Tag: M.W=200-300

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 337536-15-9 as follows. SDS of cas: 337536-15-9

EXAMPLE 854-(6-Amino-5-((R)-1-(5-fluoro-2-(2H-1 ,2,3-triazol-2-yl)phenyl)ethoxy)pyridin-3- yl)isoindolin-1-oneA mixture of preparation 45 (100 mg, 0.264 mmol), 4,4,5,5,4′,4,,5′,5,-Octamethyl- [2,2′]bi[[1 ,3,2]dioxaborolanyl] (1 14 mg, 1.7 eq), and potassium acetate (90.7 mg, 3.5 eq) in DMSO (1.0 mL) was deoxygenated with N2 bubbler for 30 minutes before addition of the Pd(dppf)CI2 (9.5 mg, 0.05 eq). The mixture was then heated in 80C oil bath for 3 hr. LCMS indicated disappearance of starting bromide. To the crude boronate mixture was added 4-bromoisoindolin-1-one (84 mg, 1.5 eq), CsF (120 mg, 3.5 eq) and MeOH (2 ml_). The mixture was thoroughly degassed and Pd(dppf)Cl2 (9.5 mg, 0.05 eq) was added. The mixture was heated in the microwave at 120 C for 1 hr. LCMS showed the desired product mass. Mixture was filtered and purified with a reverse phasepreparative HPLC under acidic condition to give the title compound as an amorphous white solid (57.8 mg, 50.9%).1H NMR (600 MHz, DMSO-d6) delta ppm 1.59 (d, J=6.14 Hz, 3 H), 4.07 – 4.21 (m, 1 H), 4.23 – 4.34 (m, 1 H), 5.56 (q, J=6.06 Hz, 1 H), 6.19 (s, 2 H), 6.77 (s, 1 H), 7.34 (td, J=8.26, 2.94 Hz, 1 H), 7.41 (d, J=7.42 Hz, 1 H), 7.51 (t, J=7.55 Hz, 1 H), 7.57 (s, 1 H), 7.63 – 7.67 (m, 1 H), 7.70 – 7.72 (m, 1 H), 7.72 (d, J=1.28 Hz, 2 H), 8.20 (s, 1 H), 8.64 (s, 1 H).

According to the analysis of related databases, 337536-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
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Electric Literature of 552330-86-6, These common heterocyclic compound, 552330-86-6, name is 5-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.

To a solution of 5-bromo-2,3-dihydro-isoindol-1-one (200.00 mg; 0.90 mmol; 1.00 eqf.) in anhydrous 1 ,4-dioxane (4.00 mL), bis(pinacolato)diboron (255.40 mg; 0.99 mmol; 1.10 eqf.), KOAc (307.79 mg; 3.14 mmol; 3.50 eqf.) and dppf (49.68 mg; 0.09 mmol; 0.10 eqr.) are added. RM is purged with argon and Pd(dppf)CI2 (65.54 mg; 0.09 mmol; 0.10 eqf.) is added. RM is stirred at 1 10C for 16 h. RM is filtered through a pad of Celite and partitioned between EtOAc and water. The aqueous phase is washed with EtOAc, combined organic layers are washed with brine, dried over Na2S04 and concentrated in vacuo to afford 5-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-2,3-dihydro- isoindol-1-one (377.00 mg; 68 %; 42 % by UPLC) as a brown powder. Crude product is used for futher reactions.

The synthetic route of 552330-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SELVITA S.A.; FABRITIUS, Charles-Henry Robert Yves; NOWAK, Mateusz Oktawian; WIKLIK, Katarzyna Anna; SABINIARZ, Aleksandra Barbara; BIE?, Marcin Dominik; BUDA, Anna Ma?gorzata; GUZIK, Pawel Szczepan; JAKUBIEC, Krzysztof Roman; MACIUSZEK, Monika; KWIECI?SKA, Katarzyna; TOMCZYK, Mateusz Micha?; GA??ZOWSKI, Micha? Miko?aj; GONDELA, Andrzej; DUDEK, ?ukasz Piotr; (681 pag.)WO2016/180536; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 954-81-4, name is N-(5-Bromopentyl)phthalimide, 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 954-81-4, Recommanded Product: N-(5-Bromopentyl)phthalimide

Under a protective nitrogen atmosphere, sodium hydride (NaH, 48 mg, 1.2 mmol) is added into a solution of berbamine dihydrochloride (205 mg, 0.3 mmol) in N,N-dimethyl formamide (5 ml) at 0 C., after being stirred for 1 hour, 2-(5-bromoamyl)-isoindoline-1,3-dione (133 mg, 0.45 mmol) is added therein. The reaction solution is heated to 80 C. overnight. Then the reaction mixture is evaporated under vacuum, and purified by a preparative thin layer chromatography to give white or pale yellow compound (BS-BE-002) (98.4 mg, 39.8%). [0109] LC/MS m/z: M+1 824.2 100% (purity). 1H NMR (CDCl3) delta:7.8267.809 (dd, 2H, J=5.5 Hz, 5.5 Hz), 7.6927.680 (dd, 2H, J=6.0 Hz, 5.5 Hz), 7.267.243 (m, 2H), 7.0847.071 (d, 1H, J=6.5 Hz), 6.796.733 (m, 2H), 6.6236.607 (d, 1H, J=8.0 Hz), 6.529 (s, 1H), 6.395 (s, 1H), 6.272 (s, 1H), 5.971 (s, 1H), 4.0694.042 (t, 2H, J=6.5 Hz, 7.0 Hz), 3.783 (s, 2H), 3.750 (s, 3H), 3.7183.689 (t, 2H, J=7.0 Hz, 7.5 Hz), 3.610 (s, 1H), 3.399 (s, 1H), 3.2453.208 (m, 2H), 3.121 (s, 3H), 3.0232.779 (m, 6H), 2.569 (s, 3 H), 2.540 (s, 1H), 2.3702.338 (m, 1H), 2.250 (s, 3H), 1.9261.869 (m, 2H), 1.7884.682 (m, 3H), 1.5701.507 (m, 2H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, N-(5-Bromopentyl)phthalimide, and friends who are interested can also refer to it.

Reference:
Patent; HANGZHOU BENSHENG PHARMACEUTICAL CO., LTD.; Xu, Rongzhen; Rong, Frank; Xie, Fuwen; Lai, Hongxi; US2013/158068; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 3783-77-5, name is 2-(3-Oxobutyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C12H11NO3

To a solution of spiro[isobenzofuran-1(3H), 4′-piperidine] hydrochloride (2.80 g) and 2-(3-oxobutyl)-1H-isoindol-1,3(2H)-dione (2.0 g) in THF-methanol (1:1 v/v, 40 ml), 0.3 M sodium cyanoborohydride-1/2 zinc chloride solution in methanol (44 ml) was added and stirred for 20 hours at room temperature. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction liquid, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and condensed under reduced pressure. The resulting solid was washed with a small amount of methanol to provide 2-(3-spiro[isobenzofuran-1(3H), 4′-piperidin-1-yl]butyl-1H-isoindol-1, 3(2H)-dione (578 mg) as a white solid.

According to the analysis of related databases, 3783-77-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BANYU PHARMACEUTICAL CO., LTD.; EP1595867; (2005); A1;,
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Indoline | C8H9N – PubChem

118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, 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. HPLC of Formula: C10H9Cl2NO

2 moles of Piperazine Benzisothiazole , 1 mole of 5-(2-chloroethyl)-6- chlorooxindole in water (20 times based on benzisothiazole) and in the presence of dispersing agent. All the reactants are charged in to the flask and refluxed under nitrogen, -under stirring ^or^ r2-i6hr. After the completion “of the reaction,” the” reaction mass is cooled to room temperature and the resulting mass is filtered. It is slurried inwater and then in IPA and isolated by filtration. The solid is dried at 95- 1000C.Yield: 92%, Purity 99 %( min).

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALKEM LABORATORIES LTD.; WO2009/116085; (2009); A2;,
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Some common heterocyclic compound, 15362-40-0, name is 1-(2,6-Dichlorophenyl)-2-indolinone, molecular formula is C14H9Cl2NO, 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: C14H9Cl2NO

Pyrrole-2-carboxaldehyde (1 mmol) and 1-(chloromethyl)naphthalene (1.5 mmol) were exposed to react in the presence of NaH (1.5 mmol) in DMF (solvent) at 0 – 25 C for 45 min, the progress of the reaction was monitored with TLC. After completion, the reaction was quenched by the addition of water and the product was extracted with ethyl acetate (2 x 50 ml). The organic layers were combined, dried over Na2SO4 and distilled in vacuum to give 1-(naphthalen-1-ylmethyl)-1H-pyrrole-2-carbaldehyde (A) which was purified by column chromatography using ethyl acetate: hexane (2:48). A (1 mmol) was reacted with 1-(2,6-dichlorophenyl)-2-indolinone (1.2 mmol) in the presence of piperidine (0.2 mmol) in CHCl3/ DMF under microwave irradiations at 100 C for 1h. The progress of the reaction was monitored with TLC. After completion, the reaction was worked up by adding water and extracted with chloroform (2 x 50 ml). Combined organic layers were dried over Na2SO4 and distilled in vacuum to procure crude product 3d which was further purified by column chromatography using ethyl acetate: hexane (2:50) as eluent to get two inseparable isomers (1:2 1H NMR spectrum). Yellow Solid, yield 68 %, mp 180-182 C; IR (KBr): 2853, 3066, 1699, 1598, 1484, 1391; 1H NMR (500 MHz, CDCl3) delta: 5.78 (s, 2H, CH2 maj), 5.87 (s, 2H, CH2 min), 6.39-6.46 (m, 4H, 2ArHmaj + 2ArHmin), 6.83-6.84 (m, 1H, ArHmaj), 6.90-6.94 (m, 1H, ArHmin), 6.96 (d, J = 6.8 Hz, 1H, ArHmin), 7.0-7.01(m, 1H, ArHmin), 7.02 (d, J = 6.8 Hz, 1H, ArHmaj), 7.07-7.17 (m, 3H, 1ArHmaj + 2ArHmin), 7.21-7.24 (m, 1H, ArHmaj), 7.35-7.40 (m, 3H, 2ArHmaj + 1ArHmin), 7.41-7.45 (m, 2H, 1ArHmaj + 1ArHmin), 7.47 (s, 2H, ArHmin), 7.51(d, J = 8.0 Hz, 3H, 2ArHmaj+1ArHmin), 7.54-7.58 (m, 3H, 2ArHmaj + 1ArHmin), 7.60-7.68 (m, 2H, 1ArHmin), 7.84-7.87 (m, 3H, 2ArHmaj + 1ArHmin), 7.91-7.93 (m, 2H, ArHmaj), 7.98 (d, J = 7.78 Hz, 1H, ArHmin), 8.06 (d, J = 8.32 Hz, 1H, ArHmin), 8.35 (d, J = 7.75 Hz, 1H, ArHmaj), 8.55-8.56 (m, 1H, ArHmin); 13C NMR (125 MHz, CDCl3) delta:48.7, 49.0, 108.6, 109.0, 110.3, 110.9, 116.4, 117.3, 117.9, 120.8, 121.9, 122.0, 122.10, 122.13, 122.4, 122.5, 122.6, 122.7, 124.8, 125.0, 125.4, 125.6, 125.8, 126.1, 126.2, 126.8, 126.9, 127.1, 127.3, 128.5, 128.7, 128.75, 128.8, 128.9, 129.0, 129.1, 129.2, 130.2, 130.4, 130.5, 130.7, 130.8, 131., 132.1, 132.4, 133.6, 135.8, 136.0, 139.2, 141.3, 164.9, 167.8; HRMS (ESI) m/z for C30H20Cl2N2O [M+H]+ calcd. 495.1025, found 495.1041.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 15362-40-0, its application will become more common.

Reference:
Article; Kaur, Jagroop; Kaur, Baljit; Singh, Palwinder; Bioorganic and Medicinal Chemistry Letters; vol. 28; 2; (2018); p. 129 – 133;,
Indoline – Wikipedia,
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Reference of 205383-87-5, The chemical industry reduces the impact on the environment during synthesis 205383-87-5, name is tert-Butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, I believe this compound will play a more active role in future production and life.

To tert-butyl 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, purchased from Zerenex (50.0 mg, 0.17 mmol) in acetonitrile (1.5 mL) is added N-bromosuccinimide (30.5 mg, 0.17 mmol) and the reaction mixture is stirred for 5 h at r.t. The reaction mixture is diluted with water and saturated sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer is washed with brine, dried and concentrated in vacuo. Yield 80%, m/z 367; 369 [M+H]+

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 2-oxospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; VINTONYAK, Viktor; GRAUERT, Matthias; GRUNDL, Marc; PAUTSCH, Alexander; (64 pag.)US2016/75704; (2016); A1;,
Indoline – Wikipedia,
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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. 118289-55-7, name is 6-Chloro-5-(2-chloroethyl)indolin-2-one, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H9Cl2NO

Refluxed the reaction mixture of 5- (2-chloroethyl)-6-chloro oxindole (100 GM), 3- (1-piperazinyl)-1, 2-benzisothiazole (104.7 gm), sodium carbonate (92.2 gm), sodium iodide (6.4 gm), tetra butyl ammonium bromide (28 gm) and cyclohexane (1000 mL) till the reaction was completed. The reaction mass was cooled to a temperature of 30C and the solid was filtered. To the wet compound was added water (1000 mL) and continued stirring for 45 minutes. The solid was filtered and washed with water (100 mL). To the water wet compound was added acetone (500 mL) and there was stirring for 2 hours at room temperature. The compound was filtered and washed with acetone (200 mL) and dried at a TEMPERATURE OF70-75C to afford the CRUDE Ziprasidone base (156.9 g)

The synthetic route of 118289-55-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY’S LABORATORIES LIMITED; DR. REDDY’S LABORATORIES INC.; WO2004/50655; (2004); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 2058-72-2, name is 5-Bromo-1-methylindoline-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 2058-72-2, Application In Synthesis of 5-Bromo-1-methylindoline-2,3-dione

General procedure: To a solution of an alkyne 2 (1.2 equiv) in anhydrous toluene (3 mL) under an argon atmosphere, KOtBu (1.0 equiv) was added, and the mixture was stirred for 10-15 min. Then, an N-protected isatin 1 (1.0 equiv) was added to the reaction mixture, which was stirred for 30 min to 3 h until all the isatin was consumed (confirmed by TLC). The reaction was finally quenched with a few drops of 1 N HCl and the resulting mixture was extracted with CH2Cl2 (2 ¡Á 15 mL). The combined organic phases were washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude residue was then purified by column chromatography on silica gel (EtOAc-hexane,10:90 to 30:70) to give compounds 3.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-1-methylindoline-2,3-dione, and friends who are interested can also refer to it.

Reference:
Article; Dhara, Kalyan; Kapat, Ajoy; Ghosh, Tridev; Dash, Jyotirmayee; Synthesis; vol. 48; 23; (2016); p. 4226 – 4268;,
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Electric Literature of 169037-23-4,Some common heterocyclic compound, 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, molecular formula is C9H4F3NO3, 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.

Intermediate 1 A6-bromo-2-(trifluoromethyl)quinoline-4-carboxylic acid 300 mg (1.33 mmol) of 5-bromo-1 H-indole-2,3-dione was suspended in 3 mL water in a microwave vial. 82 mg ( 1.46 mmol) potassium hydroxide, 152 muL (2.65 mmol) acetic acid and 152 mg (1.86 mmol) sodium acetate were added so that the pH was around 5. The solution was cooled to 10 C and 238 muL (2.65 mmol) 1 ,1,1 -trifluoroacetone was added rapidly, the microwave vial was sealed and heated in the microwave for 2 h at 120 C. The reaction was stopped by the addition of 10% aqueous hydrochloric acid solution and the resulting precipitate was isolated by filtration, washed with water and dried in a vacuum drying cabinet at 50 C overnight to obtain 409 mg (1.28 mmol, 96%) of the desired title compound .In analogy to intermediate 1A, 200 mg (0.87 mmol) 5-(trifluoromethoxy)-1 H-indole-2,3-dione was heated with 388 muL (4.33 mmol) 1,1,1 -trifluoroacetone, 53 mg (0.95 mmol) potassium hydroxide, 99 muL (1.73 mmol) acetic acid and 99 mg (1.21 mmol) sodium acetate in 2 mL water for 1 h at 120 C in the microwave to obtain 269 mg (0.83 mmol, 96%) of the desired title compound after aqueous work-up.1 H NMR (400 MHz, DMSO d6): delta (ppm) = 8.01 (dd, 1 H), 8.38 (s, 1 H), 8.44 (d, 1 H), 8.85 – 8.89 (m, 1 H), 14.57 (br. s. , 1 H).

The synthetic route of 169037-23-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; SIEBENEICHER, Holger; BUCHMANN, Bernd; CLEVE, Arwed; GUeNTHER, Judith; KOPPITZ, Marcus; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; WO2015/91428; (2015); A1;,
Indoline – Wikipedia,
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