Month: May 2021

Related Products of 201940-08-1,Some common heterocyclic compound, 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (200 mg, 0.67 mmol), Pd (OAc) 2 (30 mg, 0.2 equiv), DPPP (55 mg, 0.2 equiv), TEA (0.93 mL, 10 equiv) and MeOH : DMSO (1: 1,4 mL) was stirred for 16 h under CO (balloon) at 80 C. LC-MS and TLC (20% EtOAc-Hexane) showed completion of the reaction. The Reaction mixture was concentrated to remove MeOH and diluted with EtOAc (10 mL), and washed with water (2 x 25 mL). The organic layer was dried (Na2S04), concentrated and purified by silica gel column chromatography (eluent = 20% EtOAc-Hexane), giving pure 1, 3-dihydro-isoindole-2,5- dicarboxylic acid 2-tert-butyl ester 5-methyl ester (150 mg, 81 %). MS (APCI+) : m/z 178.1 (MH+-Boc).

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

Reference:
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA INC.; WO2005/37214; (2005); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

954-81-4, name is N-(5-Bromopentyl)phthalimide, 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. HPLC of Formula: C13H14BrNO2

General procedure: To a stirred solution of 2-5 (5 mmol) in THF (60 mL) was added potassium thioacetate (15 mmol), and the mixture was refluxed for 3-4 h. And the solvent was evaporated to dryness in vacuo, and then added water (30 mL), and the organic materials were extracted with EtOAc (3×30 mL). The combined extracts were washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc:petroleum ether=1:8) to give compounds 6-9 as white powder.

The synthetic route of 954-81-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hu, Kun; Qi, Yan-Jie; Zhao, Juan; Jiang, He-Fei; Chen, Xin; Ren, Jie; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 529 – 539;,
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. 2058-74-4, name is 1-Methylisatin, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Methylisatin

A solution of N-methylisatin (322 mg, 2.0 mmol), indole (258 mg, 2.2 mmol), and K2CO3 (138 mg, 1.0 mmol) in aqueous DMF (H2O/DMF, 2:1, 5.0 mL) was heated to 50 oC for 3 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 1:1), 3-hydroxy-3-(1H-indol-3-yl)-1-methylindolin-2-one (1m) was obtained as a white solid, 340 mg (61%).1 To a stirred solution of 1m (278 mg, 1.0 mmol) in DMF (3.0 mL) was added t-BuOK (125 mg, 1.1 mmol) and iodomethane (158 mg, 1.1 mmol) successively at 0 oC. The reaction mixture was stirred at room temperature for 2 h. After aqueous extractive workup and column chromatographic purification process (n-hexane/EtOAc, 3:1), compound 1a was obtained as a white solid, 185 mg (63%).

According to the analysis of related databases, 2058-74-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Seo, Da Young; Roh, Hwa Jung; Jo, Hwi Yul; Cho, Sung; Kim, Jae Nyoung; Tetrahedron Letters; vol. 59; 11; (2018); p. 1005 – 1009;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. HPLC of Formula: C9H11N

General procedure: To a solution of compound77(0.40g, 1.35mmol) in dioxane (2mL) were added indoline (0.3mL, 2.70mmol), triethylamine (0.37mL, 2.70mmol), and 4-dimethylaminopyridine (0.16g, 1.35mmol). The mixture was purged with nitrogen for 2min. ThenPd (dppf)Cl2.CH2Cl2 (0.11g, 0.14mmol) and Mo(CO)6(0.18g, 0.68mmol) were added and the mixture was sealed in a microwave tube and heated to 85C overnight.The reaction was monitored by TLC. Upon completion, the reaction was cooled to room temperature, and diluted with water, and extracted with EtOAc (3*20mL). The combined organic fractions were washed with brine, dried over Na2SO4, and concentrated by evaporation under reduced pressure. Purification by silica gel column chromatography (gradient elution, gradient 0 to 25% EtOAc/60-90C petroleum ether) gave compound43as a light red solid (0.38g, 1.05mmol, 78% yield).

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

Reference:
Article; Hu, Jianping; Wang, Yingqing; Li, Yanlian; Cao, Danyan; Xu, Lin; Song, ShanShan; Damaneh, Mohammadali Soleimani; Li, Jian; Chen, Yuelei; Wang, Xin; Chen, Lin; Shen, Jingkang; Miao, Zehong; Xiong, Bing; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 156 – 175;,
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. 20870-79-5, name is 5-Nitroindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Nitroindolin-2-one

Di-tert-butyl dicarbonate (5.51 g, 25.27 mmol) and sodium hydrogen carbonate (12.73 g, 151.65 mmol) were added to a stined solution of 5-nitroindolin-2-one (3.0 g, 16.85 mmol) in tetrahydrofuran (150 mL) and the mixture was heated to 60 C. After 3h the reaction mixture was cooled and filtered, the filtrate was concentrated in reduced pressure to obtain a crudecompound. The obtained crude was purified by silica gel chromatography using a mixture of10% ethyl acetate/hexane as an eluent to get the desired compound as a white solid (3.68 g,5 1%). ?H-NMR (300 MHz, DMSO- d6) oe 8.3 (m, 1H), 8.2 (s, 1H), 7.9 (m, 1H), 3.8 (s, 2H), 1.5(s, 9H); LC-MS: m/ LC-MS: 278.8 (M+H).

The synthetic route of 20870-79-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; UJJINAMATADA, Ravi Kotrabasaiah; SAMAJDAR, Susanta; HOSAHALLI, Subramanya; ABBINENI, Chandrasekhar; (70 pag.)WO2018/109650; (2018); A1;,
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. 59-48-3, name is Indolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 59-48-3

(a) Nitration of 6.66 g. oxindole in 25 ml. conc. sulfuric acid with 2.1 ml. fuming nitric acid is conducted according to the procedure of W. C. Sumpter et al., J. Amer. Chem. Soc. 67, 499 (1945). Crystallization of the crude product from 50% acetic acid and from methanol yields 3.85 g. 5-nitrooxindole, m.p. 240-242. (Sumpter et al. recorded m.p. 240-241).

According to the analysis of related databases, 59-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; American Home Products Corporation; US4118561; (1978); A;,
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. 52351-75-4, name is 6-Methoxyindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H7NO3

A solution of 6-methoxyindoline-2,3-dione (1 g, 5.64 mmol, SCRC) in anhydrousN,N-dimethylformamide (40 mL) was cooled to 00 C, whereupon NaH (60 % dispersion inmineral oil, 0.264 g, 6.60 mmol) was added in one portion and the reaction was stirred for 5minutes. lodomethane (0.4 13 mL, 6.60 mmol) was added and the reaction was stirred at 0 Cfor 30 minutes. The mixture was then poured into saturated aqueous NH4C1 and extractedwith ethyl acetate. The combined organic portions were washed with water and brine, dried (MgSO4), filtered, and concentrated to give the crude product (1.079 g), which was used without further purification.

The synthetic route of 52351-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBVIE INC.; ABBVIE PHARMACEUTICAL TRADING (SHANGHAI) CO., LTD.; HARDEE, David; BREWER, Jason; HASVOLD, Lisa; LIU, Dachun; MCDANIEL, Keith; SCHRIMPF, Michael; SHEPPARD, George; (139 pag.)WO2018/188047; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 20870-79-5,Some common heterocyclic compound, 20870-79-5, name is 5-Nitroindolin-2-one, molecular formula is C8H6N2O3, 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.

Preparation of 5-amino-oxindole (2) To a solution of 5-nitro-oxindole (25 g) in 120 mL of dimethylacetamide in a Parr bottle was added 10% Pd/C (0.5 g). The mixture was hydrogenated (40 psi H2) for 16 hours. The catalyst was removed by filtration and the filtrate was diluted with ether (2 L) to provide 5-amino-oxindole (10.5 g; 50%).

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

Reference:
Patent; Pfizer Inc; US2005/256145; (2005); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 141452-01-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 141452-01-9 name is Methyl indoline-5-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

(R)-l-(4-cyclopentyl-3-ethyl-l-methyl-2-oxo-l,2,3,4-tetrahydropyrido[2,3-6]pyrazin-6- yl)indoline-5-carboxylic acid (i?)-6-chloro-4-cyclopentyl-3-ethyl-l-methyl-3,4-dihydropyrido[2,3-]pyrazin- 2(lH)-one (20.2 mg, 0.0688 mmol, 1 eq), methyl indoline-5-carboxylate (14.6 mg, 0.0825 mmol, 1.2 eq), Pd2dba3 (3.2 mg, 0.00344 mmol, 5 mol%), XPhos (4.9 mg, 0.0103 mmol, 15 mol%) and K2C03 (38 mg, 0.275 mmol, 4 eq) were dissolved in tBuOH (0.69 mL, 0.1 M) and heated to 100 C for 18 hours. The mixture was filtered through celite, washed with DCM/EtOAc/MeOH and condensed. Purification by column chromatography (ISCO, 4 g silica column, 0-10%MeOH/DCM, 15 minute gradient) gave a mixture of the desired methyl ester and the (inconsequential) ethyl ester, which was used without further purification (29.64 mg). LCMS 434.48 (M+H), 449.47 (ethyl ester M+H). The resulting material was dissolved in THF (0.34 mL) and water (0.17 mL). LiOH (2.4 mg) was added and the mixture was stirred at room temperature. Due to poor solubility and sluggish conversion, an additional 2.4 mg LiOH, 0.17 mL water and 0.17 mL MeOH were added. After 2 days, the mixture was diluted with MeOH and purified by preparative HPLC to give a dark brown oil (16.78 mg, 0.0399 mmol, 59% over 2 steps. 1H NMR (400 MHz, Chloroform-;/) delta 8.10 (d, J= 8.6 Hz, 1H), 7.83 (dd, J= 8.6, 1.7 Hz, 1H), 7.79 – 7.74 (m, 1H), 7.16 – 7.1 1 (m, 1H), 6.21 (d, J= 8.4 Hz, 1H), 4.62 – 4.54 (m, 1H), 4.13 – 4.00 (m, 3H), 3.31 – 3.30 (m, 3H), 3.20 (t, J = 8.7 Hz, 2H), 2.14 – 2.04 (m, 2H), 1.80 – 1.54 (m, 8H), 0.86 (td, J = 7.6, 2.8 Hz, 3H). LCMS 421.51 (M+H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl indoline-5-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James, E.; GRAY, Nathanael; QI, Jun; MCKEOWN, Michael, R.; BUCKLEY, Dennis; WO2015/117055; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 20870-90-0, The chemical industry reduces the impact on the environment during synthesis 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, I believe this compound will play a more active role in future production and life.

A mixture of 5-bromo-N-methyloxindole(5 g, 22 mmol) and POCl3 (40 mL) was stirred and refluxed for 2h. After cooling, themixture was poured into ice water, and then extracted with dichloromethane (MC) forthree times. The combined organic layers were dried over anhydrous magnesium sulfate,filtered, and concentrated. The solid was washed with MC, white solid NMT (2.6 g) wasprepared. Yield was 61%.1H-NMR (300MHz, THF) delta(ppm) : 8.58 (s, 3H), 7.63-7.60 (d, 3H), 7.57-7.53 (d, 3H),4.40 (s, 9H).

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-Bromo-1-methyl-2-oxoindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kang, Hyeonmi; Lee, Hayoon; Shin, Hwangyu; Kang, Seokwoo; Kim, Beomjin; Park, Jongwook; Molecular Crystals and Liquid Crystals; vol. 618; 1; (2015); p. 47 – 54;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem