346-34-9 Archives - Indolines-derivatives

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Reference of 346-34-9, 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. 346-34-9, name is 4-Fluoroindoline-2,3-dione belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 1 A6-bromo-2-(trifluoromethyl)quinoline-4-carboxylic acid 300 mg (1.33 mmol) of 5-bromo-1 H-indole-2,3-dione was suspended in 3 mL water in a microwave vial. 82 mg ( 1.46 mmol) potassium hydroxide, 152 muL (2.65 mmol) acetic acid and 152 mg (1.86 mmol) sodium acetate were added so that the pH was around 5. The solution was cooled to 10 C and 238 muL (2.65 mmol) 1 ,1,1 -trifluoroacetone was added rapidly, the microwave vial was sealed and heated in the microwave for 2 h at 120 C. The reaction was stopped by the addition of 10% aqueous hydrochloric acid solution and the resulting precipitate was isolated by filtration, washed with water and dried in a vacuum drying cabinet at 50 C overnight to obtain 409 mg (1.28 mmol, 96%) of the desired title compound .In analogy to intermediate 1 A, 300 mg (1.82 mmol) 4-fluoro-1 H-indole-2,3-dione was heated with 900 muL (9.08 mmol) 1 -cyclopropylethanone, 112 mg (2.00 mmol) potassium hydroxide, 208 muL (3.63 mmol) acetic acid and 209 mg (2.54 mmol) sodium acetate in 3 mL water for 6 h at 150 C in the microwave. The reaction mixture was quenched with 10% hydrochloric acid solution and filtered. The filtrate was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over sodium sulfate, filtered and evaporated to obtain 120 mg (0.52 mmol, 29%) of the desired title compound after drying.1 H NMR (400 MHz, DMSO d6): delta (ppm) = 1.10 – 1.17 (m, 4 H), 2.40 – 2.47 (m, 1 H), 7.52 – 7.60 (m, 2 H), 7.93 (s, 1 H), 8.35 – 8.41 (m, 1 H,) 13.98 (br. s, 1 H).

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-Fluoroindoline-2,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; HEISLER, Iring; MUeLLER, Thomas; SIEBENEICHER, Holger; BUCHMANN, Bernd; CLEVE, Arwed; GUeNTHER, Judith; KOPPITZ, Marcus; HEROULT, Melanie; NEUHAUS, Roland; PETRUL, Heike; QUANZ-SCHOeFFEL, Maria; WO2015/91428; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Extended knowledge of C8H4FNO2

These common heterocyclic compound, 346-34-9, name is 4-Fluoroindoline-2,3-dione, 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. Recommanded Product: 4-Fluoroindoline-2,3-dione

General procedure: Compound 2e was prepared from 4-fluoro-1H-indole-2,3-dione 1c and dl-leucine in a similar manner to that described for the synthesis of compound 2a and obtained in 70% yield as a yellow solid. 1H NMR (400 MHz, DMSO-d6) delta 0.85-0.90 (m, 6H), 1.28-1.39 (m, 2H), 1.58-1.67 (m, 1H), 1.92-2.03 (m, 1H), 2.11-2.22 (m, 1H), 2.91-3.04 (m, 1H), 3.15 (s, 3H), 3.38-3.42 (m, 1H), 3.44-3.49 (m, 1H), 6.60-6.69 (m, 2H), 7.15-7.23 (m, 1H), 10.51 (s, 1H). MS m/z 321 (M+H)+.

The synthetic route of 4-Fluoroindoline-2,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article in Press; Ito, Masahiro; Iwatani, Misa; Yamamoto, Takeshi; Tanaka, Toshio; Kawamoto, Tomohiro; Morishita, Daisuke; Nakanishi, Atsushi; Maezaki, Hironobu; Bioorganic and Medicinal Chemistry; (2017);,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Research on new synthetic routes about 4-Fluoroindoline-2,3-dione

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.

Electric Literature of 346-34-9, A common heterocyclic compound, 346-34-9, name is 4-Fluoroindoline-2,3-dione, molecular formula is C8H4FNO2, 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.

Intermediate 1 A6-bromo-2-(trifluoromethyl)quinoline-4-carboxylic acid 300 mg (1.33 mmol) of 5-bromo-1 H-indole-2,3-dione was suspended in 3 mL water in a microwave vial. 82 mg ( 1.46 mmol) potassium hydroxide, 152 muL (2.65 mmol) acetic acid and 152 mg (1.86 mmol) sodium acetate were added so that the pH was around 5. The solution was cooled to 10 C and 238 muL (2.65 mmol) 1 ,1,1 -trifluoroacetone was added rapidly, the microwave vial was sealed and heated in the microwave for 2 h at 120 C. The reaction was stopped by the addition of 10% aqueous hydrochloric acid solution and the resulting precipitate was isolated by filtration, washed with water and dried in a vacuum drying cabinet at 50 C overnight to obtain 409 mg (1.28 mmol, 96%) of the desired title compound .1 H NMR (300 MHz, DMSO d6): delta (ppm) = 8.14 (dd, 1 H), 8.21 (d, 1 H), 8.32 (s, 1 H), 9.09 (d, 1 H), 14.50 (br. s. , 1 H)._In analogy to intermediate l, 300 mg (1.81 mmol) 4-fluoro-1H-indole-2,3-dione washeated with 326 pL (3.63 mmoL) 1,1,1-trifluoroacetone, 112 mg (1.99 mmoL)potassium hydroxide, 208 pL (3.63 mmo[) acetic acid and 209 mg (2.54 mmoL) sodium acetate in 3 mL water for 2 h at 100CC in the microwave to obtain 315 mg (1.22 mmol, 67%) of the desired title compound after aqueous work-up.1H NMR (400MHz, DMSO d6): 6 (ppm) = 783 -7.92 (m, 1 H), 8.09 (dd, 1 H), 8.25 (s, 1 H), 8.90 (dd, 1 H), 14.50 (br. 5., 1 H).