Author: Jessica.F

Reference of 350797-56-7, 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. 350797-56-7 name is 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate, 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.

General procedure: Raw materials (II), hydrochloric acid added to the organic solvent, heated to a certain temperature, slowly adding zinc powder in batch, by thin layer chromatography (TLC) or high performance liquid chromatography (HPLC) to the raw material (II) completely react , The filter cake is washed with a solvent to the product (I), and then subjected to separation and purification by conventional means such as concentration, washing, drying,To give the salt of the compound (I), which is obtained by alkalizing the free base of (I).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate, and friends who are interested can also refer to it.

Reference:
Patent; Changzhou Ruiming Pharmaceutical Co., Ltd.; Shi Weiming; (5 pag.)CN106928118; (2017); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 2436-29-5, 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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, This compound has unique chemical properties. The synthetic route is as follows.

Example 26Synthesis of 2-(3-((7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)amino)propyl)isoindoline-1,3-dione (181) To a slurry of 4-(4-amino-6-methoxynaphthalen-2-yl)-N-methylpyrimidin-2-amine (150 mg, 0.42 mmol) in 1,2-dichloromethane (10 ml) was added N,N-diisopropylethylamine (250 mul) followed by acetic acid (0.5 ml), 3-(1,3-dioxoisoindolin-2-yl)propanal (140 mg) and sodium triacetoxyborohydride (200 mg). The mixture was stirred at room temperature for 24 hours before being poured into ethyl acetate (100 ml) washed with water (250 ml) and dried over anhydrous magnesium sulfate. Evaporation to dryness gave a yellow oil which was purified by silica gel chromatography eluting with 40-60% ethyl acetate in hexanes to yield 2-(3-((7-methoxy-3-(2-(methylamino)pyrimidin-4-yl)naphthalen-1-yl)amino)propyl)isoindoline-1,3-dione 181 as a yellow foam (95 mg). 1H NMR (CDCl3) 400 MHz delta 8.34 (d, J=5.2 Hz, 1H), 7.87 (s, 1H), 7.86-7.83 (m, 3H), 7.8 (d, J=8.8 Hz, 1H), 7.75-7.71 (m, 2H), 7.34 (s, 1H), 7.31 (d, J=2.4 Hz, 1H), 7.18 (dd, J=2.4 and 8.8 Hz, 1H), 7.08 (d, J=4.8 Hz, 1H), 5.24 (m, 1H), 4.9 (m, 1H), 4.04 (s, 3H), 3.9 (t, J=6.0 Hz 2H), 3.5 (t, J=6.0 Hz, 2H), 3.11 (d, J=5.2 Hz, 3H), 2.24 (m, 2H), 2.2-2.14 (m, 2H), LCMS m/e 468 (M+H)

The chemical industry reduces the impact on the environment during synthesis 3-(1,3-Dioxoisoindolin-2-yl)propanal. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ArQule, Inc.; US2011/166137; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 7477-63-6, A common heterocyclic compound, 7477-63-6, name is 7-Chloroisatin, molecular formula is C8H4ClNO2, 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.

In a 100 mL round bottom flask, according to the feed ratio (7-chloroisatin: benzyl alcohol (1:1.5); 7-chloroisatin: malondialdehyde (1:1.2))Add 7-chloroisatin 80 mg (0.44 mmol), benzyl alcohol 71.3 mg (0.66 mmol) and malondialdehyde 38.2 mg (0.53 mmol), respectively.Add a catalytic amount (0.1 times equivalent of 7-chloroisatin) of 001×7 MB, ferrocene and palladium acetate, 50 mL of solvent benzene, heat to 90 ° C, and heat the reaction for 6 hours.The reaction was monitored by thin layer chromatography. After the reaction was completed, the heating was stopped, the condensing device was removed, the mixed system was concentrated under reduced pressure, and purified by column chromatography.The target compound (14) was obtained by drying to give 115.8 mg (yield: 81percent).

The synthetic route of 7477-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaanxi University of Science and Technology; Liang Chengyuan; Tian Danni; Ding Shunjun; Wang Xuechuan; Dong Hao; Wang Qiang; (15 pag.)CN108395438; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 19727-83-4, A common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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.

Step A: 6-Nitroindoline (3.0 g, 18.3 mmol) was dissolved in THF (45 mL) and Et3N (3.4 mL, 24.4 mmol) at O0C. Acetyl chloride (1.5 mL, 21 mmol) was added drop wise. The mixture was stirred at room temperature for 30 minutes. The mixture was partitioned between EtOAc and aqueous HCl. The organic layer was dried and concentrated to yield l-acetyl-6-nitroindoline (3.8 g, 100%) as a yellow solid.

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; PTC THERAPEUTICS, INC.; HWANG, Peter Seongwoo; TAKASUGI, James; REN, Hongyu; WILDE, Richard Gerald; TURPOFF, Anthony; AREFOLOV, Alexander; KARP, Gary Mitchell; CHEN, Guangming; CAMPBELL, Jeffrey Allen; WO2006/19831; (2006); 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. 104618-31-7, name is 2-(4-Hydroxycyclohexyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., category: indolines-derivatives

190gms(0.7755mole) 4-phthalimido cyclohexanol are dissolve in 1480ml chloroform.Add solution of H2SO4 (435.87gm, 4.4476mole cone. H2SO4 was added in 900 mlwater). Cool mass to 25C,add lot wise 180.5gm(0.6139mole) potassium dichromate inone hour. Stir mass for three hours, add 900 ml water and separate organic phase.Organic phase was washed with water and 2% NaHCO3 solution, after drying andconcentration of extracts product was isolated by adding methanol and water mixture.YIELD: 175g(92.4%)PURITY: 96.01%.

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; ALEMBIC LIMITED; WO2006/3677; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 603-62-3, 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. 603-62-3, name is 3-Nitrophthalimide, This compound has unique chemical properties. The synthetic route is as follows.

To a solution of potassium hydroxide (16.1 g, 286 mmol) in water (500 mL), was added 3-nitrophthalimide (25.0 g, 130 mmol) in portion at 0 C. The suspension was stirred at 0 C for 3 hrs, and then heated to 30 C for 3 hrs. To the solution, was added HCl (100 mL, 6N). The resulting suspension was cooled to 0 C for 1 hr. The suspension was filtered and washed with cold water (2 x 10 mL) to give 3-nitro-phthalamic acid as a white solid (24.6 g, 90% yield): 1H NMR (DMSO-d6) 7.69 (brs, 1H, NHH), 7.74 (t, J = 8 Hz, 1H, Ar), 7.92 (dd, J = 1, 8 Hz, 1H, Ar), 8.13 (dd, J = 1, 8 Hz, 1H, Ar), 8.15 (brs, 1H, NHH), 13.59 (s, 1H, OH); 13C NMR (DMSO- d6) 125.33, 129.15, 130.25, 132.54, 136.72, 147.03, 165.90, 167.31.

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

Reference:
Patent; CELGENE CORPORATION; GANDHI, Anita; HAGNER, Patrick; KLIPPEL, Anke; POURDEHNAD, Michael; TROTTER, Matthew, William Burnell; LEI, Ming; (162 pag.)WO2017/24019; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 39603-24-2, 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. 39603-24-2, name is 5,7-Dimethylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of substituted isatins 1 (1mmol), sarcosine 2/1,3-thiazoles-4-carboxylic acid 5 (1 mmol) and Knoevenagel adduct (1 mmol) was refluxed for 10 min. in 2,2,2-trifluoroethanol (4 mL) under microwaves. All these reactions were carried out by microwave irradiation for 10 min at the power level 250 W and at the temperature of 150C which was recorded by the temperature probe of the microwave. Progress of the reaction was checked after a regular interval of one minute till the completion of reaction by TLC using hexane: ethylacetate (8:2) as mobile. Product was collected by the same way as in conventional methods. The TFE was distilled off (to recover for the next run). All the synthesized compounds were well characterized by IR, 1H NMR, 13C NMR, Mass and single crystal X-ray analysis.

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, 5,7-Dimethylindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Dandia, Anshu; Khan, Shahnawaz; Soni, Pragya; Indora, Aayushi; Mahawar, Dinesh Kumar; Pandya, Prateek; Chauhan, Chetan Singh; Bioorganic and Medicinal Chemistry Letters; vol. 27; 13; (2017); p. 2873 – 2880;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 102359-00-2, These common heterocyclic compound, 102359-00-2, name is 2-Oxoindoline-5-carboxylic Acid, 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 solution of 2-oxoindoline-5-carboxylic acid (0.200 g, 1.12 mmol), 1- [3- (dimethylamino) propyl] -3-ethylcarbodiimide hydrochloride (0.477 g, 2.47 mmol), diisopropylethylamine (0.586 mL, 3.37 mmol) and catalytic amount of N, N- dimethylaminopyridine in N, N-DIMETHYLFORMAMIDE/ACTEONITRILE (1: 1,4 mL) was added 2- methoxybenzylamine (0.295 mL, 2.26 mmol) and the reaction mixture stirred at room temperature for 1 h. The solvent was evaporated and the crude material was purified on a short silica gel column using dichloromethane containing 5% methanol as the eluent. This was followed by triturating from ethyl acetate to give 0.10 g (33% yield) of the yellow title compound : 1H NMR (DMSO-d6,400 MHz) 8 10.60 (br s, 1 H), 8.65 (t, J = 6 Hz, 1 H), 7.79-7. 77 (m, 2 1-1), 7.21 (t, J = 8 Hz, 1 H), 7.15 (d, 7= 8 HZ, 1 H), 6. 98 (d, J = 8 Hz, 1 H), 6.90-6. 84 (m, 2 H), 4.42 (d, J = 6 Hz, 2 H), 3.81 (s, 3 H), 3.53 (s, 2 H) ; MS (ES) m/z 297 (M++1), NILZ 295

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

Reference:
Patent; ASTRAZENECA AB; WO2005/27823; (2005); A2;,
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. 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1035235-27-8

Step 5: tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate A solution of tert-butyl 4-bromo-1,3-dihydro-2H-isoindole-2-carboxylate (0.80 mmol), bis(pinacolato)diboron (0.96 mmol) and potassium acetate (2.5 mmol) in DMF (4 mL) was degassed. To this solution was added PdCl2dppf (1:1 complex with DCM, 0.04 mmol). The reaction mixture was heated at 85 C. for 4 hr and then allowed to cool to rt and diluted with EtOAc. The solution was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate (0.64 mmol, 80%) as a white solid. LCMS: (FA) ES+346.

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 1035235-27-8.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); 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. 24566-79-8, name is N-(6-Bromohexyl)phthalimide, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C14H16BrNO2

To a stirred solution of compound 3-i (6.39 g, 20.3 mol) in DMF (60 mL) was added potassium thioacetate (2.78 g, 34.3 mmol) portion wise and stirred for 20 min at room temperature. After complete addition, the reaction mixture was stirred at room temperature for 30 min. Reaction progress was monitored by TLC; after completion the reaction mixture was quenched with ice-cold water (250 mL) and stirred for 1 h. The resultant precipitated was filtered, washed with water (100 mL) and dried in vacuo to afford 4-i as an off-white solid (5.8 g, 93.5%). LCMS: 306.20 (M+l).

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 24566-79-8.

Reference:
Patent; CV6 THERAPEUTICS (NI) LIMITED; SPYVEE, Mark; (500 pag.)WO2018/98206; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem