Month: January 2021

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. 19727-83-4, name is 6-Nitroindoline, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H8N2O2

Step A-Preparation of 1-(1-methyl(4-piperidyl))-6-nitroindoline 6-Nitroindoline (5 g) was dissolved in 200 mL of dichloroethane, N-methyl-4-piperidone (5 g) was added to the mixture, followed by 12 g NaBH(OAc)3 and 1 mL of glacial AcOH. The mixture was stirred at RT overnight. Saturated NaHCO3 solution (200 mL) was added to the reaction mixture and stirred for 1 h. The resulting mixture was separated by separation funnel, the organic layer was extracted once with saturated NaHCO3 solution and once with brine. The resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 2:1 EtOAc:MeOH to afford an orange oil. MS: 262 (M+1). Calc’d. for C14H19N3O2-261.32.

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; US6878714; (2005); B2;,
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Electric Literature of 56341-39-0,Some common heterocyclic compound, 56341-39-0, name is 6-Fluoroindolin-2-one, molecular formula is C8H6FNO, 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.

1-(6-Fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-6,7-dihydro-2H-pyrano[3,4-c]pyrrol-4-one 6-Fluoro-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 299.2 [M++1].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Fluoroindolin-2-one, its application will become more common.

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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Related Products of 954-81-4,Some common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, 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: For the synthesis of compounds 6a-d we used commercially available (from Sigma Aldrich) N-(bromoalkyl)isoindoline-1,3-diones. To the solution of N-(bromoethyl)isoindoline-1,3-dione (3.93 mmol) in DMF, sodium azide (11.79 mmol) was added and the contents were heated at 80 C for 6-8 h. After completion, reaction mixture was quenched with ice water and extracted with DCM thrice. The organic extracts were combined, dried over anhydrous sodium suphate, filtered, and concentrated under reduced pressure to give corresponding products as colorless oil and was used without further purification

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-(5-Bromopentyl)phthalimide, its application will become more common.

Reference:
Article; Kushwaha, Khushbu; Kaushik, Nagendra; Lata; Jain, Subhash C.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 7; (2014); p. 1795 – 1801;,
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Application of 1504-06-9, 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. 1504-06-9, name is 3-Methyloxindole, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Oxindole (0.5 mmol), sulfonyl chloride (0.6 mmol), PPh3 (1.0 mmol), n-Bu4NI (0.1 mmol) and dry1,4-dioxane (0.5 mL) were mixed in an oven dried sealed tube. The mixture was stirred at 80 C for12 h. Then, the solvent was evaporated under reduced pressure and the residue was purified by silicagel column chromatography (PE:EA = 5:1 or PE:EA = 3:1) to afford the pure product.

The chemical industry reduces the impact on the environment during synthesis 3-Methyloxindole. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhao, Xia; Wei, Aoqi; Lu, Xiaoyu; Lu, Kui; Molecules; vol. 22; 8; (2017);,
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Related Products of 20870-78-4, The chemical industry reduces the impact on the environment during synthesis 20870-78-4, name is 5-Bromoindolin-2-one, I believe this compound will play a more active role in future production and life.

Reference Example 27 Production of (Z)-5-((5-bromo-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide To the solution of 5-bromoindolin-2-one (262 mg, 1.24 mmol) in EtOH (5 ml) was added N-(2-(diethylamino)ethyl)-5-formyl-2,4-dimethyl-1H-pyrrole-3-carboxamide (298 mg, 1.12 mmol) and piperidine (112 muL, 1.13 mmol). The mixture was stirred at 80 C. for 1 hour. After cooled down to room temperature, the reaction mixture was concentrated, filtrated, and washed with EtOH to give (Z)-5-((5-bromo-2-oxoindolin-3-ylidene)methyl)-N-(2-(diethylamino)ethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide (368 mg) as orange solid. MS m/z 459.4/461.4 (M+H)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Bromoindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Tsuboi, Katsunori; Takanashi, Yosuke; Tojo, Shingo; Kodama, Tomohiro; Kubota, Katsumi; Kanai, Toshio; US2014/275076; (2014); A1;,
Indoline – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 3416-57-7, name is 2-(2-Oxopropyl)isoindoline-1,3-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 3416-57-7, Recommanded Product: 3416-57-7

5.3. Example 3; Cyanoacetamide (62 g, 1.5 eq) and powdered lithium hydroxide (18 g, 1.5 eq) were mixed in 500 ml DMF and it was stirred at room temperature for 30 min. To the mixture was added a solution of phthalimidoacetone (100 g, 0.49 mol, purchased from TCI America, Portland, Oreg., USA, or prepared according to Lei, et al, J. Am. Chem. Soc. 2004, 126, 1626) in DMF (200 ml) over 1 h at room temperature. Additional DMF (25 ml) was used as a rinse. After stirring at room temperature for 5 min, HPLC/MS showed formation of the adol compound (MS: MH+=222.1, MNa+=244.0). Methanol (50 ml) was added followed by 25% sodium methoxide solution (160 g, 1.5 eq) and methanol rinse (50 ml). This mixture was heated at 60-65 C. for 2 h to form 2-amino-4-methyl-1H-pyrrole-3-carboxamide. To this reaction mixture was added ethyl formate (100 ml, 2.5 eq) at 40-60 C. After stirring for 15 min, more methanol (50 ml) was added followed by simultaneous addition of ethyl formate (100 ml, 2.5 eq) and 25% sodium methoxide solution (266 g, 2.5 eq) over 30 min. Additional methanol (50 ml) was added as rinse. The resulting mixture was heated at 60 C. for 5 h. More 25% sodium methoxide solution (113 ml, 1 eq) was added, and heating continued for 1 h more to convert all of the pyrrole N-formyl intermediate (MS: MH+=151.1). Water (400 ml) was added and mixture was heated at 60 C. for 30 min. Solution assay indicated the final product was formed in 69% yield. The hydrolyzed reaction mixture was concentrated under vacuum and diluted with water (1000 ml). The pH was adjusted to about 7.6 with 6 N HCl at 60-65 C. The resulting slurry was heated at 60-65 C. for 15 min and cooled slowly to 10 C. The solids were filtered, washed with water, and dried at 50-60 C. under vacuum. The final product was obtained as a light purple solid (39.5 g, 54% yield, purity: 99.8% by HPLC area).; 5.5. Examples 5-13; Similar to Examples 3 and 4,5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ol was prepared using the following solvent/base combinations for the preparation of the 2-amino-4-methyl-1H-pyrrole-3-carboxamide intermediate:

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; Bednarz, Mark S.; Kanamarlapudi, Ramanaiah C.; Wu, Wenxue; US2008/97098; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 169037-23-4,Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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 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′-(m-methoxyphenyl)-5-(trifluoromethoxy)spiro[3,2′]oxindolopyrrolidino-4′-(m-methoxyphenyl)-1?-styryl-5-benzylidene-spiro[3′.3?]piperidin-4?-one (5k): Melting point 285-287 C; white solid, 94%;1H-NMR (CDCl3, 400 MHz): delta/ppm 4.99 (d, J = 14.64 Hz, 1H), 4.68-4.71 (m, 1H), 4.39 (d, J = 10.24 Hz, 1H), 3.85 (d, J = 13.92 Hz, 1H), 3.80 (s, 3H), 3.78 (s, 3H), 3.70 (d, J = 16.92 Hz, 1H), 3.53 (d, J = 15.4 Hz, 1H), 3.03 (d, J = 11.72 Hz, 1H), 2.79-2.86 (dd, J = 13.96, 8.08 Hz, 1H), 2.72 (d, J = 13.92 Hz, 1H), 6.60-6.67 (m, 2H), 7.13-7.63 (m, 21H, Ar); 13C-NMR (CDCl3, 100 MHz): delta/ppm 39.6, 47.3, 52.6, 53.3, 55.4, 55.5, 61.2, 67.4, 70.9, 100.8, 109.7, 114.2, 114.3, 121.5, 122.3, 122.4, 124.5, 124.6, 124.8, 126.5, 127.4, 128.6, 128.8, 128.5, 128.7, 129.4, 129.9, 130.2, 130.6, 134.6, 136.8, 138.4, 138.4, 138.7, 139.8, 139.7, 144.3, 179.4, 197.5. EI-MS: m/z 771 (M+). Anal. Calcd for C46H40F3N3O5: C, 71.58; H, 5.22; N, 5.44. Found: C, 71.66; H, 5.32; N, 5.55.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-(Trifluoromethoxy)indoline-2,3-dione, its application will become more common.

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);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 7147-90-2,Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, 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.

4-Chlorophthalimide (273 mg) is dissolved in a minimum of boiling ethanol (ca. 2.5 ml). 37% formaldehyde solution (0.15 ml) is added to the still hot solution followed by N-(4-chlorophenyl)glycine (279 mg). Reflux is continued for 3 h. The yellow solution is kept in the refrigerator overnight. The yellow precipitate is collected by suction filtration, washed with ethanol, and dried in vacuo. The crude is recrystallised from ethanol to provide N-[(5-chloro-1,3-dioxo-2-isondolinyl)methyl]-N-(4-chlorophenyl)glycine (135 mg) as light yellow crystals. 1H-NMR (500 MHz, DMSO-d6): delta (ppm)=4.26 (s, 2H), 5.24 (s, 2H), 6.97 (d, J=9.1 Hz, 2H), 7.22 (d, J=9.1 Hz, 2H), 7.90 (d, J=1.2 Hz, 2H), 7.97 (t, J=1.2 Hz, 1H), 12.71 (br s, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=51.77 (CH2), 54.72 (CH2), 114.39 (2CH), 121.70 (C), 123.35 (CH), 124.99 (CH), 128.39 (2CH), 129.97 (C), 133.41 (C), 134.38 (CH), 139.41 (C), 145.34 (C), 167.01 (CO), 167.35 (CO), 171.48 (CO).MS (+ESI): m/z=379 (M+H).

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
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Indoline | C8H9N – PubChem

Some common heterocyclic compound, 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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 70478-63-6

Step a. To a solution of 4-bromoisoindoline-l,3-dione (CAS Number 70478-63-6, 15.00 g, 66.4 mmol) in DCM (150 ml) was dropwise added methyl magnesium bromide (1 M in THF) (199 ml, 199 mmol) at 0¡ãC under N2 atmosphere. The reaction mixture was stirred at rt for 2 h. The reaction mixture was combined with three other batches prepared on the same scale by an identical method. The resulting reaction mixture was poured in to NH4C1 solution (500 ml) and extracted with the DCM (3 x 1 L). The combined organic phases was dried over Na2S04, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (30-32 percent EtOAc in hexane) yielding a mixture of 7-bromo-3-hydroxy-3-methylisoindolin-1-one and 4-bromo-3-hydroxy- 3-methylisoindolin-1-one (37.00 g, 153.6 mmol). LCMS: Method A, 1.435 min, MS: ES+ 242.33, 244.33.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 70478-63-6, its application will become more common.

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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Reference of 181140-34-1, These common heterocyclic compound, 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, 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.

A mixture of 243.9 g (1.20 mol) of S – (+) – N- (2,3-ethoxypropyl) phthalimide (SM1), 121.8 g (800.30 mmol)2- (4-aminophenylamino) ethanol was added to 3L three-necked flask in turn, then 2.0L of anhydrous ethanol was added, and the temperature was raised at 75-85C for 24 h. With tap water to 40 ~ 45 , filter, washed with ethanol, filter cake, white solid. And dried at 50 to 60 C under reduced pressure for 5 hours. To give 256.0 g of compound I in a yield of 90.0%.

Statistics shows that (R)-(-)-N-(2,3-Epoxypropyl)phthalimide is playing an increasingly important role. we look forward to future research findings about 181140-34-1.

Reference:
Patent; Chongqing Zhien Pharmaceutical Co., Ltd.; Deng Xianglin; Li Daming; Huang Chaoming; Huang Minghui; Feng Yongmei; Wang Fei; Liao Xingting; (29 pag.)CN106432218; (2017); A;,
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