Category: 41910-64-9

Reference of 41910-64-9, These common heterocyclic compound, 41910-64-9, name is 4-Chloroindoline, 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 6 4-(4-Chloro-2,3-dihydro-indol-1-yl)-6,7-dimethoxy-quinazoline Utilizing a procedure analogous to that described in Example 2, this product was prepared in 92% yield from 4-chloro-indoline (2 eq.) and 4-chloro-6,7-dimethoxy-quinazoline (1.0 eq) in i-PrOH. (M.P. 172-179 C. (dec); LC-MS: 342 (MH+); anal. RP18-HPLC RT: 4.60 min.).

The synthetic route of 41910-64-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US5736534; (1998); 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. 41910-64-9, name is 4-Chloroindoline, A new synthetic method of this compound is introduced below., Product Details of 41910-64-9

A suspension of 4-chloroindoline (1.00 g) and D-galactose (1.94 g) in H2O (3.0 ml)-ethyl alcohol (20 ml) was refluxed for 29 hours under argon atmosphere. The solvent was evaporated under reduced pressure to give crude 4-chloro-1-(beta-D-galactopyranosyl)indoline, which was used in the subsequent step without further purification.

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; Tanabe Seiyaku Co., Ltd.; US2008/27014; (2008); 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. 41910-64-9, name is 4-Chloroindoline, A new synthetic method of this compound is introduced below., Computed Properties of C8H8ClN

Step 2: (cis) (4-(4-chloroindolin- l-yl)thiazol-2-yl) (2,6-dimethylmorpholino) methanone (cis) (4-bromothiazol-2-yl) (2,6-dimethylmorpholino)methanone (step- 1 of compound 45, 1.0 g, 3.28 mmol) and 4-chloroindoline (0.55 g, 3.60 mmol) were added to seal tube containing toluene (25 ml). Sodium tert-butoxide (0.47 g, 4.91 mmol) was added, the nitrogen gas was bubbled through reaction mixture for 15 minutes and tris(dibenzylideneacetone)dipalladium(0) (0.15 g, 0.16 mmol) was added under nitrogen and the tube was sealed. The reaction mixture was heated at 100C for 18 hr under stirring. The progress of reaction was monitored by TLC. The reaction mixture was cooled to 25C and diluted with ethyl acetate (100 ml) and washed with water (25 ml). The organic layer was dried over sodium sulfate filtered and concentrated under reduced pressure to obtain a crude product; which was purified by flash column chromatography using 15% ethyl acetate in hexanes as an eluent to obtain the title compound (0.75 g, 60.6%). MS: m/z 378 (M+l). iHNMR (CDCI3, 400 MHz): delta 7.52 (d, J = 8.8 Hz, 1H), 7.18-7.05 (m, 2H), 6.33 (s, 1H), 5.56 (d, J = 13.2 Hz, 1H), 4.56 (d, J = 13.2 Hz, 1H), 3.99 (t, J = 8.8 Hz, 2H), 3.82-3.66 (m, 2H), 3.24 (t, J = 8.8 Hz, 2H), 3.10 (t, J = 12.8 Hz, 1H), 2.63 (t, J = 12.8 Hz, 1H), 1.41- 1.22 (m, 6H).

The synthetic route of 41910-64-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LUPIN LIMITED; SINHA, Neelima; KARCHE, Navnath, Popat; HAJARE, Anil, Kashiram; ADURKAR, Shridhar, Keshav; LAIRIKYENGBAM, Bikramjit, Singh; RAJE, Firoj, Aftab; TILEKAR, Ajay, Ramchandra; THUBE, Baban, Rupaji; PALLE, Venkata P.; KAMBOJ, Rajender, Kumar; WO2013/132380; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 41910-64-9, name is 4-Chloroindoline, 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 41910-64-9, Safety of 4-Chloroindoline

1 , 1 -dime th yleth yl 4-chloro-2, 3-dih ydro- 1 H-indole- 1 -carboxylateA solution of 4-chloro-2,3-dihydro-1 H-indole (4.0 g, 26.0 mmol), Boc20 (6.05 mL, 26.0 mmol), DIEA (9.10 mL, 52.1 mmol), DMAP (0.318 g, 2.60 mmol) was stirred at room temperature overnight. LCMS indicated complete conversion. The reaction mixture was poured into 0.1 N HCI (10 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organics were dried over sodium sulfate, filtered and concentrated to afford 1 ,1 – dimethylethyl 4-chloro-2,3-dihydro-1 H-indole-1 -carboxylate (6.36 g) as a yellow oily semisolid. LC-MS(ES) m/z = 198 [M+H-t-Bu]+. 1H NMR (400 MHz, DMSO-d6) delta ppm 1 .51 (s, 9 H), 3.07 (t, J=8.72 Hz, 2 H), 3.95 (t, J=8.72 Hz, 2 H), 6.98 (d, J=8.84 Hz, 1 H), 7.19 (t, J=8.08 Hz, 1 H), 7.48 – 7.70 (m, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloroindoline, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE LLC; AXTEN, Jeffrey, Michael; GRANT, Seth, Wilson; HEERDING, Dirk, A.; MEDINA, Jesus, Raul; ROMERIL, Stuart, Paul; TANG, Jun; WO2011/119663; (2011); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 41910-64-9, 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. 41910-64-9, name is 4-Chloroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A solution of an HCl salt of Intermediate JB-2 (35 mg, 0.11 mmol) in DCE (0.50 mL) was slowly added to a stirred solution of sulfurisocyanatidic chloride (0.014 mL, 0.16 mmol) in DCE (0.25 mL) at 0C and the reaction mixture was allowed to stir at 0C for 1 h. The reaction mixture was treated with a solution of TEA (0.049 mL, 0.35 mmol) in DCE (0.25 mL), stirred at 0C for 5 minutes and then added to a solution of 4- chloroindoline (33.5 mg, 0.218 mmol) in DCE (0.25 mL). The reaction was sealed, shaken at rt for 2h, concentrated and then purified by preparative HPLC to yield the title compound. LC-MS retention time = 2.70 min; m/z = 543.2 [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 7.30 – 7.25 (m, 1H), 7.16 – 7.07 (m, 5H), 7.02 – 6.98 (m, 2H), 6.96 – 6.92 (m, 2H), 6.71 (d, J=7.3 Hz, 2H), 6.59 (d, J=8.4 Hz, 1H), 4.31 – 4.25 (m, 1H), 4.20 – 4.13 (m, 1H), 4.12 – 4.06 (m, 1H), 3.79 (s, 3H), 3.07 (s, 3H), 3.07 – 3.01 (m, 2H), 2.74 – 2.69 (m, 1H), 2.44 (dd, J=13.6, 7.7 Hz, 1H).

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, 4-Chloroindoline, other downstream synthetic routes, hurry up and to see.

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

Related Products of 41910-64-9, 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. 41910-64-9, name is 4-Chloroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Step 2d: 2 ml of toluene, 90 mg of ethyl (1-cyclopropyl-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate and, finally, dropwise, 0.55 ml of a 2M solution of trimethylaluminum in toluene are successively added to a solution of 113 mg of 4-chloroindoline in 4 ml of tetrahydrofuran. The reaction mixture is heated at 90 C. for 4 hours, and then cooled to ambient temperature, and 5 ml of methanol are added. After the addition of 10 g of silica, the reaction mixture is concentrated under reduced pressure. After purification by silica column chromatography (solid deposit), elution being carried out with a mixture of dichloromethane and methanol (100/0 then 98/02 V/V), 39 mg of 2-[2-(4-chloro-2,3-dihydro-1H-indol-1-yl)-2-oxoethyl]-3-cyclopropyl-6-(morpholin-4-yl)pyrimidin-4(3H)-one are obtained in the form of a white solid, the characteristics of which are the following:1H NMR spectrum (400 MHz): 0.83 (m, 2H); 1.07 (m, 2H); 2.69 (m, 1H); 3.18 (t, J=8.6 Hz, 2H); 3.36 (m, 4H); 3.55 (m, 4H); 4.18 (s, 2H); 4.23 (t, J=8.6 Hz, 2H); 5.27 (s, 1H); 7.09 (d, J=8.1 Hz, 1H); 7.21 (t, J=8.1 Hz, 1H); 7.98 (d, J=7.9 Hz, 1H)Mass spectrometry: method ARetention time Tr (min)=0.85;[M+H]+: m/z 415; [M-H]-: m/z 413

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, 4-Chloroindoline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI; Brollo, Maurice; Carry, Jean-Christophe; Certal, Victor; Didier, Eric; Doerflinger, Gilles; EL Ahmad, Youssef; Filoche-Romme, Bruno; Halley, Frank; Karlsson, Karl Andreas; Schio, Laurent; Thompson, Fabienne; US2013/274253; (2013); A1;,
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. 41910-64-9, name is 4-Chloroindoline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H8ClN

A ImL {2-[4-({[(2,5-dioxopyrrolidin-l-yl)oxy]carbonyl}amino)-2- (l-methyl-lH-pyrazol-5-yl)phenoxy]ethyl}carbamate in dimethylformamide (78.8 mumol) was added to 4-chloroindoline (14.52mg, 1.2eq) and stirred at room temperature for 18hr. To this was added 2.0M hydrochloric acid in ether (197 muL, 5eq) and the reaction was stirred at room temperature for 24hr (2-3 drops of concentrated hydrochloric acid was added if the deprotection was incomplete and the resulting mixture was stirred for another 24hr). The ether and hydrochloric acid were evaporated under a stream of nitrogen and the resulting material was purified by etaPLC. The proper fractions were collected and lyophilized to afford the title compound as a white solid in 43.5% yield. LCMS m/z (%) = 412 (M+eta 35Cl, 100), 414 (M+eta 37Cl, 36). 1H NMR (400 MHz, DMSO-4) delta ppm 3.10 – 3.24 (m, 4 H), 3.71 (s, 3 H), 4.13 – 4.21 (m, 4 H), 6.34 (d, /=2.02 Hz, 1 H), 6.96 (d, /=8.08 Hz, 1 H), 7.13 – 7.21 (m, 2 H), 7.48 – 7.50 (m, 2 H), 7.64 (dd, /=8.84, 2.78 Hz, 1 H), 7.81 (d, /=7.58 Hz, 1 H), 7.92 (s, 2 H), 8.63 (s, 1 H).

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 41910-64-9.

Reference:
Patent; ARENA PHARMACEUTICALS, INC.; WO2007/136703; (2007); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

41910-64-9, name is 4-Chloroindoline, 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. Quality Control of 4-Chloroindoline

A mixture of 4-chloroindoline (2.88 g) and D-glucose (3.38 g) in ethyl alcohol (150 ml)-H2O (10 ml) was refluxed under argon atmosphere overnight. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=100:0-88:12) to give 4-chloro-1-(beta-D-glucopyranosyl)indoline (3.35 g) as a colorless foam. APCI-Mass m/Z 316/318 (M+H). 1H-NMR (DMSO-d6) delta 2.87-3.02 (m, 2H), 3.07-3.12 (m, 1H), 3.20-3.32 (m, 2H), 3.38-3.47 (m, 2H), 3.51-3.60 (m, 2H), 3.68-3.73 (m, 1H), 4.34-4.37 (m, 1H), 4.63 (d, J=8.3-Hz, 1H), 4.93 (d, J=5.1 Hz, 1H), 5.03 (d, J=4.0 Hz, 1H), 5.06 (d, J=4.5 Hz, 1H), 6.53 (d, J=8.0 Hz, 1H), 6.60 (d, J=8.0 Hz, 1H), 6.99 (t, J=7.9 Hz, 1H).

The synthetic route of 41910-64-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tanabe Seiyaku Co., Ltd.; US2008/27122; (2008); 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 41910-64-9 as follows. Recommanded Product: 41910-64-9

General procedure: To the appropriate cyclic amine (20 mmol) in hexane (15 mL) amyl nitrite (60 mmol, 7 g, 8 mL) was added in one portion. The resulting mixture was stirred for 30 min at room temperature. The precipitated solid was collected by filtration, washed with hexane, dried and used for preparation of corresponding N-aminoindolines 3a-d and N-amino-1,2,3,4-tertahydroquinolines 7a,b without purification.

According to the analysis of related databases, 41910-64-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; S?czewski, Franciszek; Wasilewska, Aleksandra; Hudson, Alan L.; Ferdousi, Mehnaz; Rybczy?ska, Apolonia; Boblewski, Konrad; Lehmann, Artur; Acta poloniae pharmaceutica; vol. 72; 2; (2015); p. 277 – 287;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 41910-64-9, 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. 41910-64-9, name is 4-Chloroindoline belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Initially a 2.5 dram reaction vial was charged with 60% sodium hydride (0.028 g, 0.700 mmol) and salicylamide (0.072 g, 0.525 mmol) in DMF (2 mL).The mixture was allowed to stir at room temperature for 1 hour.4-Chloro-6-ethoxy-2- (pyridin-3-yl) quinazoline (0.100 g, 0.350 mmol) was then added to the mixture and the reaction was allowed to proceed overnight at room temperature.LC-MS analysis of the crude mixture showed that the formed product was about 85% and 10% remained as starting material. Water (30 mL) was added to the mixture and the product was extracted with chloroform (3 × 15 mL). The combined organic layers were dried (Na 2 SO 4), filtered and concentrated. The crude product was purified by ISCO (silica gel, 97.5: 2.5 CH2 Cl2 / MeOH; 12 g column) to afford 13.9 mg of the desired product as a white solid (10.3%).

The synthetic route of 4-Chloroindoline has been constantly updated, and we look forward to future research findings.