Tag: M.W=200-300

Related Products of 6941-75-9,Some common heterocyclic compound, 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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: Preparation of 5-BromoisoindoIine.To a solution of 5-bromoisoindoline-l,3-dione (8.117 g, 35.9 mmol) in THF (10 mL) was added boron trifluoride (8.40 mL, 108 mmol) dropwise. The reaction mixture was heated to reflux. After refluxing temperature was reached, borane tetrahydrofuran complex (144 mL, 144 mmol) was added dropwise and the reaction was stirred at reflux for 16 h. The mixture was cooled to 0 0C, cautiously treated with 3 N HCl (10 mL), and stirred at room temperature for 1 h. The aqueous mixture was washed with EtOAc, and the organic phase was discarded. The aqueous layer was basifed (pH 9-10) and extracted with EtOAc. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound (4.02 g). LCMS m/z = 198.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2009/105206; (2009); A1;,
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Electric Literature of 552330-86-6, A common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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 271: (S)- l-Oxo-N-((4-(trifluoromethyl)phenyl)(3-(trifluoromethyl)- pyridin-2-yl)methyl)isoindoline-5-carboxamide.Step 1. Methyl l-oxoisoindoline-5-carboxylate.To a 25 mL round bottom flask containing 5-bromo-2,3-dihydro-isoindol- 1-one (500 mg, 2.36 mmol), was added TEA. The resulting mixture was then stirred at 23 C for 2 min. At this time, MeOH (954 mu,, 23.58 mmol), 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (54.6 mg, 0.094 mmol)(Xantphos) and palladium(II) acetate (10.59 mg, 0.047 mmol) were added to the flask. The reaction mixture was then flushed with argon and then with carbon monoxide. The flask was fitted with a rubber septa and a balloon of carbon monoxide was inserted through septa. The flask was stirred at 70 C overnight under carbon monoxide, allowed to cool, diluted with EtOAc (50 mL) and filtered through Celite eluting with EtOAc (300 mL). The solid remaining on the Celite pad was washed with DCM (200 mL) and DCM/MeOH (10: 1)(150 mL) and the filtrates concentrated to give a pale green solid (800 mg). A portion of this material was taken on to the next reaction with no further purification.

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; AMGEN INC.; BISWAS, Kaustav; BROWN, James; CHEN, Jian, J.; GORE, Vijay, Keshav; HARRIED, Scott; HORNE, Daniel, B.; KALLER, Matthew, R.; LIU, Qingyian; MA, Vu, Van; MONENSCHEIN, Holger; NGUYEN, Thomas, T.; YUAN, Chester, Chenguang; ZHONG, Wenge; ST. JEAN, David, J., Jr.; WO2012/177893; (2012); A2;,
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Adding a certain compound to certain chemical reactions, such as: 1336963-95-1, name is 6-Bromo-7-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 1336963-95-1, Computed Properties of C8H3BrFNO2

In a solution of compound 2 (2.80 g, 11.48 mmol) in 50 ml of ethanol,Hydrazine hydrate (85%, 0.5 mL) was added under a nitrogen atmosphere,After refluxing for thirty minutes,There is a yellow product after precipitation by suction after drying,Was dissolved in 50 ml of ethanol,T-BuOK (4.03 g, 35.90 mmol) was added,After refluxing for 2 h, the reaction mixture was poured into water,The pH of the system was adjusted to 2 with hydrochloric acid,After extraction with ethyl acetate,Washed,Saturated salt water washing,After drying, distillation under reduced pressure.After the column by silica gelTo give the title compound 3 (1.49 g, yield 56%).

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; Peking University; Pei, Jian; Lei, Ting; Dou, Jinhu; (29 pag.)CN103804271; (2016); B;,
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Application of 169037-23-4, The chemical industry reduces the impact on the environment during synthesis 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, I believe this compound will play a more active role in future production and life.

To a solution of 5-trifluoromethoxyisatin (12A, 0.46g, 2.00mmol) in CH2Cl2 (15mL) was added mCPBA (70% pure, 0.54g, 2.2mmol). The resulting solution was allowed to stir for 30 minutes. A solid precipitate formed and was filtered, rinsed with CH2CI2, and dried to yield compound 12B as a solid (0.39g, 79%).

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-(Trifluoromethoxy)indoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; WO2009/143049; (2009); A1;,
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Synthetic Route of 181140-34-1, 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. 181140-34-1 name is (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, 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: Compounds 2-5 were synthesized using a modified procedure originally reported by Roehrig et al.28 To a cooled solution of (R)-(-)-N-(2,3-epoxypropyl)phthalimide 1 (102 mg, 0.50 mmol) in 10 mL of 2-propanol, amine or aminoalcohol (0.6 mmol, 1.2 equiv) in 10 mL of 2-propanol was added at 0 C and stirred for 1 h. It was then refluxed for 8 h. After the completion of the reaction, the solvent was removed under reduced pressure and the crude product was purified by flash chromatography on silica gel (CHCl3/MeOH 1:20 as eluent) to afford 2-5 as white crystals.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (R)-(-)-N-(2,3-Epoxypropyl)phthalimide, and friends who are interested can also refer to it.

Reference:
Article; Bozkurt, Selahattin; Durmaz, Mustafa; Naziroglu, Hayriye Nevin; Yilmaz, Mustafa; Sirit, Abdulkadir; Tetrahedron Asymmetry; vol. 22; 5; (2011); p. 541 – 549;,
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These common heterocyclic compound, 1029691-06-2, name is 2-(3-Oxocyclopentyl)isoindoline-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. HPLC of Formula: C13H11NO3

To a mixture of DIPEA (5.32 g, 41.17 mmol) and S4 (5.9 g, 25.73 mmol) in DCM (100 mL) was added Tf2O (8.7 g, 30.9 mmol) dropwise at 0 C. for 30 min. The reaction mixture was stirred at 0 C. for 16 hrs. After dilution with DCM, the mixture was washed with aq. NH4Cl solution and aq. NaHCO3solution successively. The organic phase was dried over anhydrous Na2SO4, filtered and concentrated to give crude product, which was purified by column chromatography on silica gel (eluted with petroleum ether: ethyl acetate=4:1) to give the title compound (6.3 g, 67.7% yield) as off-white solid.

The synthetic route of 2-(3-Oxocyclopentyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAK, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; (905 pag.)WO2017/35353; (2017); A1;,
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Related Products of 2436-29-5,Some common heterocyclic compound, 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, molecular formula is C11H9NO3, 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 mixture of (R)-(l-amino-but-3-ynyl)-7-chloro-3-phenylamino-3H-quinazolin-4-one (4.60 g, 12.2 mmol) and diisopropylethylamine (DIPEA) (5.5 ml) in dichloromethane (60 ml) was added a solution of 3-(l,3-dioxo-l,3-dihydro-isoindol-2-yl)-propionaldehyde (2.45 g, 12.1 mmol) in dichloroethane (10 ml), followed by a solution of sodium triacetoxy borohydride (NaBH(OAc)3) (0.25M in dichloroethane, 100 ml). The reaction mixture was stirred at room temperature and the reaction progress was monitored by HPLC/MS. Upon completion, a saturated sodium carbonate solution (100 ml) was added. The resulted organic layer was collected and washed with brine solution. The solvent was removed and residue was purified by flash column to afford 2- {3-[(R)- 1 -(7-chloro-4-oxo-3-phenylamino-3,4-dihydro-quinazolin-2-yl)-but-3- ynylamino]-propyl}-isoindole-l,3-dione (6.1 g, 95%) as off-white solid. M.p. 78-80 0C. LCMS: m/e 526 [M+H]. 1H NMR (DMSO-d6): delta 9.09 (s, br, IH), 8.07 (d, J= 8.8 Hz, IH), 7.74 (m, IH), 7.83-7.76 (m, 5H), 7.58 (dd, J= 8.8 and 2.0 Hz, IH), 7.17 (t, J= 7.6 Hz, 2H), 6.83 (brm, IH), 6.65 (m, 2H), 4.1 and 4.0 (s,s, br, IH, rotomers), 3.6 (t, J= 6.8Hz, 2H), 2.75 (s, br, 1 H), 2.67- 2.52 (brm, 2H), 2.35 (brm, 2H), 1.67 (brm, 2H).

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARQULE, INC.; WO2009/2808; (2008); A2;,
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Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, 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 118289-55-7, Recommanded Product: 6-Chloro-5-(2-chloroethyl)indolin-2-one

5-(2-(4-(1,2-benzisothiazol-3-yl)-piperazinyl)ethyl)-6-chloro-1,3-dihydro-2H-indol-2-one A clean and dry 20-gallon glass lined tank was charged with 19 L of water and 4.44 Kg of sodium carbonate, after the carbonate had dissolved 4.29 Kg (17.5 moles) of 5-(2-chloroethyl)-6-chloro-oxindole and 3.62 Kg (1 6.5 moles) of 1-(1,2-benzisothiazol-3-yl) piperazine were added. The aqueous slurry was heated to reflux and the temperature maintained for 14 hours. When the reaction was complete the solution was cooled to 20 C. and filtered. The wet product was reslurried in 23 L of isopropyl alcohol at room temperature for 2 hours. The product was collected by filtration on 2 large Buchner funnels, each was washed with 3.4 L of fresh isopropyl alcohol. The product was vacuum dried at 30 to 40 C. until no isopropyl alcohol remained, giving 5.89 Kg (86.4% yield) of the desired free base which matched a standard sample by high performance liquid chromatography (HPLC).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Chloro-5-(2-chloroethyl)indolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; Pfizer Inc.; US5312925; (1994); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 132898-96-5,Some common heterocyclic compound, 132898-96-5, name is 2,3-Dioxoindoline-5-sulfonyl chloride, molecular formula is C8H4ClNO4S, 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 1: N-Benzyl-N-methyl-2,3-dioxoindoline-5-sulfonamide To a black solution of 2,3-Dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride (4.00 g, 16.3 mmol) in 1:1 THF:CHCl3 was added, drop-wise via syringe pump, a solution of N-benzylmethylamine (2.73 mL, 21.2 mmol, 1.3 eq) and N,N-diisopropylethylamine (5.68 mL, 32.6 mmol, 2 eq) in CHCl3 (32 mL) over a period of 1.25 hr. with cooling in an ice bath. After stirring for 50 min. the reaction was allowed to warm to room temperature and stirred for 30 minutes. The reaction was concentrated. The crude product was purified on Biotage KP silica gel eluding with 98/2 CHCl2/CH3OH to give the analytically pure sample of the title compound as a bright yellow solid (0.18 g, 15% yield). Anal. Calc’d for C16H14N2O4S: C, 58.17; H, 4.27; N, 8.48; Found: C, 57.88; H, 4.36; N, 8.40; MS: (API-ES-) m/z 329 [M-H]. m.p.: 183-185 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Dioxoindoline-5-sulfonyl chloride, its application will become more common.

Reference:
Patent; Wyeth; US2005/250798; (2005); A1;,
Indoline – Wikipedia,
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3339-73-9, name is 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid, 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. Application In Synthesis of 3-(1,3-Dioxoisoindolin-2-yl)propanoic acid

A mixture of phthalic anhydride and beta-alanine were heated to 190-200C in a sealed tube. Stirred for additional 30min at 190-200C after the solids totally melted. The reaction mixture was cooled to room temperature and 50% EtOH/water was added. The resulted suspension was filtered and the white precipitate was further washed with 50% EtOH/water, and then dried under vacuum overnight to give the N- phthaloyl-beta-alanine. Phosphoryl chloride was added to a suspension of N-phthaloyl- beta-alanine and phenylethylamine in acetionitrile. The suspension was stirred for 6h under reflux. Acetonitrile and phosphoryl chloride was removed by vacuum. The reaction mixture was then diluted with DCM and washed with sat NaHCC>3 solution, water and brine, then dried over anhydrous Na2S04. The filtrate was concentrated and the residue was purified by column chromatography using acetonitrile (0 to 20 %) in DCM as eluent to afford the imine compound. Acetic acid and sodium triacetoxyborohydride were added to a solution of imine compound in DCM and stirred for lh at room temperature. The reaction mixture was then washed with sat NaHCC>3 solution, water and brine, then dried over anhydrous Na2S04. The filtration was concentrated and the residue was purified by column chromatography using acetonitrile (0 to 50%) in DCM as eluent to give the amine compound. Cis-l ,2-Cyclohexanedicarboxylic anhydride was added to a solution of amine compound in p-xylene at 50C and stirred for 3h. The reaction mixture was concentrated under vacuum and the residue was purified by column chromatography using acetonitrile (0 to 20% with 1% AcOH) in DCM as eluent to give the designed product. Two diastereomers were separated by HPLC using water plus 0.1 %TFA and acetonitrile plus 0.1 %TFA as solvents.

The synthetic route of 3339-73-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; THE BROAD INSTITUTE, INC.; HU, Longqin; MAGESH, Sadagopan; CHEN, Lin; LEWIS, Timothy; MUNOZ, Ben; WANG, Lili; WO2013/67036; (2013); A1;,
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