Month: May 2021

These common heterocyclic compound, 3484-35-3, name is 5-Methylindolin-2-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. Quality Control of 5-Methylindolin-2-one

General procedure: To a solution of appropriate oxindole (8a-e, 0.3 mmol) in ethanol (3 mL) was addedcorresponding aldehyde (12a-h, 0.32 mmol) and a catalytic amount of piperidine. The reactionmixture was stirred at reflux for 6-12 h (monitored by TLC). After cooling, the precipitate wasfiltered, washed with cold ethanol, and dried in air to furnish pure (Z)-3-(4′-(aminoalkoxy)-3′-methoxybenzylidene)indolin-2-one title compounds of formula (5a-t) as yellow/brown/orangesolids in moderate to excellent yields.

The synthetic route of 5-Methylindolin-2-one has been constantly updated, and we look forward to future research findings.

Reference:
Article; Senwar, Kishna Ram; Reddy, T. Srinivasa; Thummuri, Dinesh; Sharma, Pankaj; Bharghava, Suresh K.; Naidu; Shankaraiah, Nagula; Bioorganic and Medicinal Chemistry Letters; vol. 26; 16; (2016); p. 4061 – 4069;,
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1127-59-9, name is 7-Methylindoline-2,3-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. category: indolines-derivatives

Preparation of 7-bromomethylisatin The 7-methylisatin (16.1 g, 0.1 mole) is suspended in dichloroethane (2000 ml) and the suspension is heated and irradiated with a high intensity light source to the reflux point. Bromine (24.3 g, 0.15 mole) is added dropwise over a one hour period. The solution is filtered hot and concentrated at reduced pressure to yield the product as an orange solid after washing with anhydrous diethyl ether. The product is purified using flash chromatography on silica (elution with 24:1 dichloromethane:diethyl ether) to afford after drying (at 60° C. at 0.1 mm); 7-bromomethylisatin, mp 199°-200° C. dec.

The synthetic route of 1127-59-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US4530929; (1985); A;,
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Synthetic Route of 19727-83-4, A common heterocyclic compound, 19727-83-4, name is 6-Nitroindoline, molecular formula is C8H8N2O2, 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 6-nitroindoline (a) (3 g, 18.3 mmol) in DCM (30mL) was added di-tert-butyl dicarbonate (4.8 g, 22 mmol) and TEA (3.7 g, 36.6 mmol). The solution was stirred for 5 h at room temperature then washed with water and brine. The organic layer was dried, filtered and concentrated. Silica gel column chromatography provided tert-butyl 6-nitroindoline-l-carboxylate (b) as a white solid (2.4 g, 50%).

The synthetic route of 19727-83-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ISOCURE BIOSCIENCES INC.; ZHANG, Tinghu; CHE, Jianwei; (118 pag.)WO2018/71404; (2018); A1;,
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Some common heterocyclic compound, 391-12-8, name is 7-(Trifluoromethyl)isatin, molecular formula is C9H4F3NO2, 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. Recommanded Product: 391-12-8

EXAMPLE 6 20 parts of a 30 percent strength by weight solution of sodium methylate in methanol are added to 21.5 parts of 7-trifluoromethylisatin in 300 parts of methanol at 0° C., resulting in a violet solution. 8 parts of a 50 percent strength by weight hydrogen peroxide solution are then added at 0° C., after which the mixture is stirred for one hour at room temperature. The reddish solution is concentrated, water is added, the pH is brought to 8 with hydrochloric acid and the batch is extracted by shaking with methylene chloride. After concentrating the methylene chloride phase, 16.2 parts (74percent of theory) of methyl 3-trifluoromethylanthranilate are obtained. H1 –NMR (CDCl3): delta=3.8 ppm (s), 6.4 (s, N–H2), 6.6 (t), 7.5 (d) and 7.95 (d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 391-12-8, its application will become more common.

Reference:
Patent; BASF Aktiengesellschaft; US4310677; (1982); A;,
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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. 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H4ClNO2

To a solution of 5-chloro-isoindole-l,3-dione (5.0 g, 27.5 mmol) in DCM (200 mL) was added ethylmagnesium chloride (2 M in THF, 41.3 mL) dropwise at 0 C. After the addition, the mixture was allowed to stir at 0 C for 3 hours before it was quenched with satd. aq. NH4C1 solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product containing a mixture of two regioisomers (5.82 g, 100%). MS: 212.0 (M+H+).

According to the analysis of related databases, 7147-90-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
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Related Products of 7699-18-5, These common heterocyclic compound, 7699-18-5, name is 5-Methoxyindolin-2-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.

General procedure: A suspension of indolinone (0.3mmol), aldehyde (0.3mmol) and pyridine (30muL) in methanol (1mL) were heated under microwave irradiation at 100 C for 30 minutes. The reaction mixture was cooled to room temperature and the resulting precipitate was removed by filtration, carefully washed with methanol and dried in vacuo. When no precipitate was observed methanol was removed under vacuum and the residue was purified by silica gel chromatography to give the desired product.

The synthetic route of 7699-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Goering, Stefan; Taymans, Jean-Marc; Baekelandt, Veerle; Schmidt, Boris; Bioorganic and Medicinal Chemistry Letters; vol. 24; 19; (2014); p. 4630 – 4637;,
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Related Products of 6941-75-9, 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. 6941-75-9 name is 5-Bromoisoindoline-1,3-dione, 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.

Heck reaction of 4-Bromophthalic imide with 1,7-Octadien (Heck condition) 1 g 4-Bromophthalic imide (6.167 mmol), a two-fold excess 1,7-Octadien (12.33 mmol) and the catalysator system were solved in 50 ml DMF. The catalysator system consisted of Palladiumacetate (5 mol-% to Imide: 0.31 mmol), 0.92 mmol Triphenylphosphane and 6.17 mmol Triethylamin. The solution has been heated for 24 h at 150 C (Control of reaction progress via thin layer chromatography with CH2Cl2: n-Hexane [5:1]). From the resulting dark brown solution the solvent was removed by reduced pressure. The obtained viscous brown raw product was solved with 80 ml CH2Cl2 and washed three times (3 x 200 ml) with a saturated H2O/NaCl solution. After that the CH2Cl2-phase was dried with MgSO4 and the solvent was removed by reduced pressure. The viscous brown product (1) was dried under constant vacuum.Yield : quant. IR : v 1772, 1717 (s, Imide) cm-1 MS / ESI : 401.14972 m/z (M+H+)

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

Reference:
Patent; DENTSPLY DETREY GmbH; E, Klee, Joachim; Retzmann, Nils; Ritter, Helmut; Szillat, Florian; EP2759289; (2014); A1;,
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Indoline | C8H9N – PubChem

Synthetic Route of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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 8: 6-((R)-5-{[((RS)-2-methoxy-8,9-dihydro-furo[2,3-Lambda]quinolin-9-ylmethyl)- amino] -methyl}-2-oxo-oxazolidin-3-yl)-4H-benzo [ 1 ,4] thiazin-3-one:; 8.i. rac-3-( 1 ,3-dioxo- 1 ,3-dihydro-isoindol-2-yl)-2-(7-fluoro-2-methoxy-quinolin-8-yl)- propionic acid methyl ester:; To a solution of LiEtaMDS (IM in TEtaF, 9.6 niL) was added at -78C a solution of (7-fluoro-2-methoxy-quinolin-8-yl)-acetic acid methyl ester (2.0 g, 8.0 mmol; prepared as in WO 2007/081597) in TEtaF (16 mL) over lO min. After stirring the resulting orange mixture for 1 h at -78C, a solution of Lambda/-(bromomethyl)phthalimide (1.2 eq.) in TEtaF (16 mL) was added dropwise over 10 min. The mixture was stirred 1 h at -78C and then at it overnight. The yellow solution was quenched with 17V EtaC1 (80 mL) and then extracted with DCM. The combined org layers were washed with water, dried over MgSO4, concentrated and purified by CC (Etaept/EA 1 : 1) to give 1.89 g of a yellow solid which was recrystallized from EA/MeOEta/NEta4OEta (90:10:1) to afford the title intermediate as a colourless solid (924 mg, 28% yield). MS (ESI, m/z): 409.3 [IVB-H+].

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

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HUBSCHWERLEN, Christian; RUEEDI, Georg; SURIVET, Jean-Philippe; ZUMBRUNN ACKLIN, Cornelia; WO2010/15985; (2010); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 5332-26-3 as follows. COA of Formula: C9H6BrNO2

General procedure: S-alkylation of the products was achieved by following a modified method [38]. The oxadiazoles (6a, 6b, 13) (0.02, mol) and K2CO3 (0.022, mol) were stirred in 10mL of acetone for 20 mints followed by the addition of alkyl bromides 7a-c and 7d-m (0.022, mol). The reaction mixture was stirred for 4-6h at room temperature. The reaction mixture was concentrated under vacuum and crude solid gained was recrystallized from methanol to get pure products. 8a: Colorless solid; 55% yield; Rf: 0.55 (chloroform: acetone, 9:1), m.p.; 224-226C; 1H NMR (300MHz, DMSO-d6): delta ppm 10.71 (s, 1H, NH), 7.91-7.84 (m, 4H, Ar-H), 7.64 (dd, 4H, J=18, 9Hz, Ar-H), 7.28 (d, 2H, J=9Hz, Ar-H), 7.06 (d, 2H, J=9Hz, Ar-H), 5.28 (s, 2H, SCH2N), 2.31 (s, 3H, Ar-CH3); 13C NMR (75MHz, DMSO-d6): delta ppm 167.02, 166.74, 160.01, 144.00, 142.03, 140.01, 135.44, 131.76, 129.72, 127.89, 126.94, 124.06, 119.95, 118.11, 43.00, 21.37; IR (cm-1) 3260 (N-H), 3025 (C-H, aromatic), 2948 (C-H, aliphatic), 1716 (C=O), 1602 (C=N), 1308, 1176 (O=S=O); Anal. Calcd for C24H18N4O5S2: C, 56.91; H, 3.58; N, 11.06; O, 15.79; S, 12.66 Found: C, 56.98; H, 3.61; N, 11.11; O, 15.79; S, 12.72.

According to the analysis of related databases, 5332-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Batool, Farwa; Hamdani, Syeda Shamila; Hameed, Shahid; Khan, Bilal Ahmad; Mughal, Ehsan Ullah; Saeed, Muhammad; Saleem, Hafiza Nosheen; Bioorganic Chemistry; vol. 96; (2020);,
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Related Products of 603-62-3, 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 603-62-3 as follows.

4-Nitro-lH-isoindole-l, 3(2H)-dione (117.3 g; Formula IV) followed by 1,1- carbonyldiimidazole (138.1 g) were added to a slurry of 3-aminopiperidine-2,6-dione hydrochloride (100 g, Formula III; obtained in Example 1) in acetonitrile (800 mL) to obtain a reaction mixture. The reaction mixture was heated to reflux at 80C to 82C and then stirred for 2 hours. 1,1-Carbonyldiimidazole (19.8 g) was further added to the reaction mixture twice over an interval of one hour. The reaction mixture was cooled to 25 C to 30C and then stirred for 30 minutes. The product obtained was filtered and the wet solid obtained was dried at 50C to 55C under reduced pressure to obtain the title compound. (0076) Yield: 162 g (88%)

According to the analysis of related databases, 603-62-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUN PHARMACEUTICAL INDUSTRIES LIMITED; BARMAN, Dhiren Chandra; RAM, Sita; RAJBANGSHI, Mantu; NATH, Asok; PRASAD, Mohan; (14 pag.)WO2018/154516; (2018); A1;,
Indoline – Wikipedia,
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