Indolines-derivatives

923590-95-8, name is 4-Bromoisoindoline hydrochloride, 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. Safety of 4-Bromoisoindoline hydrochloride

To a solution of (2S,4R)-BOC-4-hydroxyproline methyl ester (126.3 g,515 mmol) in DMF (960 mL) at 00C was added N,N’-carbonyldiimidazole (83.51 g, 515 mmol). The reaction mixture was stirred at RT for 3 hours. 4-Bromoisoindoline hydrochloride (12O g, 515 mmol) and DIPEA (96.3 mL, 540 mmol) were added, and the reaction mixture heated to 50C for 6 hours. The reaction mixture was then allowed to cool to RT and stirred overnight. The reaction mixture was partitioned between EtOAc (3 L) and 10% aqueous KHSO4 (6 L), the aqueous re-extracted with EtOAc (2 L) and the combined organic phases washed with 10% aqueous NaHCO3, brine, dried over Na2SO4 and solvent evaporated to a foam (239 g). LRMS (ESI) m/z 471.0 [(M+H)+; calcd for C20H26BrN2O6: 471.1].

The synthetic route of 923590-95-8 has been constantly updated, and we look forward to future research findings.

Electric Literature of 959235-95-1,Some common heterocyclic compound, 959235-95-1, name is 6-(Trifluoromethoxy)indoline, molecular formula is C9H8F3NO, 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.

HATU (7.02 g, 18.46 mmol) was added to a mixture of 6-(trifluoromethoxy)indoline [CAS 959235-95-1 ] (2.5 g, 12.3 mmol), 2-(4-chloro-2-fluorophenyl)acetic acid [CAS 194240-75-0] (2.32 g, 12.3 mmol) and diisopropylethylamine (6.1 ml_, 36.9 mmol) in DMF (100 ml_). The resulting mixture was stirred at room temperature for 12 h. The mixture was diluted with water, the precipitate was filtered off, and washed with water. The residue was taken up with EtOAc and the organic solution was washed with a 10% aqueous solution of K2CO3, brine, dried over MgSO , filtered and the solvent was evaporated under reduced pressure. The residue product was crystallized from diisopropyl ether to give 2-(4-chloro-2- fluorophenyl)-1 -(6-(trifluoromethoxy)indolin-1 -yl)ethanone 10a (4 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-(Trifluoromethoxy)indoline, its application will become more common.

Reference of 35197-64-9, 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 35197-64-9 as follows.

4-(4,6-d4-(4,6-Dimethoxy-l,3,5-triazin-2-yl)-4-methylmo holin-4-ium chloride (166 mg, 0.598 mmol) was added to a solution of methyl 3-amino-4-hydroxybenzoate (100 mg, 0.598 mmol) and 2-bromo-4-(l,3-dioxoisoindolin-2-yl)butanoic acid (187 mg, 0.598 mmol) in DMF (5 mL), and the reaction stirred overnight at ambient temperature. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was separated and concentrated to afford methyl 3-(2-bromo-4-(l,3-dioxoisoindolin-2-yl)butanamido)-4-hydroxybenzoate as a thin film which was used directly in the next step without further purification. MS (ESI, m/z): 461, 463 [M+H]+.

According to the analysis of related databases, 35197-64-9, the application of this compound in the production field has become more and more popular.

Reference of 3484-35-3, 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. 3484-35-3, name is 5-Methylindolin-2-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

3-Methylindole-2-carbaldehyde was prepared as described in the literature: 1) David W. M. Benzies, Pilar Matinez Fresneda and R. Alan Jones, Synthetic Communications, 16 (14), 1799-1807 (1986) and 2) Chatterjee, A. and Biswas, K. M., J. Org. Chem., 1973, 38,4002. A mixture of 5-methyl-2-oxindole (59 mg), 3-methylindole-2-carbaldehyde (56 mg) and piperidine (30 mg) in ethanol (1 mL) was heated in a sealed tube at 90 C. for overnight. The mixture was cooled to room temperature. The solid was collected by vacuum filtration, washed with cold ethanol and dried in a vacuum oven for overnight to give 72 mg (74% yield) of 5-methyl-3-(3-methyl-1H-indol-2-ylmethylene)-1,3-dihydro-indol-2-one. 1H NMR (360 MHz, DMSO-d6) 13.03 (s, br, 1H, NH), 10.88 (s, br, 1H, NH), 7.84 (s, 1H, vinyl), 7.71 (s, br, 1H), 6.62 (d, J=8 Hz, 1H), 7.48 (d, J=8 Hz, 7.26 (t, J=7 Hz, 1H), 7.06 (t, J=7 Hz, 1H), 7.0 (d, J=8 Hz, 1H), 6.78 (d, J=8 Hz, 1H), 2.59 (s, 3H, CH3), 2.32 (s, 3H, CH3). MS m/z 289 [M+1]+.

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

Reference of 5181-35-1, 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 5181-35-1 as follows.

To a mixture of 2-(2-bromoetho xy)isoindo line- 1,3- dione (20 g, 74 mmol, prepared according to the procedure described in step 1 of preparation 10) and 2H-tetrazole-5-carboxylic acid ethyl ester (10.51 g, 74 mmol) in dimethylformamide (100 ml) was added cesium carbonate (24.13 g, 74 mmol) lot wise under stirring at room temperature. After 16 hours, the reaction mixture was filtered through filter paper and filtrate was slowly poured into chilled water (700 ml) under stirring. After 30 minutes of stirring, the product was extracted with ethyl acetate (200 ml and 100 ml). The combined organic layers were washed with brine (100 ml). The organic extract was dried over anhydrous sodium sulfate and concentrated in vacuo to yield 12.5 g of the titled compound. The compound was purified by column chromatography using mixture of acetone and hexane as an eluent. The fractions containing the compound were collected and concentrated to provide 10 g of mixture of ethyl l-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2- yl)oxy]ethyl}- lH-tetrazole-5-carboxylate and ethyl 2-{2-[(l,3-dioxo- l,3-dihydro-2H-isoindol-2- yl)oxy]ethyl}-2H-tetrazole-5-carboxylate in 53% yield Analysis: Mass: 332(M+1); for Molecular weight: 331 and for Molecular formula: C14H13N5O5

According to the analysis of related databases, 5181-35-1, the application of this compound in the production field has become more and more popular.

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., Computed Properties of C8H4N2O4

General procedure: A mixture of isatin (1 mmol), reactive methylene compound(1 mmol) and 1,3-dicarbonyl compound (1 mmol)in the presence of [Sipim]Cl (0.05 g) in water (5 mL)was refluxed with stirring in an oil bath. The progress ofthe reaction was monitored by TLC. After completion ofthe reaction, the mixture was filtered and remaining waswashed with warm ethanol (3 × 10 mL) in order to separate[Sipim]Cl catalyst. After cooling the ethanol phase, theprecipitates were filtered. The crude products were purifiedby recrystallization from ethanol (95 %).

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

Electric Literature of 102359-00-2, 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 102359-00-2 as follows.

Compound 1 (177g, 1 mmol), iodomethane (426 mg, 3 mmol), and NaH (60%, 160 mg, 4 mmol) were combined in THF (5 ml_). The reaction mixture was stirred at 60 C for 3 h. The mixture was concentrated to get a residue The crude residue was dissolved in Py (5 ml_). tert-Butyl 2-amino-4-(thiophen-2-yl)phenylcarbamate (290 mg, 1 mmol) and EDCI (382 mg, 2 mmol) were added and the reaction was stirred at rt overnight. The mixture was concentrated to get a residue, which was purified by silica gel to get compound 2 (246 mg, 50%, 2 steps) as yellow solid.

According to the analysis of related databases, 102359-00-2, the application of this compound in the production field has become more and more popular.

Application of 3485-84-5, 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. 3485-84-5, name is N-Vinylphthalimide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: In a sealed tube under argon atmosphere, were introducedcompound 4 (4.74 g, 20 mmol), DMF (20 mL), triethylamine(11.16 mL, 80 mmol), palladium diacetate (225 mg, 1 mmol), tri(otolyl)-phosphine (609 mg, 2 mmol) and N-vinylphthalimide (5.20 g,30 mmol). The mixturewas stirred at 110 C for 3 h and hydrolyzed.The formed solid was solubilized in CH2Cl2, washed with water andbrine, dried over MgSO4 and evaporated under reduced pressure.The crude productwas recrystallized from acetonitrile to afford 7 asa white solid (91% yield); Mp 199-200 C; 1H NMR (300 MHz,CDCl3):delta 8.49 (d, 1H, 15 Hz), 8.25 (d, 1H, 15 Hz), 8.00 (d, 1H, 9.0 Hz),7.92 (m, 2H), 7.81 (d, 1H, 7.8 Hz), 7.76 (m, 2H), 7.65 (d, 1H, 7.8 Hz),7.38 (t, 1H, 7.8 Hz), 6.96 (d, 1H, 9.0 Hz), 4.23 (s, 3H); IR (upsilon, cm-1, KBr):1715 (C=O); MS (APCI, pos. 30 V) m/z: [M+H]+, 331.34. HRMS(ESI+): m/z = calcd. for C20H15N2O3 [M+H]+ 331.10772 found:331.10606.

The synthetic route of N-Vinylphthalimide has been constantly updated, and we look forward to future research findings.

Related Products of 552330-86-6, These common heterocyclic compound, 552330-86-6, name is 5-Bromoisoindolin-1-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.

5-Bromo-2,3-dihydro-isoindol-l-one (leq) was added to a solution of benzyl bromide (l . l eq) and K2CO3 (2eq) in DMF under N2. The mixture was stirred at rt for 16 hrs. Reaction was diluted in water and the compound precipitated. The solid was filtered and dried under reduced pressure. Compound was used in the next step without further purification.

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

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. 667463-64-1, name is 6-Bromo-1-methylindoline-2,3-dione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 6-Bromo-1-methylindoline-2,3-dione

I-3.1 (397 mg, 1.65 mmol) and hydrazine hydrate (1 mL, 20.6 mmol) are heated to 100 C. for 1 h and at 125 C. for 1 h. To the cool reaction mixture DCM and water are added and the aqueous layer extracted twice with DCM. The combined organic layers are washed with brine, dried, concentrated and the residue purified via column chromatography (using solvent mixture cyclohexane/EA=3:1). Yield 65%. m/z 226 [M+H]+, m/z 224 [M+H]-, rt 0.58 min, LC-MS Method b.

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 667463-64-1.