Tag: M.W=200-300

Reference of 675109-26-9, These common heterocyclic compound, 675109-26-9, name is 6-Bromoisoindolin-1-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.

A mixture of 6-bromoisoindolin-1-one (287 mg, 1.35 mmol), 1-methyl-5-(tributylstannyl)-1H-imidazole (500 mg, 1.35 mmol), Pd(dppf)Cl2 (33 mg, 0.041 mmol) and Cs2CO3 (1.32 g, 4.05 mmol) in dioxane (50 mL) and water (8 mL) was heated to 100 C. overnight. After cooling, the mixture was concentrated under vacuum and purified by column chromatography on silica gel ((1%-3% MeOH in DCM) to afford 9A (220 mg, 76% yield) as a brown solid: 1H NMR (400 MHz, DMSO-d6) delta 8.66 (s, 1H), 7.76-7.15 (m, 4H), 7.15 (s, 1H), 4.43 (s, 2H), 3.72 (s, 3H); ESI m/z 214.1 [M+1]+.

Statistics shows that 6-Bromoisoindolin-1-one is playing an increasingly important role. we look forward to future research findings about 675109-26-9.

Reference:
Patent; Seal Rock Therapeutics, Inc.; BROWN, Samuel David; US2018/291002; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 954-81-4,Some common heterocyclic compound, 954-81-4, name is N-(5-Bromopentyl)phthalimide, molecular formula is C13H14BrNO2, 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 N-(5-bromopentyl)phthalimide (1.49 g, 5 mmol) and N,N-diisopropylethylamine (870 muL, 5 mmol) was dissolved in NMP (2 mL) followed by morpholine (870 muL, 5.5 mmol). The reaction mixture was stirred at room temperature overnight, the formed precipitate was filtered, and the filtrate evaporated. The crude product was triturated from EtOAc, filtered, and dried in vacuo to provide the alkylated morpholine intermediate (939 mg) as a white solid. The intermediate was dissolved in ethanol (20 mL) then treated with hydrazine hydrate (155 muL, 3.1 mmol). The reaction mixture was heated at reflux for 2 h, cooled to room temperature, and the formed precipitate was filtered. The filtrate was concentrated in vacuo, and the resulting residue was dissolved in chloroform (5 mL) followed by treatment with N-(9-fluorenylmethoxycarbonyl)-isothiocyanate (872 mg, 3.1 mmol) The reaction mixture was maintained at room temperature for 2 h, then concentrated in vacuo. The resulting oil was dissolved in EtOAc (5 mL), treated with piperidine (614 muL, 6.2 mmol), stirred at room temperature for 30 min, and concentrated in vacuo. The resulting residue was dissolved in dichloromethane (10 mL), and the formed precipitate was filtered and dried in vacuo to provide 1-(5-morpholinopentyl)thiourea (287 mg, 58%) as a yellowish amorphous solid.

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

Reference:
Patent; Dickson, John K.; Hodge, Carl Nicholas; Mendoza, Jose Serafin; Chen, Ke; US2006/52416; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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 1.02 g (7.4 mmol) of freshly calcined K2CO3, 7.0 mmol of the corresponding 2-thiouracil 1-3 and 7.7 mmol of 2-(bromomethyl)-2Hisoindole-1,3-dione in 20 mL of anhydrous DMF was stirred at room temperature for 72 h. The mixture was filtered, the fi ltrate was evaporated to dryness under reduced pressure. The precipitate of mineral salts on the filter was dissolved in 1 M. aqueous H3PO4 and the resulting solution was combined with the bottom residue. The resulting mixture was filtered. The filtercake was washed with water, and then the filtrate was extracted EtOAc (3¡Á50 mL). The filter cake was air dried to constant weight, and the organic extract was dried over anhydrous MgSO4. The dried organic extract was evaporated to dryness under reduced pressure. The residue was mixed with the filter cake and evaporated in a mixture with toluene (3¡Á50 mL) under reduced pressure. A crude product was obtained in the residue, which was subjected to further purification using preparative HPLC. 2-{[(6-Methyl-4-oxo-1,2-dihydropyrimidin-2-yl)-sulfanyl]methyl}-2H-isoindole-1,3-dione (4). Yield 63%, mp 251.5252.1C, Rf 0.38 (EtOAc – hexane, 2 : 1). IR spectrum (mineral oil), nu, cm-1: 3006, 1778, 1719,1574, 1540, 1464, 1292, 708. 1H NMR spectrum (400 MHz), delta, ppm: 2.07 s (3H, 3), 5.42 s (2, S2),6.06 s (1, ), 7.86-7.93 m (4Ar), 12.44 s (1, N).Mass spectrum, m/z (I, %): 302.3 (100) [M + H]+. Found,%: C 56.01; H 3.72; N 14.08; S 10.51. C14H11N3O3S.Calculated, %: C 55.80; H 3.68; N 13.95; S 10.64.

The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Babushkin, A. S.; Chapurkin, V. V.; Maryshev, A. Yu.; Navrotskii, M. B.; Novakov, I. A.; Ruchko, E. A.; Schols, D.; Sheikin, D. S.; Russian Journal of General Chemistry; vol. 90; 3; (2020); p. 352 – 356; Zh. Obshch. Khim.; vol. 90; 3; (2020); p. 365 – 370,6;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products 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.

General procedure: To a precooled stirring suspension of NaH (6.0 mmol, 0.144 g) in THF (10 mL) at -78 C was added a solution of N-methyloxindole (5a) (6.0 mmol, 0.883 g) in THF (10 mL) dropwise. Then the cooling bath was removed and stirring continued for 5 min (till the formation of clear solution). Then the reaction mixture was again cooled to -78 C and a solution of methyl 3-hydroxy-2-methylene-3-phenylpropanoate (6a) (2.0 mmol, 0.468 g) in THF (15 mL) was added dropwise over 30 min. After stirring for further 10 min at the same temperature, the cooling bath was removed and the reaction was quenched with saturated NH4Cl solution and extracted with EtOAc (3¡Á30 mL). Combined organic layer was dried over anhydrous Na2SO4.. Solvent was removed and the crude obtained was purified by column chromatography(10-15% EtOAc in hexanes) provided title compound (7a) (0.539 g) as a colorless solid in 84% yield.

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; Basavaiah, Deevi; Lingam, Harathi; Babu, Thelagathoti Hari; Tetrahedron; vol. 74; 19; (2018); p. 2306 – 2313;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 201940-08-1, 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. 201940-08-1 name is tert-Butyl 5-bromoisoindoline-2-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.

Commercially available tert-butyl 5-bromoisoindoline-2-carboxylate (i.e., Matric Scientific, catalog 74109) (20 g, 0.0671 mol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2- dioxaborolane) (17 g, 0.0671 mol), KAc (8.5 g, 0.087 mol) and PdCfedppf (1.8 g, 0.00221 mol) in 200 mL 1,4-dioxane was heated to 80C overnight. The mixture was cooled, water was added, the mixture was extacted with EA, dried and concentrated. The residue was purified by chromatography on silica gel to afford the title compound. 1HNMR (300MHz,DMSO)5: 1.2-1.3 (s, 12H), 1.4-1.5 (s, 9H), 4.5-4.6 (s, 4H), 7.2-7.3(m,lH), 7.5-7.6 (M,2H); LC-MS: m/z=246 (M+l-100)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 5-bromoisoindoline-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MANDAL, Mihir; TANG, Haifeng; XIAO, Li; SU, Jing; LI, Guoqing; YANG, Shu-Wei; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; HICKS, Jacqueline; LOMBARDO, Matthew; CHU, Hong; HAGMANN, William; PASTERNAK, Alex; GU, Xin; JIANG, Jinlong; DONG, Shuzhi; DING, Fa-Xiang; LONDON, Clare; BISWAS, Dipshikha; YOUNG, Katherine; HUNTER, David, N.; ZHAO, Zhiqiang; YANG, Dexi; WO2015/112441; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 5332-26-3, A common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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.

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

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:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 3339-73-9, 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 3339-73-9 as follows.

General procedure: 1.0 mmol of (1,3-dioxoisoindolin-2-yl) acid, N-ethyl-N-dimethylaminopropylcarbodiimide (EDC) (1.1 mmol), hydroxybenzotriazole(HOBt) (1.2 mmol) and N,N-Diisopropylethylamine (2.0 mmol) weremixed in minimum DMF and the obtained mixture was stirred for5 min. Then, 4-aminoquinoline-diamines (1.0 mmol) was added to thereaction mixture and the stirring was continued for 5 h. The reactionend was proved by thin layer chromatography (TLC). Then, DMF wasevaporated using rotary evaporator and cold water (20 mL) was added,and solid precipitates obtained were filtered and washed with coldwater. The crude product was recrystallized in absolute ethanol.

According to the analysis of related databases, 3339-73-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rani, Anu; Legac, Jenny; Rosenthal, Philip J.; Kumar, Vipan; Bioorganic Chemistry; vol. 88; (2019);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

6941-75-9, name is 5-Bromoisoindoline-1,3-dione, 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. SDS of cas: 6941-75-9

Synthesis of 5-bromo-3-hydroxy-3-(thiophen-3-yl) isoindolin-1-one (3) A solution of 1, 2-dibromoethane (20 ml, 230.35 mmol) in ether/benzene (270 ml/100 ml) was added to a stirred suspension of magnesium turning (8.64 g, 355.6 mmol) in ether (100 ml). The reaction was stirred at room temperature for 2 h. To this was added a solution of n-butyllithium (110 ml, 177.6 mmol) and 3-bromothiophene (2, 29 g, 177.6 mmol) in tetrahydrofuran (200 ml) (prepared at -78 C.) and the reaction was stirred at room temperature for 1 h. Then a solution of 4-bromophthalimide (1, 4 g, 17.7 mmol) in dichloromethane (50 ml) was added and the reaction was stirred at room temperature for 1 h. Progress of the reaction was monitored by TLC. After completion, the reaction mixture was quenched with sat. ammonium chloride and extracted with dichloromethane. The organic layer was separated, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified on combiflash using 25% ethyl acetate in hexane to afford mixture of 5-bromo-3-hydroxy-3-(thiophen-3-yl) isoindolin-1-one (3) as a yellow solid. Yield: 0.97 g, crude; MS (ESI) m/z 307.95 [M-1]-.

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; eFFECTOR Therapeutics, Inc.; Sprengeler, Paul A.; Reich, Siegfried H.; Ernst, Justin T.; Webber, Stephen E.; Shaghafi, Mike; Murphy, Douglas; Tran, Chinh; (131 pag.)US10112955; (2018); B2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 5332-26-3, These common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)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.

General procedure: The vacuum dried intermediate 3 (0.002 mol) was then reacted with mono- and di-substituted benzoic acids (0.003 mol) separately in presence of anhydrous potassium carbonate (0.003 mol) in DMF (10 mL). The reaction mixture was stirred at room temperature for about 2 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was poured into ice-cold water and allowed stir for 10 min. The solid obtained was filtered and washed successively with distilled water and recrystallized from ethanol to obtain4(a-n).

Statistics shows that 2-(Bromomethyl)isoindoline-1,3-dione is playing an increasingly important role. we look forward to future research findings about 5332-26-3.

Reference:
Article; Kumar, C.S. Chidan; Loh, Wan-Sin; Chandraju, Siddegowda; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong-Kun; PLoS ONE; vol. 10; 3; (2015);,
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., Formula: C11H9NO3

A mixture of 2,3-dihydro-1H-inden-2-amine (5.0 g, 24.61 mmol) and (R)-2-(oxiran-2-ylmethyl)isoindoline-1,3-dione (4.91 g, 36.91 mmol) in EtOH (100 mL) was heated at reflux overnight. After cooling to room temperature, triethylamine (9.94 g, 98.44 mmol) and (Boc)2O(10.74 g, 49.22 mmol) were added and the reaction mixture was stirred at room temperature overnight. The mixture was concentrated and purified by column (EtOAc / petroleum ether = 1/4, v/v) to give the title compound (5.4 g, 50%) as an oil.

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; CTxT PTY LIMITED; STUPPLE, Paul Anthony; (66 pag.)WO2017/153521; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem