Month: April 2021

Synthetic Route of 15861-23-1, A common heterocyclic compound, 15861-23-1, name is Indoline-5-carbonitrile, molecular formula is C9H8N2, 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 suspension of NaH (2.5 g, 108 mmol) in DMF (100 mL) at 0 C. was added 2,3-dihydro-1H-indole-5-carbonitrile (6.2 g, 43.0 mmol). After 15 min, CS2 (3.8 mL, 64.6 mmol) was added followed by MeI (4.0 mL, 64.6 mmol). The reaction mixture was stirred for 1 h at room temperature. The reaction mixture was then was poured onto ice. The resulting mixture was filtered. The remanence was washed with methylene chloride to give 5-cyano-2,3-dihydroindole-1-carbodithioic acid methyl ester as a off-white solid (7.5 g, 76%). The material was used without further purification.

The synthetic route of 15861-23-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. Lundbeck A/S; US2012/252853; (2012); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

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. 65826-95-1, name is 5-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 65826-95-1

A solution of an HCl salt of Intermediate JB-6 (280 mg, 0.803 mmol) in DCM (2 mL) was added dropwise at 0 C to a stirred solution of sulfurisocyanatidic chloride (0.010 mL, 1.1 mmol) in DCM (3 mL). The reaction mixture was stirred at 0 C for lh and then TEA (0.358 mL, 2.57 mmol) in DCM (1.1 mL) was added and reaction mixture was stirred at 0 C for 3 min. A portion of the crude reaction mixture (-0.8 mL) was added to a stirred solution of 5-methylindoline (32.1 mg, 0.241 mmol) in DCM (1 mL) and the reaction was stirred at rt for 2 h. The reaction mixture was concentrated and partitioned between EtOAc (~2 mL) and 1M HCl (~1 mL) (note: for reactions that followed the procedure outlined here, where there was a basic amine present in the final Example, sat. aq NaHCC was used in the work-up in place of 1 M HC1) and the organic component was washed with brine (1 mL) and concentrated. The residue was dissolved into MeOH, filtered and purified by preparative HPLC to yield the title compound (5.6 mg). LC-MS retention time = 2.88 min; m/z = 551.5 [M+H]+. (Column: Waters BEH C18, 2.0 x 50 mm, 1.7-muiotaeta particles. Solvent A = 95% Water : 5% MeOH : 10 mM NH4OAc. Solvent B = 5% Water : 95% MeOH : 10 mM NH4OAc. Flow Rate = 0.5 mL/min. Start % B = 0. Final % B = 100. Gradient Time = 3 minutes, then a 0.5-minute hold at 100% B. Wavelength = 220). 1H NMR (500 MHz, DMSO-d6) delta 7.24 – 7.04 (m, 4H), 7.00 – 6.66 (m, 8H), 6.21 (br. s., IH), 4.18 (app q, J=7.1 Hz, IH), 4.04 (q, J=7.1 Hz, 2H), 3.94 – 3.82 (m, 2H), 3.58 (d, J=7.0 Hz, IH), 3.49 – 3.39 (m, IH), 2.94 – 2.84 (m, 2H), 2.68 (br. s., IH), 2.47 (dd, J=13.2, 7.3 Hz, IH), 2.21 (s, 3H), 1.35 (t, J=6.8 Hz, 3H), 0.93 (t, J=7.0 Hz, 3H).

The synthetic route of 65826-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BENDER, John A.; GENTLES, Robert G.; PENDRI, Annapurna; WANG, Alan Xiangdong; MEANWELL, Nicholas A.; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; NGUYEN, Van N.; YANG, Zhong; WANG, Gan; KUMARAVEL, Selvakumar; THANGATHIRUPATHY, Srinivasan; BORA, Rajesh Onkardas; HOLEHATTI, Shilpa Maheshwarappa; METTU, Mallikarjuna Rao; PANDA, Manoranjan; (319 pag.)WO2016/172424; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 114041-16-6, These common heterocyclic compound, 114041-16-6, name is 5,6-Dimethoxyisoindoline, 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.

EXAMPLE 67 2-[7-(3,4-Dimethoxyphenyl)-7-[(4-methylphenyl)thio]-heptyl]-1,2,3,4-tetrahydro-6,7,8-trimethoxyisoquinoline The procedure of Example 49 is repeated using 5.31 g 4-[6-bromo-1-[(4-methylphenyl)thio]heptyl]-1,2-dimethoxybenzene, 3.29 g of 5,6-dimethoxyisoindoline and 2.65 g of 6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline. This affords 4.52 g of the desired product as a yellow oil.

The synthetic route of 114041-16-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Powell; Dennis; Paul; Rolf; Hallett; William A.; Berger; Dan M.; Dutia; Minu D.; US5387685; (1995); A;,
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. 107583-37-9, name is 5,6,7-Trifluoroindoline-2,3-dione, A new synthetic method of this compound is introduced below., Application In Synthesis of 5,6,7-Trifluoroindoline-2,3-dione

EXAMPLE 6 5,7-difluoro-6-(4-methylpiperazinyl)isatin STR14 Using the procedure in Example 4 and substituting 5,6,7-trifluoroisatin for 5,6-difluoroisatin gave the title compound in 70% yield.

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; PathoGenesis Corporation; US5441955; (1995); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 3676-85-5,Some common heterocyclic compound, 3676-85-5, name is 5-Aminoisoindoline-1,3-dione, molecular formula is C8H6N2O2, 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.

Preparative Example 1 4-Cyanophthalimide STR16 4-Aminophthalimide (40.0 g) was suspended in 300 ml of water, followed by the addition of 57 ml of concentrated hydrochloric acid. The obtained suspension was stirred under cooling with ice. A solution of 20.6 g of sodium nitrite in 69 ml of water was dropped into the above suspension at a bulk temperature of 5 C. or below. The obtained mixture was cooled to -20 C., followed by the addition of 300 ml of toluene. The resulting mixture was adjusted to pH7 with sodium hydrogencarbonate under vigorous stirring to form a diazonium salt. Separately, a solution of 105.7 g of potassium cyanide in 206 ml of water was dropped into a suspension of 63.4 g of cuprous chloride in 250 ml of water, while the suspension was vigorously stirred under cooling with ice. The obtained mixture was further stirred under cooling with ice for one hour, followed by the addition of 500 ml of ethyl acetate. The diazonium salt prepared above was added into the resulting mixture in several portions and the obtained mixture was stirred under cooling with ice for one hour. The resulting mixture was filtered through Celite to remove insolubles and the Celite was washed with an ethyl acetate/tetrahydrofuran mixture. The filtrates were together left standing to cause liquid-liquid separation. The organic phase was washed with a saturated aqueous solution of sodium hydrogen-carbonate, dilute hydrochloric acid and a saturated aqueous solution of common salt, dried over anhydrous magnesium sulfate and freed from the solvent by vacuum distillation. The title compound (41 g) was obtained as a reddish-brown solid. M.p.: 237.0-238.0 C.; MASS: 173 (MH+); 1H–NMR (400 MHz, DMSO-d6) delta: 8.00(1H, dd, J=7.5, 1.0 Hz), 8.29(1H, dd, J=7.5, 1.5 Hz), 8.36(1H, dd, J=1.5, 1.0 Hz), 11.73(1H, s)

The synthetic route of 3676-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eisai Co., Ltd.; US5849741; (1998); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1035235-27-8, 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. 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of tert-butyl 4-bromoisoindoline-2-carboxylate (1.00 g, 3.37mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1 ,3,2-dioxaborolane) (1.03 g, 4.04 mmol), AcOK (661 mg, 6.74 mmol) and Pd(dppf)C12 (50.0 mg) in dioxane (20 mL) was stirred at 90C lbr 16 h under the nitrogen atmosphere. After cooling down to 20C and LCMS showed the reaction was complete, the mixture was filtered and the filtrate was concentrated under reduced pressure to get the title compound (1.2 g, yield 103%) as a brown solid, which was directly to the next step without further purification ?HNMR(CDC13, 400 MHz) oe 7.69 (d, J 7.2 Hz, 1 H) 7.36-7.27 (m, 2 H) 4.87-4.63 (m, 4 H) 1.52 (s, 9 H) 1.31 (s, 12 H).

The synthetic route of tert-Butyl 4-bromoisoindoline-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KADMON CORPORATION, LLC; KIM, Ji-in; LIU, Kevin; POYUROVSKY, Masha; LU, Dan; ZHU, Zhenping; WO2015/54317; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 6872-06-6, 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. 6872-06-6, name is 2-Methylindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

26.6 mg (0.2 mmol) of 2-methylindoline,81.2 mg of ethyl bromodifluoroacetate (0.4 mmol),2.5 mg (0.02 mmol) of cuprous acetate, 19.1 mg (0.04 mmol) of X-phos, 32.7 mg (0.2 mmol) of cesium carbonate were added to 2 mL of DMF solvent.The reaction was carried out at 110 C for 12 hours, after the reaction was completed, it was cooled, filtered, and the filtrate was evaporated.The solvent was removed and the residue was chromatographed on silica gel.It was washed with a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 8:1.The effluent was collected according to the actual gradient, detected by TLC, and the effluent containing the product was combined.The solvent was distilled off by a rotary evaporator. Vacuum drying to give a yellow liquid 2-methylindoline-1-carbaldehyde19.7 mg, yield 61%.

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

Reference:
Patent; Wenzhou University; Zhang Xiaohong; Li Xiaofang; Zhang Xingguo; (15 pag.)CN108774147; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 24566-79-8, A common heterocyclic compound, 24566-79-8, name is N-(6-Bromohexyl)phthalimide, molecular formula is C14H16BrNO2, 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.

11.9 g tritylsulfide 32 (43.1 mmol, 1.02 eq) were dissolved in 50 mL DMSO. 7.30 mL DBU (48.8 mmol; 1.14 eq) and 13.3 g phthalimide 31 followed by 15 mL DMSO were added. The mixture was stirred for 12 min at ambient temperature. 700 mL ethyl acetate and 200 mL 0.1 N HCl were added. The mixture was stirred until both solvent layers were clear. The layers were separated. The aqueous phase was extracted with ethyl acetate (3x, 50 mL each). The organic solutions were combined, washed with 80 mL sat. NaHC03and 80 mL brine, dried over Na2S04and filtered. The solvent was removed in vacuo. The residue was recrystallized from 240 mL ethanol under heating. The suspension was stored for 1 h at -18C. The trityl protected product 33 was filtered off, washed 2x with ethanol and dried under high vacuum. Yield: 19.6 g; 90 %MS: m/z = 528.07 [M+Na]+

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; ASCENDIS PHARMA A/S; BISEK, Nicola; RAU, Harald; CLEEMANN, Felix; KNAPPE, Thomas; REIMANN, Romy; (140 pag.)WO2016/20373; (2016); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, 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. HPLC of Formula: C10H9NO3

To a suspension of 3.0 g (7.84 mmol) of pyrimidinone A, 4.12 g (15.7 mmol) of triphenylphosphine and 4.12 g (15.7 mmol) of N-(2-hydroxyethyl)-phthalimide in 45 ML of 1,4-dioxane at 5 C. was added dropwise a solution of 2.73 g (2.5 ML, 15.7 mmol) of diethylazodicarboxylate in 10 ML of 1,4-dioxane over a period of 20 min. through an additional funnel.The suspension was stirred at 5 C. for 1 hour and then at room temperature overnight at which point the suspension turned into a yellow solution.The solution was concentrated in vacuo and the residue was purified by column chromatography with silica eluding with 7.5% ethyl acetate in dichloromethane affording 3.92 g of the phthalimide 1 (90% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3891-07-4, its application will become more common.

Reference:
Patent; Goldstein, David Michael; Hawley, Ronald Charles; Lui, Alfred Sui-Ting; Sjogren, Eric Brian; US2003/232847; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

25369-33-9, name is 7-Chloroindolin-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. category: indolines-derivatives

General procedure: To a 25 mL round bottomed flask was added different substituted oxindoles 8 (0.2 mmol, 1.0 equiv.) and bromoethylsulfonium salt 9 (132.99 mg, 0.3 mmol, 1.5 equiv.), DMF (2 mL). The mixture was stirred at room temperature for 5min and Et3N (61.88 mg, 0.6 mmol, 3.0 equiv.) was added into reaction system. The mixture was stirred for 6h at room temperature until the reaction completed, quenched with saturated ammonium chloride solution (5 mL), and was extracted with EtOAc (3¡Á30 mL). The combined organic layer washed with H2O (2¡Á10 mL), dried with anhydrous sodium sulfate. After concentration, product was purified using column chromatography on silica gel with suitable eluent.

The synthetic route of 25369-33-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Qin, Hui; Miao, Yuanyuan; Zhang, Ke; Xu, Jian; Sun, Haopeng; Liu, Wenyuan; Feng, Feng; Qu, Wei; Tetrahedron; vol. 74; 47; (2018); p. 6809 – 6814;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem