Tag: M.W=200-300

Electric Literature of 181140-34-1, 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 181140-34-1 as follows.

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.

According to the analysis of related databases, 181140-34-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Karakaplan, Mehmet; Jameel, Basam; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 597 – 602;,
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Related Products of 169037-23-4, The chemical industry reduces the impact on the environment during synthesis 169037-23-4, name is 5-(Trifluoromethoxy)indoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of beta-nitrostyrenes, isatin and tyrosine (1:1:1) was stirredunder heating at 100 C for 1 h in [bmim]Br (200 mg). After the reaction was completed, 10 mL of ethyl acetate was added to the reaction mixture and stirred for 15 min. The organic layer was separated, washed with water, and dried. The cycloadduct was further purified using hexane: ethyl acetate (3:2 v/v) as eluent employing column chromatography technique. After extraction of the cycloadduct, [bmim]Br wasdried under vacuum at 80 C for 2 h to exclude any water trapped from moisture and reused for subsequent runs.

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, 5-(Trifluoromethoxy)indoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kumar, Raju Suresh; Almansour, Abdulrahman I.; Arumugam, Natarajan; Mohammad, Faruq; Kotresha; Menendez, J. Carlos; Bioorganic and Medicinal Chemistry; vol. 27; 12; (2019); p. 2487 – 2498;,
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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. 87-48-9, name is 5-Bromoindoline-2,3-dione, A new synthetic method of this compound is introduced below., Formula: C8H4BrNO2

General procedure: TiCl4 (0.7 mL, 6 mmol) wasadded to a stirred suspension of Zn powder (0.78 g, 12 mmol) infreshly distilled anhydrous THF (15 mL) at room temperature (r.t.)under a dry N2 atmosphere. After completion of the addition, themixture was refluxed for 2 h. The suspension of the low-valent titaniumreagent formed was cooled to r.t. A solution of isatin derivatives(2 mmol) in THF (10 mL)was added dropwise. The mixturewas stirred at room temperature for about 5 min under N2. Afterthis period, the thin layer chromatography (TLC) analysis of themixture showed the reaction completed. The reaction mixture wasquenched with 5% HCl (15 mL) and extracted with CH2Cl2(3 x 50 mL). The combined extracts were washed with water (350 mL) and dried over anhydrous Na2SO4. After evaporation of thesolvent under reduced pressure, the crude product was purified bycolumn chromatography (petroleum ether/EtOAc = 5:1) to give thepure products 9a-d.

The synthetic route of 87-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Delong, Wang; Lanying, Wang; Yongling, Wu; Shuang, Song; Juntao, Feng; Xing, Zhang; European Journal of Medicinal Chemistry; vol. 130; (2017); p. 286 – 307;,
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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;,
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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. 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;,
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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;,
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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;,
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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. 6326-79-0, name is 6-Bromoisatin, A new synthetic method of this compound is introduced below., category: indolines-derivatives

The conversion of substituted isatins to substituted Indazole-3- carboxylic acids is essentially the same methods as described by Snyder, H. R. et al. Thus, the substituted isatin (17-1) was suspended in IN NaOH and was heated at 50C for 30 min. The burgundy solution was allowed to cool to room temperature and was maintained for an additional one hour. The reaction mixture was cooled to 0 C and was treated with a solution of NaN02 (22 mmol) in water. This solution was added through a pipet submerged below the surface of H2S04 in water at 0c in 15 min. The reaction was maintained for an additional 30 min. A cold solution of Tin(II) chloride in con. HC1 was added to the reaction mixture over 10 min and the reaction mixture was stirred at the same temperature for an additional 2h. The solid filtered and washed with water several times and dried in vacuo to give quantitative mass balance of the product (17-2) with 80% NMR purity.

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; FENG, Yangbo; CHEN, Yen Ting; SESSIONS, Hampton; MISHRA, Jitendra K.; CHOWDHURY, Sarwat; YIN, Yan; LOGRASSO, Philip; LUO, Jun-Li; BANNISTER, Thomas; SCHROETER, Thomas; WO2011/50245; (2011); A1;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 87-48-9, name is 5-Bromoindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. name: 5-Bromoindoline-2,3-dione

General procedure: To a mixture of isatin (7a-e, 1.0 g) and hydrazine-hydrate (5 mL, ~30 mmol) in ethylene glycol,potassium hydroxide (10 equiv.) was added and the resulting reaction mixture was stirred at110-130 C for 2-3 h (monitored by TLC). The reaction mixture was cooled to roomtemperature, poured into ice-cold water (50 mL), acidified to pH 2 with 6N hydrochloric acidand extracted with ethyl acetate (3 x 30 mL). The organic extracts were combined, washed withbrine (15 mL), dried over sodium sulfate and concentrated in vacuo. The obtained residue waspurified by column chromatography using ethyl acetate-hexane as eluents to furnish 8a-e inmoderate yields.

The synthetic route of 87-48-9 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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Related Products of 264916-06-5, 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. 264916-06-5, name is tert-Butyl 5-aminoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of (R)-1-(3-((2-chloro-5-(trifluoromethyl)pyrimidin-4-yl) amino)piperidin- 1-yl)prop-2-en-1-one (64.2) (100 mg, 0.3 mmol), tert-butyl 5-aminoisoindoline-2-carboxylate (1.5) (64 mg, 0.27 mmol), Cs2CO3 (177 mg, 0.54 mmol), tris(dibenzylideneacetone)dipalladium(0) (25 mg, 0.03 mmol), and Davephos (10 mg, 0.03 mmol) in tert-amyl alcohol (10 mL) was stirred at 100 C for 3 h. The mixture was quenched with the addition of water and extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated to dryness to afford the crude product. The crude product was purified by column chromatography (hexanes/ethyl acetate: 1/1) to afford (R)-1-(3-((2-(isoindolin-5-ylamino)-5-(trifluoromethyl)pyrimidin-4- yl)amino)piperidin-1-yl)prop-2-en-1-one (I-65).The product was taken up in DCM/TFA (5 mL/3 mL) and stirred at room temperature for 30 min. The mixture was concentrated to dryness to afford the TFA salt of (R)-1-(3-((2- (isoindolin-5-ylamino)-5-(trifluoromethyl)pyrimidin-4-yl)amino)piperidin-1-yl)prop-2-en-1-one (I-65) as a white solid (35 mg, 21%). [00915] LCMS: 433.1 [M+1]+. [00916] 1HNMR (400 MHz, CD3OD): delta 1.58-1.61 (m, 1H), 1.86-1.91 (m, 2H), 2.03-2.09 (m, 1H), 2.88-2.96 (m, 0.5H), 3.04-3.10 (m, 0.5H), 3.15-3.22 (m, 0.5H), 3.26-3.27 (m, 0.5H), 3.98- 4.10 (m, 1H), 4.29-4.39 (m, 1.5H), 4.49-4.63 (m, 4.5H), 5.47 (d, 0.5H), 5.84 (d, 0.5H), 6.05 (d, 0.5H), 6.28 (d, 0.5H), 6.40 (dd, 0.5H), 6.86 (dd, 0.5H), 7.36-7.39 (m, 1H), 7.58 (dd, 1H), 7.81 (s, 1H), 8.24 (d, 1H).

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

Reference:
Patent; CELGENE AVILOMICS RESEARCH, INC.; SCHWARTZ, C., Eric; SURAPANENI, Sekhar, S.; WORM, Karin Irmgard; (266 pag.)WO2016/90079; (2016); A1;,
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