Author: Jessica.F

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. 19727-83-4, name is 6-Nitroindoline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8N2O2

To a solution of 6-nitroindoline (13) (590 mg, 3.6 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (860 mg, 4.3 mmol) in acetic acid (10.0 mL) was added sodium triacetoxyborohydride (1.14 g, 5.4 mmol) at 0C and the reaction mixture was stirred for 1 hr at this temperature and then heated to room temperature overnight. After the reaction completed, water was added to the the mixture and the mixture was extracted with CH2Cl2. The organic phase was washed with water and saturated NaHCO3, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to afford the crude product, which was purified by column chromatography to give the tert-butyl 4-(6-nitroindolin-1-yl) piperidine-1-carboxylate (14) 0.92 g, yield: 73.6%. 1H NMR (400 MHz, DMSO-d6) delta 8.77 (s, 1H), 7.89 (d, J = 8.1 Hz, 1H), 7.47 (d, J = 8.1 Hz, 1H), 4.20 (t, J = 8.5 Hz, 2H), 3.29(m, 4H), 3.26 (t, J = 8.5 Hz, 2H), 2.93(m, 1H), 2.20(m, 3H), 1.67(m, 1H), 1.38(m, 9H). MS (ESI) m/z: 348 [M+H]+.

According to the analysis of related databases, 19727-83-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tian, Jinlong; Sun, Nannan; Yu, Mingcheng; Gu, Xianfeng; Xie, Qiong; Shao, Liming; Liu, Jin; Liu, Li; Wang, Yonghui; European Journal of Medicinal Chemistry; vol. 167; (2019); p. 37 – 48;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 86626-38-2,Some common heterocyclic compound, 86626-38-2, name is 4-Bromoindoline, molecular formula is C8H8BrN, 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 above obtained 4-bromoindoline (759 mg, 3.81 mmol), and (Boc)2O (976 mg, 4.48 mmol) in MeCN (8 mL) was stirred at room temperature overnight. After evaporated, the residue was dissolved in ethyl acetate (40 mL), washed with water (3¡Á20 mL) and brine (1¡Á20 mL). The organic layer was concentrated and purified by column chromatography on silica gel (petroleum ether) to give 0601-177 (840 mg, 74%) as a white solid. 1H-NMR (400 MHz. DMSO-d6) delta 1.50 (s, 9H), 3.02 (t, J=8.8 Hz, 2H), 3.94 (t, J=8.8 Hz, 2H), 7.12 (m, 2H), 7.56 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromoindoline, its application will become more common.

Reference:
Patent; Curis, Inc.; Bao, Rudi; Lai, Chengjung; Qian, Changgeng; US2013/102595; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-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 2058-72-2, Application In Synthesis of 5-Bromo-1-methylindoline-2,3-dione

General procedure: To a solution of an alkyne 2 (1.2 equiv) in anhydrous toluene (3 mL) under an argon atmosphere, KOtBu (1.0 equiv) was added, and the mixture was stirred for 10-15 min. Then, an N-protected isatin 1 (1.0 equiv) was added to the reaction mixture, which was stirred for 30 min to 3 h until all the isatin was consumed (confirmed by TLC). The reaction was finally quenched with a few drops of 1 N HCl and the resulting mixture was extracted with CH2Cl2 (2 ¡Á 15 mL). The combined organic phases were washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was then purified by column chromatography on silica gel (EtOAc-hexane,10:90 to 30:70) to give compounds 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Dhara, Kalyan; Kapat, Ajoy; Ghosh, Tridev; Dash, Jyotirmayee; Synthesis; vol. 48; 23; (2016); p. 4226 – 4268;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 17826-05-0, name is 5,6-Dibromoindoline-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 17826-05-0, Formula: C8H3Br2NO2

To a solution of 1 (0.327) in THF (10 ml) a solution of 1 M BH3¡¤THF (2.5 equiv) was added dropwise at 0 C, then the mixture was stirred at rt for 3 h. After this time, the reaction was quenched by slowly adding 2 ml of demineralized water, then 2N HCl was added to pH 3. THF was removed under reduced pressure and the aqueous residue extracted with two portions of EtOAc. The organic layers were washed with two portions of brine, dried over Na2SO4 and evaporated under reduced pressure to give a yellow oil. The crude product was purified by silica gel chromatography (petroleum benzene/Et2O 9:1) to give the pure product 2 as a greyish crystalline solid, mp = 154-155 C, Rf = 0.2 (Et2O/petroleum ether 1:5), 68%. 1H NMR, 300 MHz, DMSO-d6 delta = 6.42 (1H, m, H3), 7.42 (1H, t, H2), 7.75 (1H, s, H7), 7.93 (1H, s, H4), 11.35 (1H, brs, NH). 13C NMR, 75 MHz, DMSO-d6 delta = 101.53, 113.62, 115.45, 116.71, 124.96, 128.76, 129.44, 136.35.

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, 5,6-Dibromoindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Mollica, Adriano; Stefanucci, Azzurra; Feliciani, Federica; Lucente, Gino; Pinnen, Francesco; Tetrahedron Letters; vol. 52; 20; (2011); p. 2583 – 2585;,
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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H9Cl2NO

Refluxed the reaction mixture of 5- (2-chloroethyl)-6-chloro oxindole (100 GM), 3- (1-piperazinyl)-1, 2-benzisothiazole (104.7 gm), sodium carbonate (92.2 gm), sodium iodide (6.4 gm), tetra butyl ammonium bromide (28 gm) and cyclohexane (1000 mL) till the reaction was completed. The reaction mass was cooled to a temperature of 30C and the solid was filtered. To the wet compound was added water (1000 mL) and continued stirring for 45 minutes. The solid was filtered and washed with water (100 mL). To the water wet compound was added acetone (500 mL) and there was stirring for 2 hours at room temperature. The compound was filtered and washed with acetone (200 mL) and dried at a TEMPERATURE OF70-75C to afford the CRUDE Ziprasidone base (156.9 g)

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY’S LABORATORIES LIMITED; DR. REDDY’S LABORATORIES INC.; WO2004/50655; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 19155-24-9, name is 3,3-Dimethylindolin-2-one, molecular formula is C10H11NO, 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: 19155-24-9

A solution of 3,3-dimethylindolin-2-one (1.5 g, 9.31 mmol)Was dissolved in tetrahydrofuran (90 mL)The solution was cooled to 0 C,To this was added borane-tetrahydrofuran (37.3 mL, 37.22 mmol).The reaction solution was refluxed at 87 C overnight,Cooled to room temperature and quenched with methanol (10 mL).The mixture was further refluxed at 85 C for 2 hours, after which it was concentrated under reduced pressure.The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 20/1)The title compound was obtained as a yellow oil (0.87 g, 63.5%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 19155-24-9, its application will become more common.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Ruyong; Wang Liang; (112 pag.)CN104016979; (2017); B;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1914-02-9, A common heterocyclic compound, 1914-02-9, name is 3,3-Dimethylindoline, molecular formula is C10H13N, 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 suspension of NaHC03 (5.41 g, 64.39 mmol) and 3,3-dimethylindoline (0.79 g, 5.37 mmol) in DCM (10 mL) was added acetyl chloride (0.76 mL, 10.73 mmol) dropwise at 0 C. The reaction was stirred at rt for 2 h, then filtered. The filtrate was concentrated in vacuo to give the title compound as a white solid (0.99 g, 97.1%). MS (ESI, pos. ion) m/z: 190 [M + H]+; NMR (CDCI3) delta (ppm): 8.11 (d, 1H), 7.13 (t, 1H), 7.06 (d, 1H), 6.97 (t, 1H), 3.70 (s, 2H), 2.15 (s, 3H), 1.29 (s, 6H).

The synthetic route of 1914-02-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CALITOR SCIENCES, LLC; SUNSHINE LAKE PHARMA CO., LTD; XI, Ning; WANG, Ruyong; WANG, Liang; WO2014/89324; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 205383-87-5, The chemical industry reduces the impact on the environment during synthesis 205383-87-5, name is tert-Butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, I believe this compound will play a more active role in future production and life.

To tert-butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, purchased from Zerenex (50.0 mg, 0.17 mmol) in acetonitrile (1.5 mL) is added N-bromosuccinimide (30.5 mg, 0.17 mmol) and the reaction mixture is stirred for 5 h at r.t. The reaction mixture is diluted with water and saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer is washed with brine, dried and concentrated in vacuo. Yield 80%, m/z 367; 369 [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, tert-Butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; VINTONYAK, Viktor; GRAUERT, Matthias; GRUNDL, Marc; PAUTSCH, Alexander; (64 pag.)US2016/75704; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, molecular formula is C14H9Cl2NO, 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. COA of Formula: C14H9Cl2NO

Pyrrole-2-carboxaldehyde (1 mmol) and 1-(chloromethyl)naphthalene (1.5 mmol) were exposed to react in the presence of NaH (1.5 mmol) in DMF (solvent) at 0 – 25 C for 45 min, the progress of the reaction was monitored with TLC. After completion, the reaction was quenched by the addition of water and the product was extracted with ethyl acetate (2 x 50 ml). The organic layers were combined, dried over Na2SO4 and distilled in vacuum to give 1-(naphthalen-1-ylmethyl)-1H-pyrrole-2-carbaldehyde (A) which was purified by column chromatography using ethyl acetate: hexane (2:48). 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 extracted with chloroform (2 x 50 ml). Combined organic layers were dried over Na2SO4 and distilled in vacuum to procure crude product 3d which was further purified by column chromatography using ethyl acetate: hexane (2:50) as eluent to get two inseparable isomers (1:2 1H NMR spectrum). Yellow Solid, yield 68 %, mp 180-182 C; IR (KBr): 2853, 3066, 1699, 1598, 1484, 1391; 1H NMR (500 MHz, CDCl3) delta: 5.78 (s, 2H, CH2 maj), 5.87 (s, 2H, CH2 min), 6.39-6.46 (m, 4H, 2ArHmaj + 2ArHmin), 6.83-6.84 (m, 1H, ArHmaj), 6.90-6.94 (m, 1H, ArHmin), 6.96 (d, J = 6.8 Hz, 1H, ArHmin), 7.0-7.01(m, 1H, ArHmin), 7.02 (d, J = 6.8 Hz, 1H, ArHmaj), 7.07-7.17 (m, 3H, 1ArHmaj + 2ArHmin), 7.21-7.24 (m, 1H, ArHmaj), 7.35-7.40 (m, 3H, 2ArHmaj + 1ArHmin), 7.41-7.45 (m, 2H, 1ArHmaj + 1ArHmin), 7.47 (s, 2H, ArHmin), 7.51(d, J = 8.0 Hz, 3H, 2ArHmaj+1ArHmin), 7.54-7.58 (m, 3H, 2ArHmaj + 1ArHmin), 7.60-7.68 (m, 2H, 1ArHmin), 7.84-7.87 (m, 3H, 2ArHmaj + 1ArHmin), 7.91-7.93 (m, 2H, ArHmaj), 7.98 (d, J = 7.78 Hz, 1H, ArHmin), 8.06 (d, J = 8.32 Hz, 1H, ArHmin), 8.35 (d, J = 7.75 Hz, 1H, ArHmaj), 8.55-8.56 (m, 1H, ArHmin); 13C NMR (125 MHz, CDCl3) delta:48.7, 49.0, 108.6, 109.0, 110.3, 110.9, 116.4, 117.3, 117.9, 120.8, 121.9, 122.0, 122.10, 122.13, 122.4, 122.5, 122.6, 122.7, 124.8, 125.0, 125.4, 125.6, 125.8, 126.1, 126.2, 126.8, 126.9, 127.1, 127.3, 128.5, 128.7, 128.75, 128.8, 128.9, 129.0, 129.1, 129.2, 130.2, 130.4, 130.5, 130.7, 130.8, 131., 132.1, 132.4, 133.6, 135.8, 136.0, 139.2, 141.3, 164.9, 167.8; HRMS (ESI) m/z for C30H20Cl2N2O [M+H]+ calcd. 495.1025, found 495.1041.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15362-40-0, its application will become more common.

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. 6341-92-0, name is 6-Chloroisatin, A new synthetic method of this compound is introduced below., Computed Properties of C8H4ClNO2

General procedure: To a pyrex reaction vessel containing a solution of isatin 1a (147 mg, 1.0 mmoL) and NaAuCl4.2H2O (7.95 mg, 2 mol%) in EtOH (1 mL) was added 4-hydroxycoumarin 2 (324 mg, 2.0 mmoL). The resulting mixture was stirred at 40 C for 15 min under microwave irradiation (power level of 200 W). After completion of the reaction as evidenced by TLC, the mixture was cooled to room temperature and poured into ice-cold water (10 mL). The solid obtained was collected by filtration and washed with copious amount of cold water and dried under vacuum at 40 oC for 15 min to afford 251 mg of analytically pure product 3a.

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:
Article; Parthasarathy; Praveen, Chandrasekar; Jeyaveeran; Prince; Bioorganic and Medicinal Chemistry Letters; vol. 26; 17; (2016); p. 4310 – 4317;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem