Month: June 2021

Synthetic Route of 667463-64-1, 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 667463-64-1 as follows.

General procedure: Step 1: To a 250 mL flask equipped with a silicone oil bubbler was added commercially available isatin (7.7 g, 50 mmol) and anhydrous DMF (80 mL). the mixture was cooled down to 0 oC. To this solution was added NaH (1.32 g, 55 mmol), followed by the addition of CH3I in 15 min. Upon completion of the reaction (monitored by TLC), the mixture was diluted with saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated to yield the crude N-methylindoline-2, 3-dione, which was used directly in the next step. Step 2: The N-methylindoline-2, 3-dione (7.58 g, 47 mmol) was refluxed in NH2·NH2-H2O ( 35 %) for 1h. Then the mixture was cooled to rt. The crude product was extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, purified by flash chromatography on silica gel (petroleum ether/ethyl acetate = 10:1). 1-Methylindolin-2-one was obtained as a pink solid.

According to the analysis of related databases, 667463-64-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhao, Jian-bo; Ren, Xinfeng; Zheng, Bu-quan; Ji, Jian; Qiu, Zi-bin; Li, Ya; Journal of Fluorine Chemistry; vol. 215; (2018); p. 44 – 51;,
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897957-06-1, name is 6-Bromo-1-methylindolin-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. SDS of cas: 897957-06-1

A solution of {S)-tert-hvXy 4-(l-amino-l-oxo-3-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 16, step (i), 200 mg) and 6-bromo-l-methylindolin-2-one (87 mg) in acetonitrile (5 mL) was treated with potassium carbonate (107 mg) and purged with nitrogen. 1,1 bis(Di-tert- butylphosphino)ferrocene palladium dichloride (15 mg) was added and the reaction stirred under reflux under nitrogen for 4 h and then evaporated in vacuo. The residue was partitioned between water (40 mL) and ethyl acetate (40 mL). The aqueous was further extracted with ethyl acetate (40 mL) and the combined organic extracts were dried over magnesium sulfate and evaporated in vacuo. The crude product was purified by flash silica chromatography eluting with ethyl acetate. Pure fractions were evaporated to dryness to afford the sub-titled compound (45 mg).1H NMR (399.824 MHz, CDCl3) delta 7.54 (d, 2H), 7.32 – 7.28 (m, 3H), 7.22 (d, IH), 6.97 (s, IH), 6.88 – 6.80 (m, IH), 6.49 (d, IH), 5.27 (s, IH), 4.90 (s, IH), 4.80 (q, IH), 3.89 – 3.82 (m, IH), 3.69 – 3.62 (m, IH), 3.60 – 3.48 (m, 4H), 3.32 – 3.18 (m, 5H), 2.33 – 2.24 (m, IH), 1.92 – 1.76 (m, 2H), 1.35 (s, 9H).m/e (Multimode+) 437 [M+2H-BOC]+

The synthetic route of 897957-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; FORD, Rhonan; METE, Antonio; MATHER, Andrew; MILLICHIP, Ian; WO2010/128324; (2010); A1;,
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Related Products of 6872-06-6, These common heterocyclic compound, 6872-06-6, name is 2-Methylindoline, 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.

2-methylindoline (3.26 g, 24.5 mmol) and hexane (0.536 M, 45.7 ml) were placed in a 100 ml Schlenk flask. At -20 C, n-BuLi (1.1 eq, 10.8 ml) was added and allowed to stand at room temperature overnight. Filtered through glass frit (G4) and vacuum dried to obtain phosphine-amine lithium. The phosphine-amine lithium (3.37 g, 24.2 mmol) was added to diethyl ether (0.423 M, 57.3 ml) in a 250 ml Schlenk flask and CO2 bubbling was added at -78 C for 1 hour. THF (1.1 eq, 2.16 ml) and t-BuLi (1.1 eq, 15.7 ml) were added at -20 C and kept at this temperature for 2 hours. IPr2PCl (0.85 eq, 3.14 g) and diethyl ether (0.359 M, 57.3 ml) were added at the same temperature and maintained at the same temperature for 1 hour. After slowly reacting at room temperature overnight, 50 ml of distilled water was added at 0 C, and the mixture was stirred at room temperature for 30 minutes. Work-up with diethyl ether, drying over MgSO4, and then red oil was obtained in 2.23 g, 37% yield via hexane, diethyl ether 50: 1 column

The synthetic route of 6872-06-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LG CHEM, LTD.; JANG, Jae Kwon; KIM, Seul Ki; PARK, In Sung; LEE, Eun Jung; LEE, Choong Hoon; HAN, Ki Won; HAN, Hyo Jung; (20 pag.)KR2017/68330; (2017); A;,
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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 65435-04-3 as follows. Safety of 5-(2-Chloroacetyl)indolin-2-one

A suspension of 9.3 g of 5-chloroacetyl-2-oxindole was stirred in 90 ML pyridine at 80 to 90 C. for 3 hours then cooled to room temperature.. The precipitate was collected by vacuum filtration and washed with 20 ML ethanol.. The solid was dissolved in 90 ML 2.5N sodium hydroxide and stirred at 70 to 80 C. for 3 hours.. The mixture was cooled to room temperature and acidified to PH 2 with 0.5 N hydrochloric acid.. The precipitate was collected by vacuum filtration and washed thoroughly with water to give crude 5-carboxy-2-oxindole as a dark brown solid.. After standing overnight the filtrate yielded 2 g of 5-carboxy-2-oxindole as a yellow solid.. The crude dark brown product was dissolved in hot methanol, the insoluble material removed by filtration and the filtrate concentrated to give 5.6 g of 5-carboxy-2-oxindole as a brown solid.. The combined yield was 97%.

According to the analysis of related databases, 65435-04-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sugen, Inc.; US6350754; (2002); B2;,
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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. 193354-13-1, name is 5-Iodoindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Iodoindolin-2-one

5-Methoxycarbonyl-2-oxindole 5-Iodo-2-oxindole (17 g) was refluxed with 2 g of palladium diacetate, 18.2 g of triethylamine, 150 mL of methanol, 15 mL of dimethylsulfoxide and 2.6 g of DPPP in an atmosphere saturated with carbon monoxide. After 24 hours, the reaction was filtered to remove the catalyst and the filtrate concentrated. The concentrate was chromatographed on silica gel (30% ethyl acetate in hexane). The fractions containing product were concentrated and allowed to stand. The precipitated product was collected by vacuum filtration to give 0.8 g (7%) of the title compound as an off-white solid.

The synthetic route of 193354-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUGEN, Inc.; US2003/69421; (2003); A1;; ; Patent; Sugen, Inc.; US6051593; (2000); A;,
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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. 59-48-3, name is Indolin-2-one, A new synthetic method of this compound is introduced below., Recommanded Product: 59-48-3

5-Iodo-2-oxindole 2-Oxindole (82.9 g) was suspended in 630 ML of acetic acid with mechanical stirring and the mixture cooled to 10 C. in an ice water bath.. solid N-iodosuccinimide (175 g) was added in portions over 10 minutes.. After the addition was complete the mixture was stirred for 1.0 hour at 10 C. The suspended solid which had always present became very thick at this time.. The solid was collected by vacuum filtration, washed with 100 ML of 50 % acetic acid in water and then with 200 ML of water and sucked dry for 20 minutes in the funnel.. The product was dried under vacuum to give 93.5 g (36%) of 5-iodo-2-oxindole containing about 5% 2-oxindole by proton NMR.

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; Sugen, Inc.; US6350754; (2002); B2;,
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Some common heterocyclic compound, 675109-45-2, name is 6-Amino-2,3-dihydro-1H-isoindol-1-one, molecular formula is C8H8N2O, 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: C8H8N2O

To ethyl acetate (10 mL) was added 6-aminoisoindolin-l-one (100 mg, 0.675 mmol), (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid (179 mg, 0.675 mmol), and DCC (209 mg, 1.012 mmol). The reaction mixture was stirred for 24 h, diluted with ethyl acetate and filtered. The filtrate was washed with 10% citric acid (1 x 10 mL), brine and dried (MgSO4). The crude product was purified by silica gel chromatography (DCM and 0-10%MeOH as eluents) to afford a white foam (0.192 g). The foam was re-dissolved in DCM (5 mL) and to this solution was added TFA (2 mL). After 1 h, the reaction was concentrated to afford 129A (0.29 g, 105%) as a brown oil. LCMS m/z 296.3 [M + H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 675109-45-2, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/157162; (2008); A1;,
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Electric Literature of 611-09-6, The chemical industry reduces the impact on the environment during synthesis 611-09-6, name is 5-Nitroindoline-2,3-dione, I believe this compound will play a more active role in future production and life.

General procedure: Isatin 1 (3 mmol), 0.198 g malononitrile (3 mmol),0.420 g dimedone (3 mmol), and 0.025 g sodium acetate(0.3 mmol) were grinded with the pestle in mortar atambient temperature for 15 min. The resulting mixture wasair dried. Crude solid was then put on filter, rinsed withwater (2 9 2 cm3), and dried with water pump.

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-Nitroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Elinson, Michail N.; Ryzhkov, Fedor V.; Zaimovskaya, Tatiana A.; Egorov, Mikhail P.; Monatshefte fur Chemie; vol. 147; 4; (2016); p. 755 – 760;,
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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. 6941-75-9, name is 5-Bromoisoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Bromoisoindoline-1,3-dione

To a solution of hydroxyproline tripeptide precursor (200 mgs, 0.359mmol) in 4 mL of DMF at room temperature was added 4-bromophthalimide(97 mgs, 0.430 mmol) and triphenyl phosphine (206 mgs, 0.789 mmol).Sonicate until dissolved and add DIAD (152 uL, 0.789 mmol). Stir at roomtemperature overnight. Remove solvent under reduced pressure and extractwith ethyl acetate and water. ‘Separate the layers and dry over MgSCu, filterand strip. Purify using silica gel chromatography eluting (10 -100% ethylacetate in hexane). Further purify on reverse phase HPLC (ACN/Water) toafford 102 as a white solid (98 mgs, 36%). 1H NMR (300 MHz, CDCls): 5 7.95(s, 1H), 7.88 (d, J=7.9 Hz, 1H), 7.71 (d, J= 7.7 Hz, 1H), 7.65 (s, 1H), 7.43 (s, 1H),6.03 (m, 1H), 5.37 (d, J= 15.5 1H), 5.31-5.07 (bs, 5H), 4.91 (m, 1H), 4.77 (m, 1H),4.23-4.03 (bs, 7H), 3.81 (t, J= 7.9Hz, 1H), 2.75 (m, 2H), 2.01 (m, 1H), 1.68-1,50(bs, 8H), 1.30 (q, J= 7.0 Hz, 6H), 1.10 (s, 1H), 0.99 (s, 9H). 31P NMR (300 MHz,CDCls): 8 22.92 (s, IP), 22.75 (s, IP). LC/MS: 766 (M++ 1).

The synthetic route of 6941-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2006/20276; (2006); A2;,
Indoline – Wikipedia,
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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. 17702-83-9, name is 2-(8-Bromooctyl)isoindoline-1,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 17702-83-9

General procedure: 0.91 g (3.6 mmol) N-(2 -bromoethyl) phthalimide was dissolved 20 mL DMF, added 0.53 g (3 mmol)1-benzylpiperazine, 0.62 g (4.5 mmol) K2CO3, heated to 60-70 °C reacted for 4 h, TLC detection, until the benzylpiperazinewas complete reaction. 30 mL of water was added, extracted three times withethyl acetate (20 mL× 3), the organic layer was extracted four times (30mL × 4)with saturated brine, dried with anhydrous magnesium sulfate, and the solventwas distilled off under reduced pressure, cooled to room temperature, silicagel column chromatography (100-200 mesh silica gel, eluent petroleum ether:ethyl acetate = 1:1 – 1: 4) to give 0.7 g (67percent yield) as a white solid. #10;

The synthetic route of 17702-83-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Si, Weijie; Zhang, Tao; Zhang, Lanxiang; Mei, Xiangdong; Dong, Mengya; Zhang, Kaixin; Ning, Jun; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2380 – 2382;,
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