Month: June 2021

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. 611-09-6, name is 5-Nitroindoline-2,3-dione, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H4N2O4

General procedure: A mixture of isatins or acenaphthoquinone (1 mmol), activated methylene reagents (1 mmol), 1,3-dicarbonyl compounds (1 mmol) and SBA-15-DABCO (0.085 g, 7 mol%) in water was stirred at 25 or 50 C. Upon compilation, monitored by TLC (n-hexane / ethyl acetate 2 / 1), the reaction mixture was allowed to cool to room temperature. The precipitate was filtered and dissolved in acetone. The catalyst was separated by filtration of this solution. The solution was concentrated under vaccum to afford the product, which was purified by recrystallization in the ethanol.

The synthetic route of 611-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Baharfar, Robabeh; Azimi, Razieh; Synthetic Communications; vol. 44; 1; (2014); p. 89 – 100;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 20780-72-7, 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.

A 25 mL flask was charged with 2-amino-5-methyl-N?-phenylbenzohydrazide (241 mg, 1.0 mmol), 4-bromoisatins (226 mg, 1.0 mmol), CuI (10mg, 0.05 mmol), and THF (10.0 mL). The reaction mixture was stirred at reflux for 4 h before reaching completion, which was monitored by TLC. The insoluble was filtered off by a fast hot-filtration, and the product 4a was obtained directly via filtration when the mixture was allowed to cool down to the room temperature. 4.2.1. 4-Bromo-6′-methyl-3′-(phenylamino)-1’H-spiro[indoline-3,2′-quinazoline]-2,4′(3’H)-dione (4a). Yield 92percent (448 mg). Pale yellow solid, mp: 186-187 °C; 1H NMR (DMSO-d6, 400 MHz): deltaH 2.19 (s, 3H), 6.54 (d, J=8.0 Hz, 1H), 6.67 (s, 1H), 6.78-6.87 (m, 3H), 7.01 (s, 2H), 7.10-7.19 (m, 3H), 7.39 (s, 1H), 7.53 (s, 1H), 7.79 (s, 1H), 10.61 (s, 1H). 13C NMR (Acetone-d6, 100 MHz): deltaC 19.9, 80.3, 109.48, 109.54, 112.5, 113.4, 114.6, 120.2, 126.3, 126.5, 127.4, 128.1, 132.0, 132.1, 134.9, 143.87, 143.94, 148.1, 170.1, 173.8. IR (KBr): nu 3436, 3331, 3298, 1728, 1621, 1518, 1446, 1416, 1356, 1306, 1242, 1214, 1174, 1158, 1078, 1044, 989, 967, 942, 903, 777, 750, 731 cm-1. HRMS (TOF, ESI, m/z): Calcd for C22H16BrN4O2 [M-H]- 447.0457, found 447.0483.

The chemical industry reduces the impact on the environment during synthesis 4-Bromoisatin. I believe this compound will play a more active role in future production and life.

Reference:
Article; Ma, Yong-Gang; Li, Chao; Yao, Chang-Sheng; Wang, Xiang-Shan; Tetrahedron; vol. 72; 27-28; (2016); p. 3844 – 3850;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 897957-06-1, name is 6-Bromo-1-methylindolin-2-one, 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 897957-06-1, HPLC of Formula: C9H8BrNO

General procedure: Under N2, sodium ( 0.5 g ) was reacted with 30 ml ethanol. When the solution was clear,2.9 g N-Me oxindole was added followed by 3.1 g diethyl carbonate and the resulting reactionmixture was refluxed for 15 hours. Then cooled to room temperature and added to 3Nhydrochloric acid solution ( pH = 2 ). The resulting solution was extracted with ether for threeEntry Catalyst time (h) yieldb(%) drc eed(%)1 3e 5 96 72:28 38e/382 3f 8 96 74:26 21e/33 3g 2 99 73:27 11e/334 3h 8 96 71:29 6e/335 3i 2 95 59:41 1e/26 3j 10 94 68:31 44/1e7 3k 2 93 67:33 1/18 3l 72 61 69:31 8/1times. The organic extracts were combined and dried over magnesium sulfate. Thenconcentrated in vacuo and washed with petroleum ether to give 2.7 g2-oxindole-3-carboxylates 1a (61%) as light yellow solid.

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, 6-Bromo-1-methylindolin-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhou, Jing; Jia, Li-Na; Peng, Lin; Wang, Qi-Lin; Tian, Fang; Xu, Xiao-Ying; Wang, Li-Xin; Tetrahedron; vol. 70; 21; (2014); p. 3478 – 3484;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 59-48-3, name is Indolin-2-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. Quality Control of Indolin-2-one

An oven-dried 250 mL round-bottom flask containing indolin-2-one (5.00 g, 36.7 mmol) was fitted with a stirbar and septa, then flushed with nitrogen. Tetrahydrofuran (50 mL) was added and the mixture cooled to -78 . A solution of n-butyllithium in hexane (32.3 mL, 80.7 mmol, 2.5 M solution) was added, and the resulting solution was stirred at -78 for 30 minutes. Next, iodomethane (13.0 g, 91.8 mmol) was added and the mixture stirred at -78 for 10 minutes. The reaction solution was quenched with saturated aqueous ammonia hydrochloride solution. The resulting mixture was extracted with EtOAc (3 x 30 mL) and the combined organic layers were washed with brine (50 mL) , dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by chromatography on SiO2(0to 50EtOAc/petroleum ether) to afford 3-methylindolin-2-one. MS (EI) calc?d for C9H10NO [M+H]+, 148 found, 148.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 59-48-3, its application will become more common.

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

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. 334952-09-9, name is 2-Oxoindoline-6-carboxylic acid, A new synthetic method of this compound is introduced below., name: 2-Oxoindoline-6-carboxylic acid

Example 31 COMPOUND IN-023 2-Oxo-3-[5-(2-pyrrolidin-1-yl-ethoxy)-1H-indol-2-ylmethylene]-2,3-dihydro-1H-indole-6-carboxylic acid 2-Oxo-2,3-dihydro-1H-indole-6-carboxylic acid was condensed with 5-(2-pyrrolidin-1-yl-ethoxy)-1H-indole-2-carbaldehyde to give the title compound. 1H-NMR (360 MHz, DMSO-d6) delta 12.86 (s, 1H, NH), 11.11 (br s, 1H, NH), 8.01 (s, 1H, H-vinyl), 7.78 (d, J=8 Hz, 1H), 7.64 (dd, J=1.5 & 8 Hz, 1H), 7.51 (d, J=9 Hz, 1H), 7.43 (d, 1H), 7.15 (d, J=2 Hz, 1H), 7.10 (s, 1H), 4.11 (t, J=6 Hz, 2H, CH2), 2.89 (t, J=6 Hz, 2H, CH2), 2.61 (m, 4H, 2*CH2), 1.71 (m, 4H, 2*CH2). MS-Ve APC1 m/z 416.5 [M+-1].

The synthetic route of 334952-09-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tang, Peng Cho; Harris, G. Davis; Li, Xiaoyuan; US2002/52369; (2002); 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. 2436-29-5, name is 3-(1,3-Dioxoisoindolin-2-yl)propanal, A new synthetic method of this compound is introduced below., name: 3-(1,3-Dioxoisoindolin-2-yl)propanal

Example M9 N-(3-Aminopropyl)-N-{(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-pyrrol-2-yl]-2,2-dimethylpropyl}-2-hydroxyacetamide 150.0 mg (0.42 mmol) of (1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-pyrrol-2-yl]-2,2-dimethylpropan-1-amine (Intermediate C52) were initially charged in 2.0 ml of dichloromethane, and 29.2 mg (0.49 mmol) of HOAc and 125.6 mg (0.59 mmol) of sodium triacetoxyborohydride were added and the mixture was stirred at RT for 5 min. 98.9 mg (0.49 mmol) of 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propanal were added. The reaction mixture was stirred at RT overnight. The reaction mixture was diluted with ethyl acetate and the organic phase was washed twice with saturated sodium carbonate solution and once with saturated NaCl solution. After drying over magnesium sulphate, the solvent was evaporated under reduced pressure and the residue was purified on silica gel (eluent: dichloromethane/methanol 100:1). The solvents were evaporated under reduced pressure and the residue was dried under high vacuum. This gave 188.6 mg (74%) of the compound 2-[3-({(1R)-1-[1-benzyl-4-(2,5-difluorophenyl)-1H-pyrrol-2-yl]-2,2-dimethylpropyl}amino)propyl]-1H-isoindole-1,3(2H)-dione. LC-MS (Method 1): Rt=1.00 min; MS (ESIpos): m/z=541 [M+H]+.

The synthetic route of 2436-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; LERCHEN, Hans-Georg; REBSTOCK, Anne-Sophie; MARX, Leo; JOHANNES, Sarah Anna Liesa; STELTE-LUDWIG, Beatrix; DIETZ, Lisa; TERJUNG, Carsten; MAHLERT, Christoph; GREVEN, Simone; SOMMER, Anette; BERNDT, Sandra; (481 pag.)US2019/77752; (2019); 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 60434-13-1 as follows. SDS of cas: 60434-13-1

General procedure: To a flame-dried screw-capped test tube equipped with a magnetic stir bar was added I, 4,7,10,13, 16-hexaoxacyclooctadecane (0.396 g, 1.5 mmol), KF (0.087 g, 1.5 mmol) and 1- methylindoline-2,3-dione 3 (0.50 mmol). Then the screw-capped tube was evacuated and backfilled with argon. The mixture was dissolved in THF (2.0 mL) under argon atmosphere. The resultant reaction mixture was kept stirring at 30 C for 5 min. To the stirring solution was added pyridine 7 (0.75 mmol) and the aryne precursor 2 (0.75 mmol). When TLC control showed the completion of the reaction (typically after 12 h), the reaction stopped and the crude reaction mixture was purified by column chromatography on silica gel to afford the corresponding indolin 2-one derivatives 8 in good yields.

According to the analysis of related databases, 60434-13-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH; THANKAPPAN, Biju Akkattu; BHUNIA, Anup; ROY, Tony; WO2014/184808; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 7699-18-5, 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 7699-18-5 as follows.

General procedure: To the phenstatin-3-aldehyde/isocombretastatin-3-aldehyde(16a-b) (0.303 mmol/0.304 mmol) prepared in the above stepwas added corresponding substituted oxindoles (17a-h)(0.303 mmol) and catalytic amount of piperidine (1.0 ml) in ethanol.Heated the reaction mixture to reflux for 4 h at 85 C. The solidcompounds obtained in the reaction vessel were filtered and washed with ethanol for 4-5 times. After complete air drying thefinal compounds phenstatin/isocombretastatin-oxindole analogs(5a-h and 6a-h) were obtained as pure solids (yield 71-90%).

According to the analysis of related databases, 7699-18-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kumar, G. Bharath; Nayak, V. Lakshma; Sayeed, Ibrahim Bin; Reddy, Vangala Santhosh; Shaik, Anver Basha; Mahesh, Rasala; Baig, Mirza Feroz; Shareef, Mohd Adil; Ravikumar; Kamal, Ahmed; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1729 – 1740;,
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. 356068-93-4, name is (Z)-5-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 356068-93-4

To a stirred solution of compound 1 (0.5 g, 1.67 mmol) in DMF (35 mL) at room temperature was added etaOBt (1.02 g, 7.52 mmol), triethylamine(2.12 mL, 15.03 mmol), ECDIetaC1(1.44 g, 1.52 mmol) and methyl 4-aminobutanate hydrochloride(0.77 g, 5.0 mmol) successively. The mixture was stirred for 24 h at room temperature and then was diluted with water (20 mL), brine (20 mL) and saturated bicarbonate solution (20 mL) and the peta of solution was adjusted to 11-12 with 10 mol/L NaOH. The mixture was filtrated, the solid was collected, washed with water and dried to obtain crude yellow solid product 110-3 (0.32 g, 48.3%). LCMS: m/z 400(M+l), 1U NMR(DMSO-J6) deltal.77 (m, 2eta), 2.39 (m, 4H), 2.42 (s, 3H), 2.49 (s, 3H), 3.23 ( t, 2H), 6.85 (m, 2H), 7.60 (t, IH), 7.67 (s, IH), 7.71 (m, IH), 10.89 (s, IH), 13.68 (s, IH).

According to the analysis of related databases, 356068-93-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CURIS, INC.; WO2008/33747; (2008); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 320734-35-8, A common heterocyclic compound, 320734-35-8, name is 7-Bromooxindole, molecular formula is C8H6BrNO, 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 cooled (-78C) solution of 7-bromooxindole (4.7g; 22.16 mmol) and N,N,N?, N?tetramethylethylenediamine (10.97 mL; 73.17 mmol) in dry THF (230 mL) was slowly added n-butyllithium solution (19.S mL; 48.76 mmol; 2.S M in hexane). The solution was stirred for 30 minutes at the same temperature and then, iodomethane (1.65 mL; 26.6 mmol) was added slowly. The reaction mixture was stirred at -20C for 1.5h, then,quenched with a saturated aqueous solution of NH4C1 and extracted with EtOAc.The organic layer was sried over MgSO4, filtered and concentrated in vacuo. The resultingcrude material was purified by silica gel chromatography (mobile phase: heptane/EtOAc)to afford, after solvent evaporation, 1.3 g (22%) of intermediate 217.

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; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (419 pag.)WO2018/2219; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem