl 4-bromoisoindoline-2-carboxylate (Intermediate 1, 0.15 g, 0.505 mmol), and potassium tert-butoxide (0.28 g, 2.525 mmol) in toluene (10 ml) was degassed with nitrogen for 10 min at rt. BetaIotaNuAlphaRho (0.047 g, 0.050 mmol) and Pd2(dba)3 (0.032 g, 0.050 mmol) were added to the reaction mixture at rt. The reaction mixture was heated at 105C for 2 h. The resulting reaction mixture was cooled to rt, poured into water (20 ml) and extracted with EtOAc (2 x 40 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (4% MeOH in DCM) yielding tert-butyl 4-((6-(methylcarbamoyl)isoquinolin-3-yl)amino)isoindoline-2-carboxylate (0.135 g, 0.322 mmol). LCMS: Method A, 2.278 min, MS: ES+ 419.5.

The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
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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. 104618-32-8, name is 2-(4-Oxocyclohexyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., category: indolines-derivatives

A solution of N-(4-oxocyclohexyl)phthalimide (14, 3.53 g, 15 mmol, 1 eq.) and 4-(methylsulfonyl)phenylhydrazine (2.70 g, 15 mmol, 1 eq.) in glacial acetic acid (110 mL) was heated at reflux for 47 h. The mixture was concentrated in vacuo and the residue was dissolved in CH2Cl2 (200 mL). Afterwards, the organic layer was washed with water (2 * 70 mL) and brine (70 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by fc with a gradient (? = 6 cm, l = 13 cm, v = 60 mL, cyclohexane/CH2Cl2 60:40, 50:50, 30:70, 0:100, CH2Cl2/methanol 100:10, Rf = 0.51 (cyclohexane/ethyl acetate/formic acid 3:7:0.2)). Pale yellow solid, mp 282-284 C, yield 4.50 g (79%). Purity (HPLC): 86.6% (tR = 19.6 min). C21H18N2O4S (394.5 g/mol). Exact mass (APCI): m/z = 395.1072 (calcd. 395.1060 for C21H19N2O4S [M + H+]). 1H NMR (600 MHz, DMSO-D6): delta (ppm) = 2.11 (d, J = 12.3 Hz, 1H, 2-H), 2.64-2.74 (m, 1H, 2-H), 2.92-3.01 (m, 3H, 1-CH2, 4-H), 3.12 (s, 3H, CH3), 3.29-3.33 (m, 1H, 4-H), 4.47-4.54 (m, 1H, 3-H), 7.49 (d, J = 8.6 Hz, 1H, 8-H), 7.56 (dd, J = 8.6/1.4 Hz, 1H, 7-H), 7.84-7.93 (m, 5H, 5-H, 4-Hphth, 5-Hphth, 6-Hphth, 7-Hphth), 11.45 (s, 1H, NH). 13C NMR (151 MHz, DMSO-D6): delta (ppm) = 22.5 (1C, C-1), 24.2 (1C, C-4), 26.2 (1C, C-2), 44.6 (1C, CH3), 47.4 (1C, C-3), 108.3 (1C, C-4a), 111.2 (1C, C-8), 117.3 (1C, C-5), 118.9 (1C, C-7), 123.0 (2C, C-4phth, C-7phth), 126.3 (1C, C-4b), 130.7 (1C, C-6), 131.5 (2C, C-3aphth, C-7aphth), 134.5 (2C, C-5phth, C-6phth), 136.8 (1C, C-9a), 138.5 (1C, C-8a), 167.9 (2C, C=O). FTIR (neat): ? (cm-1) = 3348 (m, N-H), 2939 (w, C-H, aliph), 1697 (s, C=O), 1620 (w, C-C, arom), 1130 (s, SO2).

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 104618-32-8.

Reference:
Article; Heimann, Dominik; Boergel, Frederik; de Vries, Henk; Bachmann, Kim; Rose, Victoria E.; Frehland, Bastian; Schepmann, Dirk; Heitman, Laura H.; Wuensch, Bernhard; European Journal of Medicinal Chemistry; vol. 143; (2018); p. 1436 – 1447;,
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Application of 897957-06-1,Some common heterocyclic compound, 897957-06-1, name is 6-Bromo-1-methylindolin-2-one, molecular formula is C9H8BrNO, 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 3: Synthesis of Intermediate R12To 1-5.2 (32.0 g, 142 mmol) in anhydrous dioxane (400 mL) is added Ri 1 (54.4 g, 241 mmol) andpotassium acetate (41.6 g, 424 mmol). The mixture is purged with Argon, [1, 1?-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) as a complex with dichloromethane (11.2 g, 14 mmol) is added and the mixture is heated to 90 C for 2 h. The reaction mixture is diluted with ethyl acetate and water, the organic layer is washed with water, dried over Mg504 and concentrated. The residue is purified via flash chromatography (cyclohexane / EA = 70:30). Yield72%, m/z 274 [M+H]+, rt 0.67 mi LC-MS Method VOil SOl.

The synthetic route of 897957-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; WO2014/140091; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem