Month: August 2021

Reference of 6872-06-6, These common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, 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 19b Synthesis of (+)-2-[2-(2-methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin(D4)-4-yl-3H-pyrimidin-4-one and example 20b: (-)-2-[2-(2-methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-(2,2,6,6-morpholin-D4)-4-yl-3H-pyrimidin-4-one Step 1b: Synthesis of 2-(4-chloro-6-methoxpyrimidin-2-yl)-1-(2-methyl-2,3-dihydroindol-1-yl)ethanone In a three-necked flask, under argon, 4 g of the sodium salt of (4-chloro-6-methoxypyrimidin-2-yl)acetic acid (example 8b, step 3b) and 2.6 g of 2-methylindoline (6872-06-6, Aldrich) are placed in 3 ml of pyridine and 60 ml of DMF. The heterogeneous solution obtained is stirred at ambient temperature (20 C.), then N-[3-(dimethylamino)propyl]-N?-ethylcarbodiimide hydrochloride is added and stirring is maintained for 20 hours. The reaction mixture is concentrated in a rotary evaporator under vacuum, 100 ml of water are added, extraction is carried out with 3 times approximately 50 ml of dichloromethane, washing is carried out with 50 ml of saturated NaCl solution, drying is carried out over MgSO4 and filtration is carried out through a VF filter. The compound obtained is chromatographed on silica gel (40-63 mum), elution being carried out with dichloromethane. The fractions containing the expected compound are combined and evaporated. The compound obtained is triturated from diisopropyl ether, filtration is carried out, and drying is carried out at 20 C. 2-(4-Chloro-6-methoxypyrimidin-2-yl)-1-(2-methyl-2,3-dihydroindol-1-yl)ethanone is isolated (2.6 g) in the form of a solid (yield 46%) which is used as it is in the next step.

Statistics shows that 2-Methylindoline is playing an increasingly important role. we look forward to future research findings about 6872-06-6.

Reference:
Patent; SANOFI; Brollo, Maurice; Carry, Jean-Christophe; Certal, Victor; Didier, Eric; Doerflinger, Gilles; EL Ahmad, Youssef; Filoche-Romme, Bruno; Halley, Frank; Karlsson, Karl Andreas; Schio, Laurent; Thompson, Fabienne; US2013/274253; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 2307-00-8, These common heterocyclic compound, 2307-00-8, name is 5-Amino-2-methylisoindoline-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.

A mixture of 1-phenylisatin (50 mg, 0.22 mmol) and 4-amino-N-methylpthalimide (40 mg, 0.22 mmol) was heated neat at 215 C. for 2 h. The crude material was purified by preparative TLC using a mixture of 3:7 ethyl acetate and hexane as the eluent, giving the desired product as a yellow solid (8 mg, 0.02 mmol, 10%). 1H NMR (400 MHz): delta 7.88 (d, J=7.8, 1H), 7.83-7.80 (m, 1H), 7.51 (t, J=7.5, 1H), 7.47-7.18 (m, 6H), 7.02 (t, J=8.0, 1H), 6.91-6.79 (m, 2H), 6.58 (d, J=7.5, 1H), 3.22 (s, 3H); ESI-MS m/z found 382 (MH+).

The synthetic route of 2307-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Blackburn, Thomas P.; US2007/135510; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 317-20-4, The chemical industry reduces the impact on the environment during synthesis 317-20-4, name is 7-Fluoroisatin, I believe this compound will play a more active role in future production and life.

Under nitrogen protection,4 g (0.024 mol) of 7-fluoro isatinAnd 3.52 g (0.093 mol) of sodium borohydride were put into a dry four-necked flask,Cooled to -10 C or less,Stirring,To this, 40 mL of dry tetrahydrofuran was slowly added dropwiseAnd 7.6 g (0.054 mol) of borontrifluoride etherate,The whole process control temperature does not exceed -5 ,Reaction overnight,Reaction completed,A solution of 6.6 g of sodium hydrogen sulfate and 70 mL of water was slowly added dropwise to the solution,Steam distillation mixture,The distillate was extracted with ethyl acetate,Dried over anhydrous magnesium sulfate,The solvent was distilled off,To give 2.58 g of white needles (yield 78.8%).

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

Reference:
Patent; Changzhou Vocational Institute of Engineering; Liu, Changchun; Cheng, Jin; Liu, Chengxian; Jiang, Ruoyu; Xu, Jin; Xue, Xuming; Zhou, Dongdong; (5 pag.)CN105732462; (2016); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-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. COA of Formula: C9H9NO2

A round bottom flask was charged with 3-(2-(4-methylpiperazin-l-yl)pyrimidin-5- yl)-lH-indazole-6-carbaldehyde (26 mg, 0.80 mmol), 5-methoxyoxindole (13 mg, 0.80 mmol), piperidine (0.8 uL, 0.008 mmol) and MeOH (2 mL). The reaction was then heated to 6O0C for 4 hrs. An orange precipitate formed which was further precipitated by cooling to room temperature. The orange solid was then filtered and washed with MeOH (5 mL) giving 9.8 mg, 26 % of the title compound. 1H NMR (400 MHz, de-DMSO) delta 13.46 (s, IH), 10.44 (s, IH), 8.97 (s, 2H), 8.18 (d, J = 8.5 Hz, IH), 7.94 (s, IH), 7.78 (s, IH), 7.48 (d, J = 8.8 Hz, IH), 7.20 (s, IH), 6.85 (d, J = 10.6 Hz, IH), 6.80 (d, J = 9.0 Hz, IH), 3.82 (br t, 4H), 3.59 (s, 3H), 2.39 (br t, 4H), 2.23 (s, 3H); MS ESI 468.3 [M + H]+, calcd for [C26H25N7O2 + H]+ 468.2.

The synthetic route of 5-Methoxyindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY HEALTH NETWORK; WO2009/79767; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 324-03-8, name is 6-Fluoroindoline-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 324-03-8, Product Details of 324-03-8

6-Fluoro-l-isopropyl-lH-indole-2,3-dione E-1.2′”” To a stirred solution of 6-Fluoro-lH-indole-2,3-dione E-1.2″”” (55.0 g; 333.1 mmol) in DMF (550 ml) is added K2C03 (55.2 g; 399.7 mmol) and 2-Iodo- propane (73.6 g; 433.0 mmol) at 25C. The reaction mixture is stirred at 25C for 16 h. Then the mixture is diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure to obtain crude compound. The crude was purified by column chromatography using silicagel (230-400 muMu) with eluting mixture of ethyl acetate and hexane. Yield: 51% (35.0 g; 169.0 mmol) HPLC-MS: (M+H)+ = 208; tRet = 2.02 min; method R D-FA-4.5-MIN

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ENGELHARDT, Harald; WO2015/169962; (2015); 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., Safety of 6-Bromoindolin-2-one

Preparation 1: 6-Iodooxindole A schlenk tube and stir bar were dried in an oven overnight and then were evacuated, filled with Ar(g) and cooled. The schlenk tube was charged with CuI (45 mg, 0.236 mmol, 5 mol %), 6-bromoxindole (1.0 g, 4.72 mmol), and NaI (1.42 g, 9.44 mmol). The schlenk tube was evacuated and backfilled with Ar(g) (3 times). Racemic trans-N,N’-dimethyl-1,2-cyclohexanediamine (74 muL, 0.472 mmol, 10 mol %) and anhydrous dioxane (4.72 mL) were added via syringe under Ar(g). The schlenk tube was sealed with a teflon valve and the suspension was stirred at 110 C. for 24 h. The reaction was then cooled to room temperature and 15% NH4OH(aq) (50 mL) was added to the reaction mixture while stirring. The suspension was allowed to stir for about 30 min after which the tan solid was vacuum filtered and dried affording 6-Iodooxindole in 84% yield (1.027 g, 3.96 mmol).

The synthetic route of 99365-40-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Allergan, Inc.; US2007/15748; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 64483-69-8 as follows. Recommanded Product: 64483-69-8

5-Acetyl-2-oxindole (2 g) in 15 mL trifluoroacetic acid in an ice bath was slowly treated with 1.8 g triethylsilane and then stirred at room temperature for 5 hours. One mL of riethylsilane was added and the stirring continued overnight. The reaction mixture was poured into ice water and the resulting precipitate collected by vacuum filtration, washed copiously with water and dried under vacuum to give 1.3 g (71% yield) of the title compound as a yellow solid. 1H-NMR (360 MHz, DMSO-d6): delta 10.25 (s, br, NH-1), 7.03 (s, 1 H, H-4), 6.97 (d, J=8.05 Hz, 1 H, H-6), 6.69 (d, J=8.05 Hz, 1 H, H-7), 3.40 (s, 2 H, CH2-3), 2.51 (q, J=7.69 Hz, 2 H, CH2CH3-5), and 1.12 (t, J=7.42 Hz, 3 H, CH2CH3-5).

According to the analysis of related databases, 64483-69-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6395734; (2002); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7147-90-2,Some common heterocyclic compound, 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, molecular formula is C8H4ClNO2, 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: Phthalimide 6a (148mg, 1mmol), 124 1,4-dibromobutane (1.080g, 5mmol), 12 potassium carbonate (276mg, 2mmol) was added to 115 acetone (3mL), and the reaction mixture was refluxed for 2h. After cooling to room temperature, the reaction mixture was purified by column chromatography using 125 PE: acetone (40:1) as eluent to give 126 7a (260mg, 92%) as a white solid.

The synthetic route of 7147-90-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xu, Mingshuo; Wang, Yu; Yang, Feipu; Wu, Chunhui; Wang, Zhen; Ye, Bin; Jiang, Xiangrui; Zhao, Qingjie; Li, Jianfeng; Liu, Yongjian; Zhang, Junchi; Tian, Guanghui; He, Yang; Shen, Jingshan; Jiang, Hualiang; European Journal of Medicinal Chemistry; vol. 145; (2018); p. 74 – 85;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 4702-13-0, 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. 4702-13-0 name is N-Phthaloylglycine, 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.

STEP A:; To a stirred solution of A/-phthaloylglycine (11.92 g, 58 mmol) indichloromethane (200 mL) at room temperature, oxalyl chloride (7.5 mL, 87mmol) was added. DMF (two drops) was then added. The resulting solutionwas concentrated after stirring four hours at room temperature.Dichloromethane (100 mL, dry) was then added to the residue. Benzylamine(9.5 mL, 87 mmol) was added slowly into the resulting solution. Triethylamine(12 mL, 87 mmol) was then added slowly into the solution. Dichloromethane(200 mL) and methanol (50 mL) were added 30 min after the completedaddition of triethylamine. The resulting solution was extracted with 2 N HCIsolution twice, 1 N NaOH solution one time and 1 N HCI one time, and thendried over MgSO4. The solution was filtered and concentrated to yield N-benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide as a white solid.MH+= 294.9.

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

Reference:
Patent; JANSSEN PHARMACEUTICA, N.V.; BAXTER, Ellen; BOYD, Robert; COATS, Steve; JORDAN, Alfonzo; REITZ, Allen; REYNOLDS, Charles H.; SCOTT, MALCOLM; SCHULZ, Mark; DE WINTER, Hans Louis Jos; WO2006/17844; (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. 181140-34-1, name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, A new synthetic method of this compound is introduced below., category: indolines-derivatives

General procedure: Compounds 3-7 have been synthesized using a procedure originally reported by Roehrig et al.16 Chiral amine or amino alcohol (0.6 mmol, 1.2 equiv) in 10 mL isopropanol was added to the solutionof (R)-N-(2,3-epoxypropyl)phthalimide (102 mg, 0.50 mmol)in 10 mL of isopropanol at in an ice bath and stirred for 1 h. then refluxed for 12 h. The reaction monitored by TLC. Solvent was removed by rotary evaporator under reduced pressure after completion of the reaction.

The synthetic route of 181140-34-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Karakaplan, Mehmet; Jameel, Basam; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 597 – 602;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem