Category: indolines-derivatives

65826-95-1, name is 5-Methylindoline, 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. Application In Synthesis of 5-Methylindoline

General procedure: In a 2-neck RBF, 1 (20 mg, 0.0005 mmol) and TMNO (45 mg, 0.6 mmol) were suspended in toluene (4 mL) and to this solution indoline (60 mg, 0.5 mmol) was added. The reaction mixture was then heated to 100 oC for 20 h and it was filtered and solvent evaporated. The crude product obtained was purified by column chromatography using hexane/ethylacetate (7:1) as eluent to give pure indole (47 mg, 79%). A similar procedure was used for the other indolines and N-heterocycles.

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kumaran, Elumalai; Leong, Weng Kee; Tetrahedron Letters; vol. 59; 44; (2018); p. 3958 – 3960;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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, Computed Properties of C8H4BrNO2

To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added MeI (15 mL, 241 mmol) and K2CO3 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C. for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgSO4 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001-004.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; BINDER, Florian; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; VINTONYAK, Viktor; US2014/275025; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C9H6BrNO2

1-3.1 (397 mg, 1.65 mmol) and hydrazine hydrate (1 mL, 20.6 mmol) are heated to 100 C for 1 h and at 125 C for 1 h. To the cool reaction mixture DCM and water are added and the aqueous layer extracted twice with DCM. The combined organic layers are washed with brine, dried, concentrated and the residue purified via column chromatography (using solvent mixture cyclohexane / EA = 3:1). Yield 65%. m/z 226 [M+H]+, m/z 224 [M+H]-, rt 0.58 min, LC-MS Method b.

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; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GRUNDL, Marc; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; RIETHER, Doris; WIENEN, Wolfgang; WO2013/41497; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 99365-40-9, name is 6-Bromoindolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Bromoindolin-2-one

4 mmol of 6-bromo-2-indolone (XI) was dissolved in 20 ml of tetrahydrofuran solution, 4.8 m mol of sodium hydrogencarbonate was added, and then 8 mmol of di-tert-butyl dicarbonate was added, and the reaction system was stirred at 66 C. The reaction was quenched with TLC until the title material was evaporated. The mixture was evaporated to ethyl ether. Separation and purification with n-hexane:ethyl acetate = 5:1 as eluent gave 668 mg of white solid.The yield was 54%.

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; UNIV GUANGDONG TECHNOLOGY; Guangdong University of Technology; ZHUANG GUISHENG; Zhuang Guisheng; LIU YAN; Liu Yan; LU HANBIN; Lu Hanbin; HE HONGYUN; He Hongyun; MARUOKA HIROJI; Wan Gangqier; (32 pag.)CN108299491; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 6326-79-0, name is 6-Bromoisatin, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4BrNO2

The 1.15g (5mmol) 6- bromo-isatin was dissolved in 10mL DMF,1.03 g (7.5 mmol) of potassium carbonate was added with stirring.Then, 0.804 g (6.25 mmol) of dimethyl sulfate was added dropwise, and the mixture was reacted at room temperature for 4 hours, and the mixture was poured into 100 mL of ice water.The extract was extracted with ethyl acetate (60 mL×3), and the organic layer was evaporated.After concentrated to dryness, it was purified by silica gel column chromatography ( petroleum ether: ethyl acetate = 20:3)0.753 g of a red solid was obtained in a yield of 63%.

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong University; Li Xun; Yu Haipeng; Zheng Yongtang; Huang Xusheng; (15 pag.)CN110183372; (2019); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Bromoisatin

A mixture ofZn power (8.64g, 132.13mmol) and TiCl4 (12.60g, 66.42mmol) in THF (100mL) was stirred at 80 C for 2 hours, then it was cooled to RT, a solution of 4-bromoindoline-2, 3-dione (5.01g, 22.16mmol) in THF (100mL) was added dropwise under N2. After completion of the reaction, Hydrochloric acid solution (100mL, 3M) was added, the mixture was extracted with DCM (50mL3), the organic phase was washed with brine (50mL2), dried over anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure, the residue was purified by column chromatography to afford the compound 9a (2.63g, 56.0%). MS: 212 (M+H) +.

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 20780-72-7.

Reference:
Patent; JACOBIO PHARMACEUTICALS CO., LTD.; MA, Cunbo; GAO, Panliang; CHU, Jie; WU, Xinping; WEN, Chunwei; KANG, Di; BAI, Jinlong; PEI, Xiaoyan; (82 pag.)WO2017/211303; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 15362-40-0, The chemical industry reduces the impact on the environment during synthesis 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, I believe this compound will play a more active role in future production and life.

Pyrrole-2-carboxaldehyde (1 mmol) was treated with benzyl bromide (1.5 mmol) in the presence of NaH (1.5 mmol) in DMF (solvent) at 0 C for 15 min, the progress of the reaction was monitored with TLC and the reaction was shifted to room temp for another 15 min. After completion, the reaction was quenched by adding water and the crude product was isolated by extraction with ethyl acetate (2 x 50 ml), the organic layers were combined, dried over Na2SO4 and distilled in vacuum to give N-benzylpyrrole-2-carboxaldehyde (A) which was further purified by column chromatography using ethyl acetate: hexane (1:50). N-benzylpyrrole-2-carboxaldehyde (A, 1 mmol) was reacted with 1-(2,6-dichlorophenyl)-2-indolinone (1.2 mmol) in the presence of piperidine (0.2 mmol) in CHCl3/ DMF under microwave irradiations at 100 C for 1h. The progress of the reaction was monitored with TLC. After completion, the reaction was worked up by adding water and extraction with chloroform (2 x 50 ml). Combined organic layers were dried over Na2SO4 and distilled in vacuum to give crude product 3a which was purified by column chromatography using ethyl acetate:hexane (3:50) as eluent. Yellow Solid, yield 62%, mp 153-155 C; IR (KBr): 3059, 2925, 1695, 1599, 1485, 1365; 1H NMR (500 MHz, CDCl3, 25 C, TMS) delta: 5.41 (s, 2H, CH2), 6.40-6.41 (m, 2H, ArH), 7.04 (t, 1H, J = 7.5 Hz, ArH), 7.07 (s, 1H, ArH), 7.13 (t, 1H, J = 7.6 Hz, ArH), 7.19 (d, 2H, J = 7.4 Hz, ArH), 7.29-7.34 (m, 2H, ArH), 7.36-7.41 (m, 3H, ArH), 7.47 (s, 1H, =CH), 7.52 (d, 2H, J = 8.09 Hz, ArH), 8.49 (dd, 1H, J = 4.13 Hz, 1.29 Hz, ArH); 13C NMR (125 MHz, CDCl3, normal/DEPT-135) delta: 51.3 (-ve, CH2), 108.6 (+ve, CH), 110.7, (+ve, CH), 117.1 (ArC), 117.8 (+ve,CH), 121.9 (+ve, CH), 122.1 (+ve, CH), 123.0 (+ve, CH), 125.2 (ArC), 126.2 (+ve, CH), 126.9 (+ve, CH), 127.1 (+ve, CH), 128.0 (+ve, CH), 128.7 (ArC), 128.8 (+ve, CH), 128.9 (+ve, CH), 129.1 (+ve, CH), 129.2 (+ve, CH), 130.1 (+ve, CH), 131.4 (ArC), 135.9 (ArC), 137.3 (ArC), 139.2 (ArC), 164.8 (C=O); HRMS (ESI) m/z for C26H18Cl2N2O [M+H]+ calcd. 445.0868, found 445.0817.

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, 1-(2,6-Dichlorophenyl)-2-indolinone, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kaur, Jagroop; Kaur, Baljit; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 28; 2; (2018); p. 129 – 133;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., Product Details of 6941-75-9

Step 1. 5-Bromo-3-hydroxyisoindoline-l-one (BI25): A mixture of Zn powder (1.73 g, 26.154 mmol), copper (II) sulfate pentahydrate (0.02 g ,0.08 mmol) and 2M aq NaOH (27 mL) were cooled to 0 C. 5-Bromoisoindoline-l,3-dione (5 g, 22mmol) was added at the same temperature over the period of 30 min. The reaction mixture was stirred at 0 C for 30 min and 3 h at RT. The reaction mixture was filtered and the filtrate was neutralized with concentrated HC1. The reaction mixture was diluted with ethanol and extracted with ethyl acetate. The combined ethyl acetate layer was dried over Na2S04 and concentrated under reduced pressure to afford the crude title compound as a brown solid, which was used in the next step without further purification (1.3 g): mp 258-261C; ]H NMR (400 MHz, DMSO-d6) delta 9.03 (br, 1H), 7.81 (m, 2H), 7.69 (m, 1H), 6.44 (m, 1H), 5.88 (d, J = 9.3 Hz, 1H); ESIMS m/z 225.83 ([M-H]”); IR (thin film) 1684, 3246, 606 cm”1.

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; DOW AGROSCIENCES LLC; LO, William C.; HUNTER, James E.; WATSON, Gerald B.; PATNY, Akshay; IYER, Pravin S.; BORUWA, Joshodeep; WO2014/100163; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7477-63-6, 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. 7477-63-6, name is 7-Chloroisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A magnetically stirred mixture of naphthalene-2-amine (1.0mmol), isatin (1.0 mmol), dialkyl acetylenedicarboxylate (1.2 mmol) andanhydrous antimony trichloride (0.10 mmol) in dry acetonitrile (3 mL) taken in a 10 mL round bottom flask fitted with a reflux condenser under argonatmosphere and was refluxed for 5 h. After completion of the reaction, the reaction mixture was allowed to cool, quenched with water (10 mL) and extracted with DCM (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and volatiles were removed in vacuo. The crude residue was purified by column chromatography over silica gel (100-200mesh), eluting with 25 percent ethyl acetate in petroleum ether to afford compound (4).

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

Reference:
Article; Karmakar, Rajiv; Kayal, Utpal; Bhattacharya, Biswajit; Maiti, Gourhari; Tetrahedron Letters; vol. 55; 7; (2014); p. 1370 – 1372;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 19727-83-4,Some common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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 61 5-(6-(6-nitroindoline-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydrospiro[indene-2,3′-pyrrolo-[2,3-b]pyridin]-2′(1’H)-one 150 mg (0.37 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid-hydrochloride, 60 mg (0.37 mmol) 4-nitroindole, 0.15 mL (0.87 mmol) DIPEA and 130 mg (0.41 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. Then the reaction mixture was diluted with water/MeOH, the precipitate formed was suction filtered and washed with plenty of water. The precipitate was dried. Yield: 165 mg (74% of theory) ESI-MS: m/z=520 (M+H)+ Rt (HPLC-MS): 1.56 min (method C)

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/21500; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem