Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 13220-46-7, name is 4-Methylindolin-2-one, 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 13220-46-7, Product Details of 13220-46-7

4-Methyl-2-oxindole (5 g) in 40 mL of acetonitrile was treated with 7.26 g of N-bromosuccinimide and stirred at room temperature for 4 hours. Thin layer chromatography (ethyl acetate:hexane 1:2, silica gel) showed a mixture of 5-bromo (Rf 0.3) and 5,7-dibromo (Rf 0.5) products. Another 7,26 g of N-bromosuccinimide was added and the mixture stirred for 4 additional hours. The solid was collected by vacuum filtration, washed with 20 mL of acetonitrile and dried to give a 1:1 mixture of mono and dibromo compounds. The filtrate was concentrated and chromatographed on silica gel (ethyl acetate:hexane (1:2)) to give 1.67 g of 5-bromo-4-methyl-2-oxindole as a beige solid. The remaining 1:1 mixture of solids was recrystallized twice from glacial acetic acid to give 3.2 g of 5,7-dibromo-4-methyl-2-oxindole as a light orange solid. The filtrates from this material were chromatographed as above to give 0.6 g of 5-bromo-4-methyl-2-oxindole and 0.5 g of 5,7-dibromo-4-methyl-2-oxindole

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; Sugen, Inc.; US6878733; (2005); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 102359-00-2

[Example 6] (3E)-3-((5-((E)-(1-acetyl-2-oxoindolin-3-ylidene)methyl)furan-2-yl)methylene)-2-oxoindoline-5-carboxylic acid (5) 5-carboxyindolin-2-one (1 equivalent), 3-((5-formylfuran-2-yl)methylene)-N-acetyl-2-oxoindoline (1.2 equivalents) and piperidine (0.2 equivalent) were dissolved in ethanol such that 1 mL of ethanol was used per 1 mumol of the total amount of the compounds, and the resulting mixture was stirred at room temperature for 2 hours. After completion of the reaction, the resulting precipitate was collected by filtration, washed with cooled ethanol several times and dried, whereby a target compound was obtained. 1H-NMR (d6-DMSO, 400 Mz): 9.41 (s, 1H), 9.39 (s, 1H), 8.42 (d, J= 3.91 Hz, 1H), 8.32 (d, J= 3.91 Hz, 1H), 8.07 (s, 1H), 7.98 (s, 1H), 7.92 (d, J= 8.05 Hz, 1H), 7.82 (d, J= 8.05 Hz, 1H), 7.60 (s, 1H), 7.55 (dd, J= 8.21 Hz, 1.72 Hz, 1H), 7.36 (d, J= 7.22 Hz, 1H), 7.26 (d, J= 7.22 Hz, 1H), 6.87 (m, 1H), 2.66 (s, 3H), MS m/z: 440(M)+

The synthetic route of 102359-00-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Theravalues Corporation; EP2130829; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 114041-16-6, These common heterocyclic compound, 114041-16-6, name is 5,6-Dimethoxyisoindoline, 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.

Compound 416 :In a 10 mL microwave tube, compound 415 (100 mg, 0.23 mmol) was combined with 5,6-dimethoxyisoindoline (42 mg, 0.23 mmol), triethylamine (69 mg, 0.69 mmol) and acetonitrile (2 mL). The solution was irradiated for 30 minutes at 100 C, then diluted with EtOAc and filtered over a short plug of silica gel, rinsing with EtOAc, to afford the intermediate compound 416. HPLC- MS tR = 1.71 min (UV254 nm); Mass calculated for C24H24N8O3: 572.3; Observed m/z: 573.3 (M+H).

The synthetic route of 114041-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WO2009/14637; (2009); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 3484-35-3,Some common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-one, molecular formula is C9H9NO, 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: To a solution of 3-substituted-5-benzylidene-2-thioxo-4-thiazolidinone (1-19) (0.003 mol) in 1,4-dioxane (15 mL) was added HC(OEt)3(2 mL) and BF3Et2O (2 mL). The reaction mixture washeated to 80 C and stirring was continued at the same temperature for 4 h. Theresulting 2-ethylthio-3-substituted-5-benzylidene- 4-thiazolium fluoroborate (Ic, IIc) was precipitated, filteredoff, and dried without any additional purification, as starting material forthe following reactions. To a mixture of thiazolium fluoroborate (Ic, IIc) (0.003 mol) and correspondingindolin-2-one (0.003 mol) in acetonitrile (15 mL) was added triethylamine (0.91g, 0.009 mol) dropwise at 25 C, and the mixture was stirred for 4 h at thesame temperature. The orange precipitate was collected and washed with ethylacetate (8 mL). The crude product thus obtained was recrystallized frommethanol or acetone to give compound (1-19).

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

Reference:
Article; Wang, Feng; Liu, Zijian; Wang, Jian; Tao, Jun; Gong, Ping; Bao, Xue; Zhao, Yanfang; Wang, Yulin; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 126 – 132;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 7477-63-6, name is 7-Chloroisatin, 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 7477-63-6, HPLC of Formula: C8H4ClNO2

General procedure: To a solution of isatin derivative (0.68mmol, 1.0eq) in DMF (4mL) was added K2CO3 (0.68mmol, 1.0eq) at room temperature, the mixture was stirred for about 30min, and then the propargyl bromide (0.75mmol, 1.1eq) was added dropwise. The mixture was stirred for 6-10hat room temperature depending on the isatin derivative used. Upon completion, EtOAc and H2O were added. The aqueous layer was extracted with EtOAc; the combined organic layers were washed with H2O for several times to remove the DMF, and then washed with brine, dried over MgSO4 and evaporated to give the products. Brown solid, yield: 88%, m. p.: 151.7-152.4C, Rf=0.47(petroleum ether/ethyl acetate=2/1). 1H NMR (400MHz, CDCl3) delta 7.67-7.54 (m, 2H), 7.22-7.09 (m, 1H), 4.93 (d, J=2.5Hz, 2H), 2.33 (t, J=2.5Hz, 1H).13C NMR (100MHz, CDCl3) delta 181.76, 157.88, 145.28, 140.55, 125.21, 124.18, 120.60, 117.95, 77.50, 72.94, 31.84

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Chloroisatin, and friends who are interested can also refer to it.

Reference:
Article; Yu, Bin; Qi, Ping-Ping; Shi, Xiao-Jing; Huang, Ruilei; Guo, Hao; Zheng, Yi-Chao; Yu, De-Quan; Liu, Hong-Min; European Journal of Medicinal Chemistry; vol. 117; (2016); p. 241 – 255;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 3676-85-5, These common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-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.

Example 50 1-(7-(3,4-Dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(1,3-dioxoisoindolin-5-yl)piperidine-3-carboxamide Procedure: To a solution of 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidine-3-carboxylic acid (50 mg, 0.12 mmol) and 5-aminoisoindoline-1,3-dione (19 mg, 0.12 mmol) in pyridine (8 mL) was added POCl3 (0.3 mL, 3.23 mmol) at 0 C., the reaction mixture was stirred at room temperature for 4 hours, a sat.NaHCO3 solution was added slowly, the solvent was removed in vacuo, water (5 mL) and methanol (2 mL) were added. The precipitate was collected by filtration and washed with water (5 mL) and methanol (5 mL) to afford 1-(7-(3,4-dimethoxyphenylamino)thiazolo[5,4-d]pyrimidin-5-yl)-N-(1,3-dioxoisoindolin-5-yl)piperidine-3-carboxamide (27 mg, 40.0%) as an orange solid. 1H NMR (300 MHz, DMSO): delta 11.20 (s, 1H), 10.59 (s, 1H), 9.64 (s, 1H), 8.83 (s, 1H), 8.13 (s, 1H), 7.86-7.73 (m, 2H), 7.63 (s, 1H), 7.38-7.29 (m, 1H), 6.78 (s, 1H), 4.77 (d, 1H, J=12.0 Hz), 4.62 (d, 1H, J=12.3 Hz), 3.66 (s, 3H), 3.61 (s, 3H), 3.16-2.94 (m, 2H), 2.60-2.55 (m, 1H), 2.04-2.01 (m, 1H), 1.76-1.72 (m, 2H), 1.52-1.41 (m, 1H). LC-MS: 560 [M+H]+, tR=1.49 min. HPLC: 99.49% at 214 nm, 99.47% at 254 nm, tR=5.33 min.

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hermann, Johannes Cornelius; Lowrie, JR., Lee Edwin; Lucas, Matthew C.; Luk, Kin-Chun Thomas; Padilla, Fernando; Wanner, Jutta; Xie, Wenwei; Zhang, Xiaohu; US2012/252777; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 65826-95-1, 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. 65826-95-1, name is 5-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Preparation 7; 1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-1H-indol-6-ylamineThe synthetic procedure used in this preparation is outlined in Scheme G. Step 1 5-Methyl-6-nitroindolineTo a solution of 2.5 g 5-methylindoline in 20 ml. of concentrated. Sulfuric acid at 0 C. was added in portions 1.7 g of potassium nitrate, keeping the temperature below 5 C. After the addition was complete, the mixture was stirred at 5 C. for ten minutes and then poured onto ice. The aqueous solution was made alkykline with 10% sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine and then dried over sodium sulfate, filtered and concentrated in vacuo. The residue crystallized on standing to give 2.75 g of 5-methyl-6-nitroindoline as a yellow solid.

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-Methylindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Berger, Jacob; Caroon, Joan Marie; Krauss, Nancy Elisabeth; Walker, Keith Adrian Murray; Zhao, Shu-Hai; Lopez-Tapia, Francisco Javier; US2010/160373; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 19155-24-9, These common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-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.

To a mixture of 3,3-dimethyloxindole 41 (100 mg,0.62 mmol, 1.00 equiv) and Cs2CO3 (403 mg, 1.24 mmol, 2.00 equiv) in THF (3.10mL) was added m-nitrobenzyl bromide (335 mg, 1.55 mmol, 2.50 equiv). Thereaction mixture was stirred overnight. Then, the reaction mixture was extracted withEtOAc (3 x 4 mL) and washed with brine. The combined organic phases were driedover MgSO4 and concentrated in vacuo. The residue was purified by columnchromatography (1:4 ? 1:2 EtOAc:hexanes) on silica gel to afford N?3-nitrobenzyl-3,3-dimethyloxindole 3b (170 mg, 92percent yield).Rf = 0.35 (1:2 EtOAc:hexanes); 1H NMR (500 MHz, CDCl3) delta 8.16 ? 8.11 (m, 2H),7.60 (ddt, J = 7.7, 1.8, 0.9 Hz, 1H), 7.53 ? 7.48 (m, 1H), 7.26 ? 7.24 (m, 1H), 7.17 (td,J = 7.7, 1.3 Hz, 1H), 7.07 (td, J = 7.5, 1.0 Hz, 1H), 5.01 (s, 2H), 1.46 (s, 6H); 13CNMR (126 MHz, CDCl3) delta 181.7, 148.6, 141.1, 138.5, 135.9, 133.3, 130.1, 127.9,123.2, 122.9, 122.8, 122.2, 108.7, 77.2, 44.4, 43.0, 24.7; IR (Neat Film NaCl) 2969,1652, 1538, 1348, 1011, 933, 761; HRMS (MM: ESI-APCI+) m/z calc?d forC17H17N2O3 [M+H]+ : 297.1234; found: 297.1241.

The synthetic route of 19155-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Seo-Jung; Fernando De Melo, Gabriel; Stoltz, Brian M.; Tetrahedron Letters; vol. 55; 47; (2014); p. 6467 – 6469;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 13220-46-7, name is 4-Methylindolin-2-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

5-(2-Hydroxy-3-morpholin-4-yl-propyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 53f (30 mg, 0.09 mmol) and 4-methyl-1,3-dihydro-indol-2-one (12 mg, 0.08 mmol) were dissolved in 156mul of ethanol, and added with 4.4mul of piperidine to the solution at room temperature. Upon completion of the addition, the reaction mixture was stirred at 45C for 16 hours. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was naturally cooled down to room temperature, and filtered. The filter cake was washed with anhydrous ethanol (1 ml¡Á2) and dried to obtain the title compound (R,Z)-5-(2-hydroxy-3-morpholinopropyl)-3-methyl-2-((4-methyl-2-oxoindolin-3-ylidene)methyl)-5,6,7,8-tetrahydropyrrolo[3,2-c]azepin-4(1H)-one76(12 mg, yield 30%) as a orange solid. MS m/z (ESI): 465.2(M+1) 1NMR(400 MHz, DMSO-d6) delta13.71(s, 1H, pyrrole-NH),10.92 (s, 1H, indole-NH), 7.57(s, 1H, -CH=C), 7.07?6.77(m, 3H, -ArH) , 4.72(d, 1H, -OH),3.90(m, 1H, -CHOH), 3.78(dd, 1H, seven membered ring outer amide-NCH2), 3.58(t, 4H, morpholin intra 2¡Á-CH2O), 3.40(m, 2H, seven membered ring -NCH2), 3.17(dd, 1H, seven membered ring outer amide-NCH2), 2.94(t, 2H, pyrrole-CH2), 2.59(s, 3H, benzylmethyl), 2.44(m, 4H, morpholin intra 2¡ÁCH2N), 2.39(s, 3H, pyrrole -CH3), 2.29(m, 2H, morpholin outer-NCH2), 2.08(m, 2H, seven membered ring CH2-CH2-CH2).

The synthetic route of 4-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hengrui Pharmaceutical Co. Ltd.; EP2157093; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 59-48-3, 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. 59-48-3, name is Indolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

5-Nitro-2-oxindole 2-Oxindole (6.5 g) was dissolved in 25 ML concentrated sulfuric acid and the mixture maintained at -10 to -15 C. while 2.1 ML of fuming nitric acid was added dropwise.. After the addition of the nitric acid the reaction mixture was stirred at 0 C. for 0.5 hr and poured into ice-water.. The precipitate was collected by filtration, washed with water and crystallized from 50% acetic acid.. The crystalline product was then filtered, washed with water and dried under vacuum to give 6.3 g (70%) of 5-nitro-2-oxindole.

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, Indolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem