Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-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 5332-26-3, Application In Synthesis of 2-(Bromomethyl)isoindoline-1,3-dione

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).

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:
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);,
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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. 20780-72-7, name is 4-Bromoisatin, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Bromoisatin

To a solution of 4-bromoisatin 30 (200 mg, 0.88 mmol) in THF/water (3:1, 3 mL) was added potassium 3-thienyltrifluoroborate (235 mg, 1.24 mmol) and K3PO4 (675 mg, 3.19 mmol) followed by Pd(PPh3)2Cl2 (62 mg, 0.09 mmol). The reaction vessel was sealed and heated by microwave irradiation for 4 h at 130 ¡ãC. The reaction mixture was cooled to rt, diluted with EtOAc (10 mL) and filtered through Celite?. The organic solution was washed with brine (10 mL) and the resulting aqueous layer was further extracted with EtOAc (2*). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo to give the crude product. The product was purified via flash column chromatography (eluent 30-40 ¡ãC petrol/acetone, 4:1) to afford the title compound (43) as an orange solid (120 mg, 59percent); mp 213-216 ¡ãC; numax (solid) 3098, 2927, 1727, 1584; deltaH (500 MHz, DMSO-d6) 6.85 (1H, dd, J = 7.9, 0.6 Hz, C(7)H), 7.20 (1H, dd, J = 7.9, 0.6 Hz, C(5)H), 7.50 (1H, dd, J = 4.9, 1.3 Hz, C(4′)H), 7.58 (1H, app t, J = 7.9 Hz, C(6)H), 7.62 (1H, dd, J = 4.9, 2.9 Hz, C(5′)H), 8.07 (1H, dd, J = 2.9, 1.3 Hz, C(2′)H), 11.13 (1H, br s, NH); deltaC (125 MHz, DMSO-d6) 110.8, 113.9, 123.8, 125.6, 126.3, 128.4, 135.8, 137.2, 138.0, 151.6, 158.9, 183.0; m/z (ESI-) 228 ([M-H]-, 100percent); HRMS (ESI-) C12H6N4O2S- ([M-H]-) requires 228.0125; found 228.0127.

According to the analysis of related databases, 20780-72-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gianella-Borradori, Matteo; Christou, Ivy; Bataille, Carole J.R.; Cross, Rebecca L.; Wynne, Graham M.; Greaves, David R.; Russell, Angela J.; Bioorganic and Medicinal Chemistry; vol. 23; 1; (2015); p. 241 – 263;,
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Electric Literature of 6780-38-7,Some common heterocyclic compound, 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, molecular formula is C10H6ClNO3, 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 tert-butyl 3-amino-4-methylphenylcarbamate (0.667 g, 3 mmol), 2-(l,3-dioxoisoindolin-2-yl)acetyl chloride (0.671 g, 3.00 mmol) in DCM (10 mL) was added diisopropylethylamine (1.048 mL, 6.00 mmol). After stirring 25 C for 15 h, saturated aqueous sodium chloride (25 mL) was added and extracted with ethyl acetate (3 x 25 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated. The crude product was purified by silica gel chromatography (100% ethyl acetate) to give the title compound as a white solid (1.15 g, 2.81 mmol, 94% yield); 1H NMR (400 MHz, DMSO-d6) delta 9.70 (s, IH), 9.29 (s, IH), 7.91 – 7.99 (m, 2H), 7.83 – 7.91 (m, 2H), 7.56 (s, IH), 7.13 (d, J= 8.20 Hz, IH), 7.07 (d, J- 8.20 Hz, IH), 4.45 (s, 2H), 2.11 (s, 3H), 1.45 (s, 9H).

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

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2009/89042; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6326-79-0, These common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, 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 the reaction vessel, 6-bromoisatin (10.0 g, 22 mmol) and 1N aqueous NaOH solution (48 mL) were added and the mixture was heated to 50C and stirred for 1 hour. The reaction solution was cooled to 0C, and a mixture of sodium nitrite (3.0 g, 22 mmol) and water (11 mL) was added slowly. Water (90 mL) and sulfuric acid (4.6 mL) were slowly added to the mixture at the same temperature and stirred. To the reaction mixture was added a mixture of tin chloride dihydrate (24.0 g, 53 mmol) and hydrochloric acid (40 mL) at 0 C, and the mixture was stirred at room temperature. The resulting solid was filtered, washed with water and dried to give the desired compound (8.53 g, 80% yield) as a yellow solid.

Statistics shows that 6-Bromoisatin is playing an increasingly important role. we look forward to future research findings about 6326-79-0.

Reference:
Patent; Korea Institute of Science and Technology; Sim Tae-bo; Noh Eun-ju; Yang Han-yong; (33 pag.)KR101936851; (2019); B1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

These common heterocyclic compound, 2058-72-2, name is 5-Bromo-1-methylindoline-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. Safety of 5-Bromo-1-methylindoline-2,3-dione

General procedure: DABCO (0.112 g, 1.00 mmol) was added to a solution of 2a (0.08 g, 0.5 mmol), phenol (0.094 g, 1.00 mmol) and 1a (0.147 g, 1.00 mmol) in acetonitrile (0.5 mL), and the reaction was kept for 2 days. The reaction mixture was then directly subjected to column chromatography (EtOAc/Hexane, 3:10) to obtain the product 3aa as a yellow solid (0.142 g) at 92% yield.

The synthetic route of 5-Bromo-1-methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Singh, Radhey M.; Bharadwaj, Kishor Chandra; Tiwari, Dharmendra Kumar; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 2975 – 2980;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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 3-7 have been synthesized using a procedure originallyreported by Roehrig et al.16 Chiral amine or amino alcohol(0.6 mmol, 1.2 equiv) in 10 mL isopropanol was added to the solutionof (R)-N-(2,3-epoxypropyl)phthalimide (102 mg, 0.50 mmol)in 10 mL of isopropanol at in an ice bath and stirred for 1 h. thenrefluxed for 12 h. The reaction monitored by TLC. Solvent was removed by rotary evaporator under reduced pressure after completionof the reaction.

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; Karakaplan, Mehmet; Jameel, Basam; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 597 – 602;,
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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 5-Bromoisoindoline-1,3-dione

General procedure: To a solution of NBP (1.5 mmol, 0.339 g) and DBU (1.5 mmol, 0.218 mL) in MeCN (2.0 mL), ethyl phenylphosphinate 1a (1.0 mmol, 0.154 mL) was added. The reaction mixture was stirred at 0 C for 10 min. After the starting material 1a was consumed as indicated by TLC, the reaction mixture was poured into water and then extracted with CH2Cl2 (3 x 10 mL). The combined organic phase was washed with water (3 x 10 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, petroleum ether: ethyl acetate = 3:1) to give 2a (268 mg, 85%) as a white solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 6941-75-9.

Reference:
Article; Li, Yueju; Liang, Fushun; Tetrahedron Letters; vol. 57; 26; (2016); p. 2931 – 2934;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. name: 2-(Bromomethyl)isoindoline-1,3-dione

3.5 g (87 mmol) of sodium hydride are added in portions to a solution of 25 g (87 mmol) of dimethyl2- (4- ert-butoxycarbonylpiperazin-l-yl) malonate in 250 ml of tetrahydrofuran cooled to 2C. The reaction medium is stirred at ambient temperature for 30 minutes, then brought to 2C before dropwise addition of 21 g (87 mmol) of 2- (bromomethyl) isoindole-1, 3-dione in 200 ml of tetrahydrofuran . The reaction medium is stirred at ambient temperature for 20 h, treated by addition of 500 ml of water then extracted with ethyl acetate. The organic phase is dried over magnesium sulphate, filtered and concentrated under vacuum.The crude product obtained is purified by chromatography over silica gel eluted with a 70/30 heptane/ethyl acetate mixture. 27.5 g (73%) of dimethyl 2- (4- ert-butoxycarbonylpiperazin-l-yl) -2- (1, 3-dioxo- 1, 3-dihydro-isoindol-2-ylmethyl) malonate are obtained in the form of a white solid.

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

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT; CHAMBON, Sandrine; CLARY, Laurence; SCHUPPLI, Marlene; WO2011/33009; (2011); A1;,
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. 552330-86-6, name is 5-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

A solution of 5-bromoisoindolin-1-one (2.0 g, 9.4 mmol) , N, N-dimethylpyridin-4-amine (0.23 g, 1.9 mmol) and di-tert-butyl dicarbonate (2.47 g, 11.3 mmol) in DMF (20 ml) was stirred at ambient temperature for 2 h. Water (100 mL) was then added and the mixture was extracted with EtOAc (3×30 mL) . The combined organic fractions were washed with brine (3×10 mL) , dried (Na2SO4) , filtered and the solvent evaporated under reduced pressure. The residue was purified by chromatography on SiO2(1-90EtOAc/isohexane) to give tert-butyl 5-bromo-1-oxoisoindoline-2-carboxylate. MS (EI) calc?d for C13H15BrNO3[M+H]+, 312 found, 312.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; ACHAB, Abdelghani Abe; CHRISTOPHER, Matthew P.; FRADERA LLINAS, Francesc Xavier; KATZ, Jason D.; METHOT, Joey L.; ZHOU, Hua; XU, Shimin; FU, Jianmin; FU, Ning; LI, Yabin; WANG, Xichao; (228 pag.)WO2017/166104; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6326-79-0,Some common heterocyclic compound, 6326-79-0, name is 6-Bromoisatin, 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 1: Synthesis of Intermediate 1-12.1 To R27 (25.0 g, 111 mmol) in acetonitrile (750 mL) is added Mel (15 niL, 241 mmol) and K2C03 (60.0 g, 434 mmol) and the reaction mixture is stirred at 60 C for 2 h. The reaction mixture is filtered and concentrated. Water and ethyl acetate are added to the residue. The organic layer is extracted twice with water, dried over MgS04 and concentrated. Yield 56%, m/z 240/242 [M+H]+, rt 0.48 min, LC-MS Method X001 004.

The synthetic route of 6326-79-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ANDERSKEWITZ, Ralf; GRAUERT, Matthias; GRUNDL, Marc; HAEBEL, Peter, Wilhelm; OOST, Thorsten; PAUTSCH, Alexander; PETERS, Stefan; BINDER, Florian; VINTONYAK, Viktor; WO2014/140075; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem