Category: 32372-82-0

Reference of 32372-82-0, These common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, 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 solution of 2-chloropyridin-4-amine (0.5 g, 3.90 mmol) in toluene (12 ml) were added isoindoline hydrochloride (0.91 g, 5.85 mmol), BINAP (0.24 g, 0.39 mmol) and potassium tertbutoxide (2.07 g, 9.76 mmol) at rt. The mixture was degassed for 10 mm before addition of Pd2(dba)3 (0.178 g, 0.19 mmol). The reaction mixture was at 110C for 4 hrs. The resulting mixture was poured into cold water (200 ml) and combined with two other batches prepared by an identical method on the same scale. The resulting mixture was extracted with DCM (3 x 100 ml). The organic phase was collected, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (3% MeOH in DCM) yielding 2-(isoindolin-2-yl)pyridin-4- amine (1.2 g, 5.67 mmol). LCMS: Method C, 1.57 mi MS: ES+ 212.29.

The synthetic route of 32372-82-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; KEMP, Mark Ian; STOCKLEY, Martin Lee; MADIN, Andrew; (95 pag.)WO2017/103614; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 32372-82-0,Some common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, molecular formula is C8H10ClN, 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.

Isoindoline hydrochloride (31.1 mg, 0.2 mmol), molybdenum disulfide (4 mg, 0.025 mmol) and a stir bar were placed in a reaction tube. After the inert gas was replaced, 1 ml of DMF was added to seal the reaction tube. . The reaction tube was placed in a 150 C oil bath reaction pot, and the reaction was stirred for 18 hours; after cooling to room temperature, the catalyst was removed by filtration, the filtrate was diluted with 15 mL of water, and extracted with ethyl acetate three times, each time 15 mL; The organic product was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure, and the crude product was subjected to column chromatography with ethyl acetate: petroleum ether = 1:3 (1% triethylamine). Black oil, yield 85%.

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

Reference:
Patent; Xiangtan University; Gong Xing; Xie Guilin; Cai Changqun; Ma Juan; (19 pag.)CN107827817; (2018); A;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, molecular formula is C8H10ClN, 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. Recommanded Product: 32372-82-0

a. 2-chloro-4-(2,3-dihydro-1H-isoindol-2-yl)-pyrimidine A mixture of 0.5 g (3.35 mmol) of 2,4-dichloro-pyrimidine, 0.5 g (3.2 mmol) of 2,3-dihydro-1H-isoindol-hydrochloride and 0.6 ml (3.4 mmol) of N-ethyl-diisopropylamine is stirred in 40 ml dichloromethane for 3 hours. Then the mixture is concentrated by evaporation, the residue is distributed in ethyl acetate/water, the organic phase is separated off and concentrated by evaporation. Yield: 0.4 g (55% of theory), Rf value: 0.4 (silica gel; dichloromethane/ethanol=19:1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 32372-82-0, its application will become more common.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US2003/55263; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

32372-82-0, 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. 32372-82-0, name is Isoindoline hydrochloride, A new synthetic method of this compound is introduced below.

Manganese dioxide (2.80 g, 24.0 mol, 10 eq.) was added to a solution of 93 (550 mg, 2.40 mmol, 1 eq.) in dichloromethane (120 mL) at room temperature. The resulting mixture was stirred at room temperature for 16 h, filtered through a small pad of celite, eluted with ethyl acetate, and concentrated. Solvent was removed to give the corresponding aldehyde, which was used further as obtained. Lithium hydroxide monohydrate (1.02 g, 24.0 mmol) was added to a solution of the aldehyde in methanol (8 mL), tetrahydrofuran (8 mL), and water (8 mL). The resulting mixture was stirred for 14 h at room temperature. The residue was treated with 1 M hydrochloric acid and the pH was adjusted to 2. The resulting suspension was extracted with ethyl acetate (3chi50 mL), and the combined organic layers were washed with saturated sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to afford the corresponding acid as an off-white solid which was used further as obtained. 1-Ethyl- 3-(3- dimethylaminopropyl)carbodiimide (1.53 g, 4.80 mmol) was added to a stirred solution of the acid, isoindoline hydrochloride (485 mg, 3.12 mmol), 1-hydroxybenzotriazole (735 mg, 4.8 mmol), N,N-diisopropylethylamine (1.25 mL, 7.20 mmol) in dichloromethane (24 mL) at 0 C. The resulting solution was stirred at room temperature for 14 h before quenching with a saturated sodium bicarbonate solution (20 mL). The organic layer was washed with 1 M hydrochloric acid solution (15 mL) and saturated sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Si02, 1 :3 hexanes/ethyl acetate) to afford 94 as a light brown amorphous solid (331 mg, 43%). HRMS (ESI+) m/z [M + H+] calc. for C20H2oN03, 322.1443, found 322.1449.

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; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 32372-82-0, name is Isoindoline hydrochloride, 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 32372-82-0, 32372-82-0

General procedure: To a solution of 10 (371 mg, 1.00 mmol) in DMF (5 mL) was added EDC (195 mg, 1.02 mmol), and the resulting mixture was stirred at room temperature for 1 h. Then, to the reaction mixture stirred under ice-cooling was added 12n (192 mg, 1.04 mmol) and N,N-diisopropylethylamine (0.180 mL, 1.06 mmol), and the mixture was stirred at 0 C for 1 h. To the reaction mixture was added 1-(2-aminoethyl)pyrrolidine (0.140 mL, 1.12 mmol), HOBt (174 mg, 1.14 mmol), and EDC (220 mg, 1.15 mmol), and the resulting mixture was stirred at room temperature for 6 h. The reaction mixture was diluted with EtOAc, and the organic layer was washed with H2O, saturated aqueous NaHCO3, and brine, and dried over Na2SO4. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The residue oil was purified by NH silica gel column chromatography (hexane/EtOAc = 50:50 to 0:100) to afford 14n (497 mg, 83%) as a colorless 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, Isoindoline hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Nakao, Akira; Suzuki, Hiroko; Ueno, Hiroaki; Iwasaki, Hiroshi; Setsuta, Tomofumi; Kashima, Akiko; Sunada, Shinji; Bioorganic and Medicinal Chemistry; vol. 23; 15; (2015); p. 4952 – 4969;,
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. 32372-82-0, name is Isoindoline hydrochloride, A new synthetic method of this compound is introduced below., 32372-82-0

1-Ethyl-3-(3- dimethylaminopropyl)carbodiimide (2 eq.) was added to a stirred solution of 7 (1 eq.), isoindoline hydrochloride (1.5 eq.), 1-hydroxybenzotriazole (2 eq.) N,N- diisopropylethylamine (2 eq.) in dichloromethane (150 mL) at 0 C. The resulting solution was stirred at room temperature for 14 h before quenching with saturated sodium bicarbonate solution (120 mL). The organic layer was washed with 1 M hydrochloric acid solution (120 mL) and saturated sodium chloride solution (120 mL), dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography (Si02, 1 :4 hexanes/ethyl acetate) to afford 8 (82%) as a white amorphous solid. 1H- NMR (400 MHz, CDC13) delta 7.97 (m, 1H), 7.43 (m, 2H), 7.37 (m, 2H), 6.07 (s, 2H), 6.00 (s, 2H), 4.52 (s, 2H), 4.41 (s, 2H), 3.35 (s, 3H), 3.27 (s, 3H), 3.05 (m, 1H), 1.14 (d, J=7.52, 6H).13C- NMR (100 MHz, CDC13) delta 169.5,157.5, 156.6, 140.0 (2), 130.6, 128.5 (2), 126.2 (2), 126.0, 111.2, 99.9, 95.2, 94.5, 56.1, 55.6 (2), 26.9, 23.6 (2).

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; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

A common heterocyclic compound, 32372-82-0, name is Isoindoline hydrochloride, molecular formula is C8H10ClN, 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. 32372-82-0.

1-Ethyl-3- (3-dimethylaminopropyl)carbodiimide (1.63 g, 8.54 mmol, 2.0 eq.) was added to a stirred solution of S14 (950 mg, 4.27 mmol, 1 eq.), isoindoline hydrochloride (731 mg, 4.70 mmol, 1.1 eq.), 1-hydroxybenzotriazole (635 mg, 4.70 mmol, 1.1 eq.) N-,N-diisopropylethylamine (3.26 mL, 18.8 mmol, 4.4 eq.) in dichloromethane 42 mL) at 0 C. The resulting solution was stirred at rt for 14 h before quenching with saturated sodium bicarbonate solution (30 mL). The organic layer was washed with 1 M hydrochloric acid solution (30 mL) and saturated sodium chloride solution (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (Si02, 3 : 10 hexanes/ethylacetate) to afford S15 (1.22 g, 91.8%) as a white amorphous solid. 1H NMR (400 MHz, CDC13) delta 10.47 (s, 1H), 7.48 – 7.21 (m, 5H), 7.15 (d, J= 7.4 Hz, 1H), 5.01 (s, 2H), 4.58 (s, 2H), 4.02 – 3.76 (m, 4H), 1.32 (d, J= 6.8 Hz, 7H).13C NMR (100 MHz, CDC13) delta 190.8, 167.6, 153.7, 144.9, 136.4, 136.4, 134.4, 132.5, 128.0, 127.7, 126.1, 123.3, 122.7, 111.2, 56.1, 53.4, 52.3, 27.3, 24.4 (2). HRMS (ESI+) m/z [M + Na+] calcd for C20H21NO3Na, 346.1419, found 346.1404.

The synthetic route of Isoindoline hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem