Tag: M.W=200-300

Related Products of 65435-04-3, 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 65435-04-3 as follows.

A suspension of 9.3 g of 5-chloroacetyl-2-oxindole was stirred in 90 mL pyridine at 80 to 90 C. for 3 hours then cooled to room temperature. The precipitate was collected by vacuum filtration and washed with 20 mL ethanol. The solid was dissolved in 90 mL 2.5N sodium hydroxide and stirred at 70 to 80 C. for 3 hours. The mixture was cooled to room temperature and acidified to pH 2 with 0.5 N hydrochloric acid. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown solid.

According to the analysis of related databases, 65435-04-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 169037-23-4, name is 5-(Trifluoromethoxy)indoline-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 169037-23-4, Product Details of 169037-23-4

Step 1 5-(Trifluoromethoxy)isatin (2.00 g, 8.65 mmol) was dissolved in 1N aqueous sodium hydroxide solution (150 mL) and aqueous hydrogen peroxide (30-35%, 2.45 mL) was added dropwise at room temperature to this solution. The reaction mixture was stirred at room temperature for 20 min., and adjusted to pH 3-4 by adding 1N hydrochloric acid. The precipitated insoluble material was collected by filtration, and washed with water to give 5-(trifluoromethoxy) anthranilic acid as a brown powder (1.88 g, 98%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Takeda Pharmaceutical Company Limited; Terauchi, Jun; Nara, Hiroshi; Oki, Hideyuki; Sato, Kenjiro; (166 pag.)US2015/329556; (2015); A1;,
Indoline – Wikipedia,
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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. 885272-46-8, name is tert-Butyl 4-bromoindoline-1-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C13H16BrNO2

A mixture of the product of Step 1 (1.5 g, 5.0 mmol), allyltributylstannane (2.48 g, 7.5 mmol) and Pd(PPh3)4 (0.58 g, 0.5 mmol) in toluene (20 mL) was stirred at 100 C overnight under a nitrogen atmosphere. The mixture was loaded directly to a silica gel loading cartridge and purified by silica gel column chromatography with EtOAc in hexanes (0 to 10% gradient) to give the title compound (0.88 g, 68%). 1H NMR (CDC13) delta: 7.76 (br. s, 1H), 7.15 (t, J=7.7 Hz, 1H), 6.80 (d, J=7.6 Hz, 1H), 5.88- 5.98 (m, 1H), 5.01-5.11 (m, 2H), 3.93-4.09 (m, 2H), 3.32 (d, J=6.3 Hz, 2H), 3.04 (t, J=8.7 Hz, 2H), 1.57 (s, 9H).

The synthetic route of 885272-46-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; WANG, Jiashi; GERASYUTO, Aleksey, Igorevich; ARNOLD, Michael, A.; KARP, Gary, Mitchell; QI, Hongyan; WOLL, Matthew, G.; ZHANG, Nanjing; BRANSTROM, Arthur, A.; NARASIMHAN, Jana; DUMBLE, Melissa, L.; HEDRICK, Jean; WEETALL, Maria, L.; (260 pag.)WO2016/25933; (2016); A2;,
Indoline – Wikipedia,
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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. 143262-20-8, name is 1-(tert-Butoxycarbonyl)indoline-7-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-(tert-Butoxycarbonyl)indoline-7-carboxylic acid

(1) 7-Indolinecarboxamide To a mixture of 1-(tert-butoxycarbonyl)-7-indolinecarboxylic acid (3.67 g, 13.9 mmol), chloroform (30 mL) and a drop of dimethyl formamide was added dropwise with stirring oxalyl chloride (5.5 mL, 63.0 mmol) over a period of 5 minutes at room temperature. After the addition, the reaction mixture was warmed to 60 C., and stirred at 60 C. for 2 hours. The reaction mixture was concentrated under reduced pressure, and thereto was added toluene (about 100 mL), and the mixture was further concentrated under reduced pressure. To the residue was added tetrahydrofuran (80 mL), and thereto was added with stirring a 29% aqueous ammonia (55 mL) with stirring under ice-cooling. The mixture was warmed to room temperature and stirred overnight. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with a saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel column chromatography (SiO2, hexane:ethyl acetate=1:2, and then ethyl acetate) to give 7-indolinecarboxamide (2.02 g, yield: 90%). 1H NMR (DMSO-d6) 67; 7.62 (br, 1H), 7.36 (d, 1H, J=8.1 Hz), 7.08 (d, 1H, J=7.0 Hz), 7.00 (br, 1H), 6.61 (s, 1H), 6.46-6.41 (m, 1H), 3.52 (t, 2H, J=8.5 Hz), 2.90 (t, 2H, J=8.5 Hz)

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 143262-20-8.

Reference:
Patent; Masumoto, Shuji; Kitano, Masahumi; Ohashi, Naohito; US2003/105118; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, 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 201940-08-1, Computed Properties of C13H16BrNO2

Example 3-91 a 2,3-Dihydro-1H-isoindole-5-carboxylic acid methyl ester was synthesised according to the following scheme: 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*25 mL). The organic layer was dried (Na2SO4), 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).

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 5-bromoisoindoline-2-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Blatt, Lawrence M.; Andrews, Steven W.; Condroski, Kevin R.; Doherty, George A.; Jiang, Yutong; Josey, John A.; Kennedy, April L.; Madduru, Machender R.; Stengel, Peter J.; Wenglowsky, Steven M.; Woodard, Benjamin T.; Woodard, Laura; US2005/267018; (2005); A1;,
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Synthetic Route of 6780-38-7,Some common heterocyclic compound, 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, molecular formula is C10H6ClNO3, 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.

271 g of water was put in a 1 L four-necked flask and cooled to 10 C. 7 7 g (570.4 mmol) of potassium carbonate was added thereto and dissolved. This was cooled to 3 C. and 30.1 g (223.2 mmol) of 2,2,2-trifluoroethylamine hydrochloride was added thereto. The solution was stirred at 3 C. for 10 minutes, and a solution of 50 g (223.2 mmol) of phthaloylglycyl chloride dissolved in 150.7 g of acetonitrile was added dropwise thereto at such a rate that the reaction solution kept at 20 C. or lower. After stirring for 1 hour, the product precipitated in the reaction was filtered and washed with 150.7 g of water. The obtained solid was dried under reduced pressure at 60 C. to obtain 2-phthaloyl-N- (2,2,2-trifluoroethyl) acetamide as a white solid. The yield was 59.7 g, and the yield was 93.5%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, its application will become more common.

Reference:
Patent; Nissan Chemical Industries, Ltd.; Moriyama, yuji; (16 pag.)JP5652628; (2015); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

201940-08-1, name is tert-Butyl 5-bromoisoindoline-2-carboxylate, 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. category: indolines-derivatives

To solution of the aryl bromide (0.200 g, 0.67 mmol) and Pd (PPh3) 4 (39 mg, 0.33 mmol) dissolved in THF under N2 was cannulated the crude vinyl zinc species from step A. The reaction was heated at 50C for 36 hours, and the then filtered through a plug of A1203 with aid of EtOAc and concentrated to give an oil which was used without further purification

The synthetic route of 201940-08-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA INC.; WO2005/37214; (2005); A2;,
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

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. 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