Tag: M.W=200-300

Synthetic Route of 667463-64-1, 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 667463-64-1 as follows.

General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2·NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

According to the analysis of related databases, 667463-64-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
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Some common heterocyclic compound, 5181-35-1, name is 2-(2-Bromoethoxy)isoindoline-1,3-dione, molecular formula is C10H8BrNO3, 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. Product Details of 5181-35-1

To a solution of 2-(2- bromoethoxy)isoindoline- l,3-dione (5 g, 1.85 mmol, product from step 1 of preparation 10) and lH-tetrazole (1.3 g, 1.85 mmol) in dimethylformamide (25 ml) was added cesium carbonate (6.0 g, 1.85 mmol) in a lot wise under stirring at room temperature. The progress of reaction was monitored by performing thin layer chromatography using mixture of acetone and hexane (3.5:6.5) as solvent. After 16 hours the completion of the reaction was confirmed by thin layer chromatography. The reaction mixture was slowly poured into chilled water (200 ml) under stirring. After stirring for 30 minutes, the precipitates formed were filtered and washed with water (50 ml). The solid compound was dried at 40 C for 2 hours under high vacuum to provide 3.2 g of a mixture of 2-[2-(lH-tetrazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)-dione and 2-[2-(2H-tetrazol-2- yl)ethoxy]- lH-isoindole- l,3(2H)-dione in 66% yield. Analysis: Mass: 260 (M+l) for Molecular weight: 259 and for Molecular formula: C11H9N5O3; To a flask containing mixture of 2-[2-(lH-tetrazol- l-yl)ethoxy]- lH-isoindole- l,3(2H)- dione and 2-[2-(2H-tetrazol-2-yl)ethoxy]- lH-isoindole- l,3(2H)-dione (3.0 g, 1.15 mmol, product from step 1) in dichloromethane (30 ml) was added hydrazine hydrate (0.870 ml, 1.73 mmol) at 25-30 C under stirring and continued stirring for 2 hours. The progress of reaction was monitored by thin layer chromatography. After complete conversion, the unwanted solid was filtered out and washed with dichloromethane (12 ml). The filtrate was concentrated at 40 C under high vacuum to obtain 1.5 g of crude mixture of l-[2-(aminooxy)ethyl]- lH-tetrazole and 2-[2-(aminooxy)ethyl]- 2H-tetrazole (about 100 % yield) and used without further purification in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5181-35-1, its application will become more common.

Reference:
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
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Electric Literature of 4702-13-0,Some common heterocyclic compound, 4702-13-0, name is N-Phthaloylglycine, molecular formula is C10H7NO4, 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.

In the (G2a) step, 2 mol of thionylchloride (SOCl2) was added to the compound 1a to produce 2-(1,3-dioxoisoindolin-2-yl)acetic chloride (compound 2a) and the unreacted thionylchloride (SOCl2) was recovered by using an aspirator.

The synthetic route of 4702-13-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERMOLON KOREA CO.,LTD.; WO2009/131324; (2009); A2;,
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Reference of 667463-64-1, A common heterocyclic compound, 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, molecular formula is C9H6BrNO2, 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.

I-5.1 (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 HCl. The organic layer is dried over MgSO4 and concentrated. The crystallized residue is dissolved in DCM, methanol is added and the DCM is removed under vacuum. The crystallized product is filtered with sunction and washed with cold methanol. Yield 63%, m/z 226/228 [M+H]+, rt 1.16 min, LC-MS Method V001-003

The synthetic route of 667463-64-1 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; US2014/275159; (2014); A1;,
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5332-26-3, name is 2-(Bromomethyl)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: 5332-26-3

A solution of n-butyllithium in THF (1.8 ml, 2.5 M, 4.5mmol) was added in to a cooled mixture of HMDS (608 mg, 4.56 mmol) in THF (20 ml) dropwise over 20 min with stirring. The mixture was stirred for 30 min before benzyl 2-(4- ((cyclopropylmethyl)sulfonyl)phenyl)acetate (1.3 g, 3.8 mmol) in THF (5 ml) was added through a syringe dropwise over 10 min. Stirred for another 30 min at -78 followed by the addition of 2-(bromomethyl)isoindoline-1,3-dione (912 mg, 3.8 mmol) in THF (5 ml) was added through a syringe over 10 min. The mixture was stirred at -78 and allowed to reach to room temperature overnight. The mixture was treated with methanol carefully and the solvents were evaporated. The product was purified by flash chromatography to affod the product as a White solid 1.4 g (74% yield). MS (+) ES: 504 (M+H)+.

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

Reference:
Patent; ETERNITY BIOSCIENCE INC.; YAN, Yinfa; ZHANG, Minsheng; LIU, Dong; ZHANG, Fengqi; LIU, Suxing; ZHANG, Rumin; HE, Feng; TAO, Weikang; (211 pag.)WO2019/213470; (2019); A1;,
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Some common heterocyclic compound, 129487-92-9, name is tert-Butyl 5-aminoindoline-1-carboxylate, molecular formula is C13H18N2O2, 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 C13H18N2O2

To a solution of 2-bromo-3-((4-fluorophenyl)ethynyl)pyridine (intermediate 42, 340 mg, 1.23inmol) in anhydrous toluene (15 rnL) was added Pd2(dba)3 (113 mg, 0.123 mmol), XPhos (117 rng,0.246 mmoi) and potassium tert-butoxide (414 mg, 3.69 mrnol) under N2. After 10 mm, tert-butyl5-aminoindoline- I -carboxylate (Intermediate 12, 519 mg, 1.75 mmol) was added and the mixturewas stirred at 20 C for 10 mm, Then, the mixture was heated at 100 C for 3hr, EtOAc and waterwere added. The organic phase was separated and dried (Mg504), filtered and concentrated.Purification IFCC. Si02 0:100 to 30:70, EtOAc/heptane) afforded the title compound (330 mg,62%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 129487-92-9, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BERRY, Cynthia G.B.; CHEN, Gang; JOURDAN, Fabrice Loic; LEBOLD, Terry Patrick; LIN, David Wei; PENA PINON, Miguel Angel; RAVULA, Suchitra; SAVALL, Bradley M.; SWANSON, Devin M.; WU, Dongpei; ZHANG, Wei; AMERIKS, Michael K.; (407 pag.)WO2016/176460; (2016); A1;,
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Synthetic Route of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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 4b (1.00 g, 3.63 mmol) and 7b (1.11 g, 5.45 mmol) in THF (35 mL) was added NH4OAc (2.80 g, 36.3 mmol) in MeOH (35 mL). The reaction mixture was stirred at reflux temperature for 2 h and concentrated. The residue was diluted in CHCl3 and washed with a saturated aqueous solution of Na2CO3. The organic layer was dried over MgSO4 and concentrated. The crude product was purified by column chromatography on silica gel eluting with 0-5% MeOH/CHCl3 to afford 2-{2-[5-(1,3-benzodioxol-5-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione as a yellow amorphous (1.14 g, 69%): 1H NMR (200 MHz, CDCl3, delta): 2.42 (d, J = 0.7 Hz, 3H), 3.22 (t, J = 6.8 Hz, 2H), 4.15 (t, J = 6.8 Hz, 2H), 6.00 (s, 2H), 6.69 (s, 1H), 6.85 (d, J = 8.1 Hz, 1H), 7.09 – 7.35 (m, 2H), 7.69 – 7.87 (m, 4 H); MS (ESI) m/z 459 [M+H]+, 35%, 481 [M+Na]+, 100%, 457 [M-H]-, 100%. To a suspension of 2-{2-[5-(1,3-benzodioxol-5-yl)-4-(4-methyl-1,3-thiazol-2-yl)-1H-imidazol-2-yl]ethyl}-1H-isoindole-1,3(2H)-dione (1.12 g, 2.43 mmol) in EtOH (60 mL) was added hydrazine monohydrate (1.18 mL, 24.3 mmol). The reaction mixture was stirred at reflux temperature for 8 h. The mixture was cooled to room temperature and filtered. The filtrate was concentrated and the crude product was purified by column chromatography on NH-silica gel eluting with 2-7% MeOH/CHCl3 to afford 8b as a pale yellow amorphous (567 mg, 71%): 1H NMR (300 MHz, CDCl3, delta): 2.44 (d, J = 0.9 Hz, 3 H), 2.91 (t, J = 5.9 Hz, 2 H), 3.18 (t, J = 5.9 Hz, 2 H), 6.00 (s, 2 H), 6.70 (d, J = 0.9 Hz, 1 H), 6.86 (d, J = 8.1 Hz, 1 H), 7.24 (dd J = 8.1, 1.7 Hz, 1 H), 7.36 (d, J = 1.7 Hz, 1 H); MS (ESI) m/z 329 [M+H]+, 90%, 351 [M+Na]+, 100%, 327 [M-H]-, 100%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-(1,3-Dioxoisoindolin-2-yl)propanal, its application will become more common.

Reference:
Article; Amada, Hideaki; Sekiguchi, Yoshinori; Ono, Naoya; Matsunaga, Yuko; Koami, Takeshi; Asanuma, Hajime; Shiozawa, Fumiyasu; Endo, Mayumi; Ikeda, Akiko; Aoki, Mari; Fujimoto, Natsuko; Wada, Reiko; Sato, Masakazu; Bioorganic and Medicinal Chemistry Letters; vol. 22; 5; (2012); p. 2024 – 2029;,
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Adding a certain compound to certain chemical reactions, such as: 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, 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 667463-64-1, SDS of cas: 667463-64-1

General procedure: Unless indicated otherwise, a solution of 2-aminobenzamide 1 (0.1 mmol), isatin 2 (0.1 mmol), the catalyst 4e (0.02 mmol), and 5 A molecular sieves (30 mg) in 1,2-dichloroethane (2 mL) was stirred at 70 C for 12 h. Next, the reaction mixture was diluted with acetone, which was then filtered to remove molecular sieves and the solid powder was washed with acetone. The resultant solution was condensed by evaporation under reduced pressure, which was further purified through preparative thin layer chromatography on silica gel to yield pure products 3.

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:
Article; Jiang, Yan; Liu, Yan; Tu, Shu-Jiang; Shi, Feng; Tetrahedron Asymmetry; vol. 24; 20; (2013); p. 1286 – 1296;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6941-75-9, These common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-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.

General procedure: A mixture of 2-(7-methoxynaphthalen-1-yl)ethanamine (compound 3, 101 mg, 0.5 mmol), sodium acetate (82 mg, 1.0 mmol) and cyclic anhydrides 1.0 mmol) in 5mL acetic acid was heated to reflux for 3 h in a round bottomed flask. After the completion of reaction (as evidenced by TLC), the resulting mixture was concentrated under reduced pressure and washed with ethyl acetate (10 mL×3), then the concentrated organic layer was purified by column chromatography on silica gel to obtain pure product.

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chang, Ying; Pi, Weiyi; Ang, Wei; Liu, Yuanyuan; Li, Chunlong; Zheng, Jiajia; Xiong, Li; Yang, Tao; Luo, Youfu; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1672 – 1676;,
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Related Products of 169037-23-4, 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. 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

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′-(o-bromophenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(o-bromophenyl-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5b): Melting point 247-249 C; white solid, 96%; 1H-NMR (CDCl3, 400 MHz): delta/ppm 4.82 (d, J = 13.96 Hz, 1H), 4.58-4.61 (m, 1H), 4.49 (d, J = 10.24 Hz, 1H), 3.79 (d, J = 13.2 Hz, 1H), 3.60 (d, J = 16.82 Hz, 1H), 3.39 (d, J = 5.4 Hz, 1H), 2.94 (d, J = 13.96 Hz, 1H), 2.71-2.77 (m, 1H), 2.41 (d, J = 13.92 Hz, 1H), 6.56-6.61 (m, 2H), 6.98-7.65 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 40.6, 47.4, 52.7, 53.2, 61.3, 67.2, 70.9, 100.8, 110.1, 121.9, 122.4, 122.5, 123.8, 124.5, 126.4, 126.5, 127.2, 128.3, 128.4, 128.5, 128.6, 128.7, 128.9, 129.1, 131.4, 131.6, 131.8, 133.2, 136.3, 138.2, 138.5, 138.6, 144.6, 179.5, 197.1. EI-MS: m/z 869 (M+). Anal. Calcd for C44H34Br2F3N3O3: C, 60.77; H, 3.94; N, 4.83; Found: C, 60.85; H, 3.83; N, 4.72.

The chemical industry reduces the impact on the environment during synthesis 5-(Trifluoromethoxy)indoline-2,3-dione. I believe this compound will play a more active role in future production and life.

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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