Tag: M.W=100-200

Synthetic Route of 32372-82-0, 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. 32372-82-0, name is Isoindoline hydrochloride belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

1-Ethyl-3-(3- dimethylaminopropyl)carbodiimide (5.20 g, 27.64 mmol, 2 eq.) was added to a stirred solution of 83 (3.0 g, 13.82 mmol, 1 eq.), isoindoline hydrochloride (3.22 g, 20.73 mmol, 1.5 eq.), 1- hydroxybenzotriazole (3.73 g, 27.64 mmol, 2 eq.) N,N-diisopropylethylamine (4.81 mL, 27.64 mmol, 2 eq.) in dichloromethane (150 mL) at 0 C. The resulting solution was stirred at rt 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 84 (3.24 g,77.9 %) as a white amorphous solid. 1H NMR (400 MHz, CDC13) delta 10.92 (s, 1H), 7.73 (d, J= 2.2 Hz, 1H), 7.48 (dd, J= 8.8, 2.4 Hz, 1H), 7.34 (s, 4H), 6.94 (d, J= 8.8 Hz, 1H), 5.10 (s, 4H).13C NMR (100MHz, CDCI3) delta 169.4, 159.4, 136.1 (2), 134.8, 130.5, 128.2 (2), 122.8 (2), 120.2, 118.7 110.2, 55.8, 53.3. HRMS (ESI+) m/z [M + H+] calcd for C15H13BrN02, 318.0130, found 318.0119.

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:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
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Electric Literature of 71294-03-6,Some common heterocyclic compound, 71294-03-6, name is 7-Fluoroindolin-2-one, molecular formula is C8H6FNO, 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.

40 g of 7-fluoroanthraquinone was added to 450 ml of anhydrous methylene chloride, 15 g of aluminum trichloride was added, 60 g of oxalyl chloride was added, the mixture was heated to reflux for 2 hours, cooled to room temperature, and then water was added thereto for liquid separation, drying, and concentration. The residue was columned to give 47 g of 2-(7-fluoro-1H-indol-3-yl)-2-oxoacetyl chloride.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Fluoroindolin-2-one, its application will become more common.

Reference:
Patent; Hunan Huateng Pharmaceutical Co., Ltd.; Cheng Jia; (6 pag.)CN107698483; (2018); A;,
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Application of 1074-82-4, 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. 1074-82-4, name is Potassium 1,3-dioxoisoindolin-2-ide belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Into a reaction vessel were put potassium phthalimide (5.00g, 27.0mmol), benzyltrimethylammonium chloride (0.50g, 2.70mmol) and DMF (50ml) and then thereto was added (R)-epichlorohydrin (5.00g, 54.0mmol). The mixture was stirred at room temperature for 16 hours and the solvent was removed. To the residue was added ethyl acetate (30ml), the mixture was washed with water (20ml) and ethyl acetate was removed to give crude (R)-glycidylphthalimide (4.48g, yield: 82%, optical purity: 63%e.e.) as a white 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, Potassium 1,3-dioxoisoindolin-2-ide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DAISO CO., LTD.; EP1403267; (2004); A1;,
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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. 317-20-4, name is 7-Fluoroisatin, A new synthetic method of this compound is introduced below., Product Details of 317-20-4

General procedure: In 25 ml a round bottom flask with minimum amount of water as solvent at 80 C, to this add o-phenylenediamine (1 mmol), tetronic acid (1 mmol), isatin (1 mmol) and sulphamic acid (4 mol %) it was stirred, refluxed at 100 C for 3 h. The progress of reaction was monitored by TLC. After completion of the reaction, ice-cold water was added and stirred for 5 min. The precipitated solid collected by filtration, washed with water and recrystallised using ethanol.

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:
Article; Nagaraju, Burri; Kovvuri, Jeshma; Babu, K. Suresh; Adiyala, Praveen Reddy; Nayak, V. Lakshma; Alarifi, Abdullah; Kamal, Ahmed; Tetrahedron; vol. 73; 49; (2017); p. 6969 – 6976;,
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Related Products of 1127-59-9, 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. 1127-59-9, name is 7-Methylindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

8-Methyl-2-(2-pyridyl)quinoline-4-carboxylic acid (VI; R1 =2′-aza, R2 =H) A mixture of 2-acetylpyridine (IV; R1 =2-aza: 6.05 g, 0.05 mol) and 7-methylisatin (V; R2 =H: 8.52 g, 0.053 mol) in 65 mL of 50percent EtOH–H2 O containing KOH (13 g) was refluxed for 2 h, then diluted with 50percent EtOH–H2 O to obtain a homogeneous solution, filtered and acidified (HOAc). The resulting acid was collected, washed with 30percent EtOH–H2 O and recrystallized from DMF–EtOH to provide the product (9.4 g, 67percent, mp. 319°-320° C. Anal. (C16 H12 N2 O2) C,H,N. Similar reactions using appropriately substituted acetophenones gave the 8-methyl-2-phenylquinoline-4-carboxylic acids (VI) listed in Table III.

The synthetic route of 7-Methylindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Development Finance Corporation of New Zeland; US4904659; (1990); A;,
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Reference of 61-70-1, These common heterocyclic compound, 61-70-1, name is 1-Methylindolin-2-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.

General procedure: All reactions were conducted in 10 mL glass vials fitted with crimpcap septum caps. The reaction vial, equipped with a magnetic stir bar,was charged under an N2 atmosphere with 1-methylindolin-2-one (4)(73.6 mg, 0.5 mmol), Pd2(dba)3 (10 mg, 0.011 mmol, 2.5 mol%), i-Pr-BI-DIME (7) (0.022 mmol, 5 mol%), LiHMDS (1 M in toluene, 0.55 mL,0.55 mmol) and the aryl halide (1.1 equiv), then sealed with a crimpcap septum. THF (0.5 mL) and toluene (0.5 mL) were added via syringe and the reaction was heated to 70 C for 4-24 h. The reaction mixture was cooled to room temperature then filtered through a Celite pad with EtOAc (5 mL) as eluent. The filtered solution waswashed with H2O (3 mL), dried over MgSO4 and then concentrated under reduced pressure. The crude residue was purified using a 12 g silica column (30% EtOAc/hexanes) to afford the corresponding oxindole product.

Statistics shows that 1-Methylindolin-2-one is playing an increasingly important role. we look forward to future research findings about 61-70-1.

Reference:
Article; Mangunuru, Hari P. R.; Malapit, Christian A.; Haddad, Nizar; Reeves, Jonathan T.; Qu, Bo; Rodriguez, Sonia; Lee, Heewon; Yee, Nathan K.; Song, Jinhua J.; Busacca, Carl A.; Senanayake, Chris H.; Synthesis; vol. 50; 22; (2018); p. 4435 – 4443;,
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Electric Literature of 14389-06-1,Some common heterocyclic compound, 14389-06-1, name is 5-Chloro-7-methylindoline-2,3-dione, molecular formula is C9H6ClNO2, 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.

Reference Example 23 Synthesis of 2-phenyl-6-chloro-8-methylquinoline-4-carboxylic Acid The above-mentioned compound (1.03 g) was formed from 1.95 g of 5-chloro-7-methylisatin and 2.40 g of acetophenone in the same manner as in Reference Example 1. 1 H-NMR(DMSO-d6), delta: 2.53(s, 3H), 7.55(m, 3H), 7.65(d, 1H), 8.03(d, 1H), 8.25(d, 2H), 8.35(s, 1H), 8.46(s, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Chloro-7-methylindoline-2,3-dione, its application will become more common.

Reference:
Patent; Mitsui Toatsu Chemicals, Inc.; US5627193; (1997); A;,
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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. 39755-95-8, name is 5-Methoxyisatin belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 5-Methoxyisatin

General procedure: A mixture of isatin derivatves (1 mmole), malononitrile (1 mmole),1,3-dicarbonyl compounds (1 mmole), and Fe3+-mont. (0.05 g) in CH3CN(5 mL) was heated using an Elmasonic S 40 H ultrasonic cleaning unit at 50 C under silent condition. The progress of the reaction was monitored by TLC (EtOAc/hexane 3:7). After completion of the reaction, the catalyst was removed by filtration. Water was added to the residue. The solid which was obtained was filtered off and dried to provide pure products of the spirooxindole derivatives (4a-j) (Table 3).

The synthetic route of 39755-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mamaghani, Manouchehr; Tabatabaeian, Khalil; Pourshiva, Mina; Nia, Roghayeh Hossein; Journal of Chemical Research; vol. 39; 6; (2015); p. 314 – 317;,
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2913-97-5, name is N-(2-Oxoethyl)phthalimide, 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. Product Details of 2913-97-5

Under a nitrogen atmosphere, to a mixture of NaH (560 mg, 22 mmol) and anhydrous THF (90 mL), a solution of diethyle(2-oxopropyl)phosphonate (4.27 g, 22 mmol) in THF (60 mL) was added over 10 min. The resulting solution was stirred at r.t. for 1 h. Then Compound 2 (6.24 g, 33 mmol) was dissolved in THF (30 mL) and was added dropwise to the above solution. The reaction mixture was stirred at r.t. for a further 3 h. The reaction was quenched with H2O, and THF was removed in vacuo. The residue was then extracted with CH2Cl2 and the combined organic layer was washed with 1N HCl and saturated NaHCO3, dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with Hexane/EtOAc (1:1) to provide Compound 3 (4.6 g, 20 mmol, 60percent) as a white solid. 1H NMR (CDCl3, 400 MHz) delta 7.91 (m, 2H), 7.79 (m, 2H), 6.81-6.74 (m, 1H), 6.16-6.11(dt, J=1.6, 16.0 Hz, 1H), 4.49 (dd, J=1.6, 4.8 Hz, 2H), 2.27 (s, 3H); 13C NMR (CDCl3, 100 MHz): delta 197.7, 167.7, 139.7, 134.4, 131.9, 131.8, 123.7, 123.6, 38.3, 27.2; MS (ESI, positive) m/z calcd. for C13H12NO3 [M+H]+: 230, found: 230.

The synthetic route of 2913-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF DELAWARE; Zhuang, Zhihao; Li, Guorui; (15 pag.)US9605297; (2017); B2;,
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Synthetic Route of 141452-01-9, A common heterocyclic compound, 141452-01-9, name is Methyl indoline-5-carboxylate, molecular formula is C10H11NO2, 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.

(R)-methyl l-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2- yl)indoline-5-carboxylate (i?)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one (44.2 mg, 0.150 mmol, 1 eq), methyl indoline-5-carboxylate (31.9 mg, 0.180 mmol, 1.2 eq), Pd2dba3 (6.9 mg, 0.0075 mmol, 5 mol%), XPhos (10.7 mg, 0.0225 mmol, 15 mol%) and K2C03 (82.9 mg, 0.60 mmol, 4 eq) were dissolved in tBuOH (1.5 mL, 0.1 M) and heated to 100 C for 21 hours. The mixture was filtered through celite, washed with DCM and condensed. Purification by column chromatography (ISCO, 4 g silica column, 0-100% EtOAc/hexanes, 18 minute gradient) gave the desired product as a yellow oil (43.4 mg, 0.0997 mmol, 66%). 1H NMR (400 MHz, Chloroform-;/) delta 8.30 (d, J= 8.6 Hz, 1H), 7.89 (dd, J= 8.6, 1.8 Hz, 1H), 7.82 (d, J= 1.3 Hz, 1H), 7.76 (s, 1H), 4.47 (p, J= 8.5 Hz, 1H), 4.32 – 4.19 (m, 3H), 3.88 (s, 3H), 3.33 (s, 3H), 3.18 (t, J= 8.8 Hz, 2H), 2.21 – 2.11 (m, 1H), 2.04 – 1.98 (m, 1H), 1.86 (ddt, J= 16.3, 8.7, 4.4 Hz, 4H), 1.76 – 1.62 (m, 4H), 0.87 (t, J= 7.5 Hz, 3H). 13C NMR (100 MHz, cdcl3) delta 167.22, 163.83, 154.78, 152.04, 148.37, 137.77, 132.00, 130.05, 125.80, 121.94, 115.94, 113.23, 60.15, 58.76, 51.72, 49.52, 29.62, 29.18, 28.13, 27.07, 26.65, 23.36, 23.02, 9.17. LCMS 436.49.

The synthetic route of 141452-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; BRADNER, James, E.; GRAY, Nathanael; QI, Jun; MCKEOWN, Michael, R.; BUCKLEY, Dennis; WO2015/117055; (2015); A1;,
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