Author: Jessica.F

Electric Literature of 924304-73-4, 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. 924304-73-4 name is 4-Chloroisoindoline hydrochloride, 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 4: Synthesis of (3J?,5S)-1-((S)-4-(but-3-enyIoxy)-2-(tert- butoxycarbonylamino)butanoyl)-5-((li?,25)-1-(ethoxycarbonyl)-2- vinylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chIoroisoindoline-2-carboxylate[0489] (17?,25)-ethyl l-((25,4i)-1-((5)-4-(but-enyloxy)-2-(tert- butoxycarboalphaylamino)butanoyl)-4-hydroxypyrrolidine-2-carboxamido)-2- vinylcyclopropanecarboxylate (0.55 g, 1.1 mmol) in THF (20 mL) was added 1,1 ‘- carbonyldiimidazole (0.204 g, 1.26 mmol) in one portion. The reaction was stirred at room temperature for 3 hours. To the reaction was then added the N-ethyl-N-isopropylpropan-2- amine (0.92 mL, 5.3 mmol), followed by 4-chloroisoindoline hydrochloride (0.258 g, 1.37 mmo.). The reaction was stirred at 50 C for 18 hours. The solvent was removed. The residue was partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. After removal of solvent, the residue was purified by chromatography (HexanerEthyl acetate=l :3) to give (3i?,5£)-1-((S)-4- (but-3-enyloxy)-2-(tert-butoxycarbonylamino)butanoyi)-5-(( IR,2S)- 1 -(ethoxycarbonyl)-2- vinylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chloroisoindoline-2-carboxylate as white solid (0.49 g, 66%). MS: Calcd.: 702.3; Found: [M+H]+ 703.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloroisoindoline hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; INTERMUNE, INC.; ARRAY BIOPHARMA, INC.; WO2008/137779; (2008); 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. 32692-19-6, name is 5-Nitroindoline, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Nitroindoline

General procedure: We described the synthesis of the compound 1 (Table 2) to illustrate the general procedure for TFA accelerated Petasis three-component reaction. The descriptions of the preparations of all reported compounds are in the Supporting information section. To a magnetically stirred mixture of 5-nitroindoline (0.164 g, 1.0 mmol), 4-tolyboronic acid (0.135 g, 1.0 mmol), and glyoxylic acid monohydrate (0.092 g, 1.0 mmol) in CH2Cl2 (5 ml) was added TFA (20 mul). The mixture was stirred at room temperature for 4 h. After the completion of the reaction (TLC monitoring), half of the solvent was evaporated by means of a rotovap. The resulting solid was filtered through a sintered glass funnel. The collected solid was thoroughly washed with petroleum ether and a small amount of ice water (5 ml), and then dried in vacuo at room temperature for 24 h to afford 0.26 g (83.3 %) of 2-(5-nitroindolin-1-yl)-2-(p-tolyl) acetic acid as a light 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:
Article; Zhang, Jing; Yun, Fan; Xie, Rui; Cheng, Chunhui; Chen, Guangyao; Li, Jingxuan; Tang, Pingwah; Yuan, Qipeng; Tetrahedron Letters; vol. 57; 35; (2016); p. 3916 – 3919;,
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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. 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, A new synthetic method of this compound is introduced below., SDS of cas: 3891-07-4

Preparation of Ethyl 4-[2-(PHTHALIMIDO) ETHOXY] ACEFOACETATE (X1 A 250 mL two-necked flask, equipped with a magnetic stirring bar, thermometer and a pressure equalized addition funnel was charged with 75 mL of tetrahydrofuran under nitrogen atmosphere. 7.53 g Sodium hydride (60% dispersed in oil) was added and the resulting suspension was cooled to-10 C and 20 g of N- (2-HYDROXYETHYL) PHTHALIMIDE was added slowly over 5 minutes. The resulting slurry was stirred at-10 C for 30 minutes. To this mixture a solution of 16.35 g ethyl 4-chloroacetoacetate in 30 ML of TETRAHYDRAFURAN was added at-10 C in 40 minutes. The reaction mixture was warmed to room temperature and then stirred at room temperature for 18 hours. The reaction mixture was placed in an ice bath and quenched by dropwise addition of 10 mL ethanol. The mixture was then poured into 150 mL of IN hydrochloric acid solution in crushed ice and 200 ML of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 70 mL of ethyl acetate was added. The resulting mixture was transferred into a separatory funnel and the aqueous phase was separated. The organic phase was first washed with 70 mL of 5 wt. % OF NAHC03 solution, then with 150 ML of water, dried over 5 G of MgS04. MgS04 was filtered off and the filtrate was concentrated in vacuo to give a light brown oily product. The oil was washed with 15 mL of hexane to remove the mineral oil to give 17.2 g of ethyl 4- [2- (phthalimido) ethoxy] acetoacetate light brown product. (yield 51%, rel. compound purity > 80%). IR (KBR, CM~L) : 2995 and 1716. 1H-NMR (CDC13) 6 7.76 (dd, 2H), 7.65 (dd, 2H), 4.11 (S, 2H), 4.02 (q, 2H), 3.80 (t, 2H), 3.70 (t, 2H), 3.37 (s, 2H), 1. 16 (t, 3H). 13C-NMR (CDC13) 8 201.7, 168.4, 167.2, 134.3, 132.2, 123.5, 75.6, 68.7, 61.6, 46.0, 37.4, 14.3.

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; EOS ECZACIBASI OZGUN KIMYASAL URUNLER SANAYI VE TICARET A.S.; WO2004/58711; (2004); A1;,
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Synthetic Route of 3485-84-5, These common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, 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: In a sealed tube under argon atmosphere, were introducedcompound 4 (4.74 g, 20 mmol), DMF (20 mL), triethylamine(11.16 mL, 80 mmol), palladium diacetate (225 mg, 1 mmol), tri(otolyl)-phosphine (609 mg, 2 mmol) and N-vinylphthalimide (5.20 g,30 mmol). The mixturewas stirred at 110 C for 3 h and hydrolyzed.The formed solid was solubilized in CH2Cl2, washed with water andbrine, dried over MgSO4 and evaporated under reduced pressure.The crude productwas recrystallized from acetonitrile to afford 7 asa white solid (91% yield)

Statistics shows that N-Vinylphthalimide is playing an increasingly important role. we look forward to future research findings about 3485-84-5.

Reference:
Article; Landagaray, Elodie; Ettaoussi, Mohamed; Rami, Marouan; Boutin, Jean A.; Caignard, Daniel-Henri; Delagrange, Philippe; Melnyk, Patricia; Berthelot, Pascal; Yous, Said; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 621 – 631;,
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Synthetic Route of 1168150-46-6, These common heterocyclic compound, 1168150-46-6, name is (E)-Methyl 3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate, 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: A mixture of intermediate (3a, 3b, 6a, 6b, 10a, 10b, 11a-d, and14a-g, 1.5 mmol) and methyl (E)-3-(methoxy(phenyl)methylene)-2-oxoindoline-6-carboxylate (1.5 mmol) in methanol (10 mL) wasstirred under reflux for 5-10 h. When TLC showed the completionof the reaction, the solution was cooled to room temperature. Theprecipitate was filtered off to give a crude product, which wasrecrystallized from methanol to provide the target compounds.

The synthetic route of 1168150-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Mingze; Tian, Ye; Sun, Xiaoqing; Yu, Simiao; Xia, Juanjuan; Gong, Ping; Zhang, Haotian; Zhao, Yanfang; European Journal of Medicinal Chemistry; vol. 139; (2017); p. 492 – 502;,
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Synthetic Route of 480-91-1,Some common heterocyclic compound, 480-91-1, name is Isoindolin-1-one, molecular formula is C8H7NO, 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.

Sodium hydride 60% in mineral oil (0.750 mg, 30.0 mmol) and dry THF (150 ml) were added to a two-necked round-bottomed flask. Isoindolin-1-one (5) (2.50 g, 18.8 mmol) was added to the suspension at 0 C under N2. The reaction mixture wasstirred for 30 min at 0 C, and then potassium bromomethyl trifluoroborate (3.00 g, 15.0 mmol) was added to the reaction mixture in one portion and stirred for 30 min at 0 C. The reaction mixture was warmed to room temperature and refluxed for 48 h. The reaction mixture was cooled to 0 C and quenched by KHF2 (3.0 M) in H2O (14 mL). The reaction mixture was stirred at room temperature for 2 h. The solvents were removed under vacuum, and residue was dissolved in ethyl acetate (100 mL) and filtered. The solid obtained was triturated with boiling acetone (3 x 50 mL) and the resulting white powder was washed with cold ether (3 x 20 mL) and dried to give the potassium N-methyltrifluoroborate isoindolin-1-one (6) as white solid (2.54 g, 65%): mp: 229-234 C; IR (KBr, neat): 3032, 2936, 2897, 2879, 1658, 1590, 1473, 1455, 1426, 1415, 1306, 1228, 1210, 1099, 1069, 1011, 996, 760, 726, 538 cm-1; 1H NMR (DMSO-d6, 400 MHz) delta = 7.59 (d, J = 8.0 Hz, 1H), 7.53-7.46 (m, 2H), 7.42-7.39 (m, 1H), 4.38 (s, 2H), 2.47 (s, 2H); 13C NMR (DMSO-d6, 100 MHz) delta = 169.9, 144.0, 131.5, 131.2, 127.5, 123.7, 122.7, 44.8; 11B NMR (DMSO-d6, 128.37 MHz) delta = 3.46 (br s); 19F NMR (DMSO-d6, 376.49 MHz): delta = 138.67. HRMS (ESI-TOF) m/z calcd. for C9H8BNOF3 (M-K) 214.0651; found 214.0661.

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

Reference:
Article; Nadaf, Rashid N.; Seapy, Dave G.; Synthetic Communications; vol. 44; 14; (2014); p. 2012 – 2020;,
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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. 552330-86-6, name is 5-Bromoisoindolin-1-one, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromoisoindolin-1-one

Step 1: Methyl 3-((1-oxoisoindolin-5-yl)thio)propanoate (0451) (0452) A solution of 5-bromoisoindolin-1-one (10 g, 47.16 mmol) in dioxane (450 mL) was degassed before Xantphos (2.73 g, 4.72 mmol), DIPEA (9.88 mL, 56.59 mmol), Pd2(dba)3 (2.159 g, 2.36 mmol) and methyl 3-mercaptopropanoate (32.6 mL, 330.12 mmol) was added. The reaction was heated to 80 C. for 1 h. The reaction was concentrated in vacuo. Approximately half of the material was purified by flash chromatography eluting with 0-5% methanol in EtOAc to afford 4.69 g of product. Only half the material was purified this way because the crude material solidified part way through loading onto the column. The solidified material was triturated with methanol and 4.48 g of product was collected by filtration as a colorless solid. The mother liquor was concentrated in vacuo and purified by flash chromatography eluting with 0-5% methanol in EtOAc to afford 1.1 g product. This was combined with the material from the first column to give 10.27 g (86%) of the title compound. (0453) LC/MS: m/z=252 [M+H]+. 1H NMR (500 MHz, DMSO) delta 2.69 (t, 2H), 3.26 (t, 2H), 3.60 (s, 3H), 4.34 (s, 2H), 7.38 (d, 1H), 7.52 (s, 1H), 7.58 (d, 1H), 8.48 (s, 1H).

According to the analysis of related databases, 552330-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AstraZeneca AB; NARJES, Frank; OLSSON, Roine Ingemar; VON BERG, Stefan; LEVER, Sarah; (112 pag.)US2017/166527; (2017); A1;,
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Reference of 3485-84-5, A common heterocyclic compound, 3485-84-5, name is N-Vinylphthalimide, molecular formula is C10H7NO2, 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 20-mL, microwave reaction vessel was charged with (4-bromopyridin-3-yl)-(4-(trifluoro methyl)phenyl)methanol (0.87 g, 2.62 mmol), 2-vinylisoindoline-1,3-dione (499 mg, 2.88 mmol), Pd(dba)2 (75.3 g, 0.13 mmol), 2-(dicyclohexyl-phosphino)biphenyl (91.8 mg, 0.26 mmol), NEt3 (0.44 ml, 3.14 mmol), and DMF (2 mL). The mixture was purged with argon and heated in microwave synthesizer at 150 C. for 1 h. The reaction mixture was partitioned between water and EtOAc. The EtOAc layer was separated and aqueous layer was extracted again with EtOAc. The combined organic layers were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (0-10% MeOH in DCM) to give the mixture (0.4 g) of (E)-2-(2-(3-(hydroxy(4-(trifluoromethyl)phenyl)methyl)pyridin-4-yl)-vinyl) isoindoline-1,3-dione and 2-(2-(3-(hydroxy(4-(trifluoromethyl)phenyl)-methyl)pyridin-4-yl)ethyl)isoindoline-1,3-dione as a light yellow semi-solid. MS (ESI pos. ion) m/z: 425 and 427.

The synthetic route of 3485-84-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nishimura, Nobuko; Norman, Mark H.; Tamayo, Nuria; Tang, Phi; Bo, Yunxin Y.; US2009/82358; (2009); A1;,
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Related Products of 20870-79-5, 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. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Appel?s salt (Scheme 2, 1; 4,5-dichloro-1,2,3-dithiazolium chloride; 15.76 mmol) was added to asolution of each appropriate 2-oxindole derivative (Scheme 2, 2a-d; 14.33 mmol) in CH2Cl2 (20 mL).After a few minutes, the uncolored mixture turned to a dark red color, and was stirred at roomtemperature for 18 h. The solvent was evaporated under reduced pressure, and the crude productwas dissolved with acetone (a minimum of 30 mL), and then precipitated with water (300 mL).The heterogeneous mixture was filtered in a vacuum, and the red solid was washed three times withwater (25 mL). This solid was finally dried over phosphorus pentoxide in a vacuum in a desiccator.

The chemical industry reduces the impact on the environment during synthesis 5-Nitroindolin-2-one. I believe this compound will play a more active role in future production and life.

Reference:
Article; Letribot, Boris; Delatouche, Regis; Rouillard, Herve; Bonnet, Antoine; Cherouvrier, Jean-Rene; Domon, Lisianne; Besson, Thierry; Thiery, Valerie; Molecules; vol. 23; 6; (2018);,
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These common heterocyclic compound, 18711-13-2, name is 4,7-Dichloroindoline-2,3-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: C8H3Cl2NO2

General procedure: A mixture of 1 (0.4 mmol), 2 (0.4 mmol), Na2CO3 (0.8 mmol) and TBHP (0.4 mmol) in DMF (4 mL) was stirred at rt for 2 h. Then, the mixture was poured into ice-water, acidified with 1 N HCl aq. (6 mL). The mixture was extracted with ethyl acetate (20 mL x 3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give desired products..

The synthetic route of 4,7-Dichloroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Jun; Zhang, Hui; Ding, Xiao; Tan, Xuefei; Shen, Hong C.; Chen, Jie; He, Weimin; Deng, Hongmei; Song, Liping; Cao, Weiguo; Journal of Fluorine Chemistry; vol. 220; (2019); p. 54 – 60;,
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