Category: 200049-46-3

Related Products of 200049-46-3,Some common heterocyclic compound, 200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-one, molecular formula is C8H6BrNO, 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.

7-bromo-2,3-dihydro-lH-isoindol-l-one (5.7 g, 26.88 mmol) was added to sulfuric acid (60 ml) at 0C. The resulting mixture was stirred at 0C for 30 minutes. Then N-iodosuccinimide (9.07 g, 40.32 mmol) was added in one portion and the resulting suspension stirred at 0C for 2 hours. The reaction mixture was poured into ice water, causing a precipitate to form. The precipitate was extracted with ethyl acetate (3 x 200 ml). Both organic and aqueous phases contained precipitates. The organic phase was washed with 10% Na S C (200 ml) to remove excess iodine. The organic layer was dried with sodium sulphate, filtered and evaporated to afford 7-bromo-6-iodo-2,3-dihydro-lH-isoindol-l-one (7.2 g, 79%) as a white solid. 1H NMR (400 MHz, DMSO, 30C) 4.11 (2H, s), 7.43 (1H, d), 7.83 (1H, d), 8.90 (1H, s). m/z: ES+ [M+H]+ = 338.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Bromo-2,3-dihydro-isoindol-1-one, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; KETTLE, Jason, Grant; BAGAL, Sharanjeet, Kaur; EATHERTON, Andrew, John; FILLERY, Shaun, Michael; ROBB, Graeme, Richard; LAMONT, Scott, Gibson; KEMMITT, Paul, David; GOLDBERG, Frederick, Woolf; (158 pag.)WO2019/215203; (2019); A1;,
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200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-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. Recommanded Product: 7-Bromo-2,3-dihydro-isoindol-1-one

[00309] To a solution of 7-bromoisoindolin-l-one 1 (212 mg, 1.0 mmol) in MeCN (5.0 mL) was added CS2CO3 (652 mg, 2.0 mmol). The reaction mixture was stirred at rt for 15 min then cooled to 0-5 C. Benzyl bromide (274 mg, 1.6 mmol) was added dropwise. The reaction mixture was allowed to warm to rt and stirred for 16 h. The mixture was partitioned between EtOAc and water and the aqueous layer extracted with EtOAc. The combined organic layers were washed with water and brine, dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified (silica gel; eluting with 20% EtOAc in hexanes) to afford compound 2 (220 mg, 73%) as a yellow solid. 1H MR (400 MHz, CD3OD): delta 7.68 (m, 1H), 7.46 – 7.54 (m, 2H), 7.32 – 7.41 (m, 5H), 4.83 (s, 2H), 4.37 (s, 2H).

The synthetic route of 200049-46-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIDECAR THERAPEUTICS, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John. H.; (178 pag.)WO2019/70742; (2019); 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. 200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-one, A new synthetic method of this compound is introduced below., category: indolines-derivatives

A suspension of 2-borono-5-benzyloxy-indole-l-carboxylic acid tert-butyl ester Compound Id (31.2 g, 84.9 mmol), Compound Ic (12.0 g, 56.6 mmol), Pd(OAc)2 (254 mg, 1.13 mmol), DDBPP (464 mg, 1.13 mmol), K3PO4 (freshly powdered, 36.0 g, 170 mmol) and H2O (3.05 mL, 170 mmol) was stirred with an overhead mechanical stirrer for 24 hours at 25 C. The reaction mixture was diluted with H2O (1 L) and extracted with EtOAc/ THF (3/1, 3 X 300 mL). The organic extracts were dried with Na2SO4 and concentrated. The residue was purified by column chromatography (SiO2, 5-100% THF/Hex) to yield 5~benzyloxy-2-(3-oxo-2,3-dihydro-lH-isoindol-4-yl)-indole-l- carboxylic acid tert-butyl ester Compound 32 (23.2 g, 90%) as an off white solid. 1H NMR (300 MHz, CDCl3) delta 8.17 (d, J= 9 Hz, IH), 7.62-7.03 (m, HH), 6.51 (s, IH), 5.15 (s, 2 H), 4.44 (s, 2H), 1.29 (s, 9H); MS (ESI) m/z: 477 (MNa+).

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; JANSSEN PHARMACEUTICA, N.V.; WO2007/47646; (2007); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 200049-46-3, 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. 200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Using the procedure of Example 1 and Compound 19a in place of Compound Id, Compound Ic was converted to 7-(l-benzenesulfonyl-lH-indol-3-yl)-2,3-dihydro- isoindol-1-one Compound 19b, which was isolate as a white solid. 1H NMR (300 MHz, MeOD) 4.48 (s, 2H), 7.22 (dt, J = 1, 8 Hz, IH), 7.31 (dt, J = 1, 8 Hz, IH), 7.45- 7.75 (complex, 7H), 7.45-8.1 (complex, 4H); MS (ESI) m/z: 389 (MH+).

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, 7-Bromo-2,3-dihydro-isoindol-1-one, other downstream synthetic routes, hurry up and to see.

Synthetic Route of 200049-46-3, The chemical industry reduces the impact on the environment during synthesis 200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-one, I believe this compound will play a more active role in future production and life.

Similar to the procedure used to prepare Compound 32, Compound Ic was reacted with Compound 12a and Pd(OAc)2, P(?-tolyl)3, and 2N aqueous Na2CO3 in DMF to give Compound 23 as a clear, colorless oil. 1H NMR (400 MHz, CDCl3) 1.30 and 1.65 (rotamer A and B, two singlets, 9H), 4.42 (s, 2H), 6.25 (m, IH), 7.35-7.65 (complex, 5H); MS (ESI) m/z: 299 (MH+).

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, 7-Bromo-2,3-dihydro-isoindol-1-one, other downstream synthetic routes, hurry up and to see.

Electric Literature of 200049-46-3,Some common heterocyclic compound, 200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-one, molecular formula is C8H6BrNO, 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 1 -(3 -bromo- 1 -(tetrahydro-2H-pyran-4-yl)-6, 7-dihydro- 1H-pyrazolo[4, 3-c]pyridin-5(4H)-yl)ethanone (Intermediate H, 350 mg, 1.07 mmol) and bis(pinacolato)diboron(542 mg, 2.13 mmol) in dioxane (5.3 mL) was added KOAc (314 mg, 3.20 mmol), (2- dicyclohexylphosphino-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl)[2-(2?-amino- 1,1?- biphenyl)]palladium(II) methanesulfonate (26 mg, 0.032 mmol) and 2-(dicyclohexylphosphino)- 2?,4?,6?-triisopropylbiphenyl (31 mg, 0.064 mmol). The mixture was stirred at 80C for 16 hunder a nitrogen atmosphere. The reaction mixture was cooled to room temperature and 7- bromoisoindolin-1-one (113 mg, 0.533 mmol), K3P04.H20 (313 mg, 1.33 mmol), water (1.3 mL) and (2-dicyclohexylphosphino-2?,4?,6?-triisopropyl- 1,1 ?-biphenyl)[2-(2?-amino- 1,1?- biphenyl)]palladium(II) methanesulfonate (26 mg, 0.032 mmol) were added. The reaction mixture was stirred at 90 C for 4 h under a nitrogen atmosphere. The reaction mixture was thencooled to room temperature and concentrated in vacuo. The crude residue was dissolved indichloromethane (20 mL), dried over anhydrous MgSO4, filtered through celite and concentrated in vacuo. The mixture obtained was purified by silica gel chromatography (MeOH / iPrOAc = 1 10 to 1: 3) to give the title compound (144 mg, 36%) as a white solid. ?H NMR (400 IVIFIz, DMSO-d6, 23 / 24 H) 7.66 – 7.40 (m, 3H), 6.06 – 5.94 (m, 1H), 4.48 (d, J = 9.5 Hz, 2H), 4.62-4.41 (m, 1H),4.18(dd,J36.7, 11.6Hz,2H),3.99-3.77(m,2H),3.59-3.47(m,3H),2.82 (dt, J = 24.3, 5.9 Hz, 2H), 2.43 -2.30 (m, 2H), 2.17-2.06 (m, 3H), 1.93 (d, J = 13.2 Hz, 2H). LCMS M/Z (M+H) 381.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Bromo-2,3-dihydro-isoindol-1-one, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); 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. 200049-46-3, name is 7-Bromo-2,3-dihydro-isoindol-1-one belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Formula: C8H6BrNO

7-Bromo-2,3-dihydro-1H-isoindol-1-one (10 g, 47.16 mmol) was added to concentrated H2SO4 (80 mL) at 0 C. and the resulting solution stirred at 0 C. for 0.5 h. N-Iodosuccinimide (15.92 g, 70.74 mmol) was then added and the reaction mixture stirred at 0 C. for 2 h. The reaction mixture was poured on to ice and a precipitate collected by filtration. The solid collected was washed with sat. aq. sodium sulfite (200 ml), water (200 ml) and dried under vacuum to afford crude product as a brown solid. The crude product was triturated with MeOH and the solid obtained dried under vacuum to afford 7-bromo-6-iodo-2,3-dihydro-1H-isoindol-1-one (4.3 g, 27%) as white solid; 1H NMR (400 MHz, DMSO, 30 C.) 4.27 (2H, s), 7.37 (1H, d), 8.11 (1H, d), 8.74 (1H, s); m/z: ES+ [M+H]+=340.

The synthetic route of 200049-46-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; Kettle, Jason Grant; Bagal, Sharanjeet; Robb, Graeme Richard; Smith, James Michael; Goldberg, Frederick Woolf; Cassar, Doyle Joseph; Feron, James Lyman; US2019/177338; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 200049-46-3, 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 200049-46-3 as follows.

[00259] A stirred mixture of Int-A (200 mg, 0.984 mmol), 7-bromoisoindolin-l-one 1 (240 mg, 1.13 mmol), XPhos (47 mg, 0.098 mmol), Cs2C03 (800 mg, 2.46 mmol), and fert-butanol (7.8 mL) at rt, was purged with a stream of argon for 5 min. Pd2(dba)3 (90 mg, 0.098 mmol) was added and the vial was sealed and heated at 100 C for 16 h. The mixture was cooled to rt and concentrated under reduced pressure. The residue was partitioned between DCM and water. The organic layer was separated and the aq layer re-extracted with additional DCM. The combined organic layers were dried (Na2S04), filtered, and concentrated under reduced pressure. The residue was purified via reverse-phase preparative HPLC (X-Select CSH C18 250 chi 19 mm, 5mupiiota column; eluting with 10-90% MeCN/H20 containing 0.05% TFA, over 30 min) to afford compound 2 (52 mg, 12%) as a yellow solid. LCMS Mass: 335.0 (M++l).

According to the analysis of related databases, 200049-46-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIDECAR THERAPEUTICS, INC.; ROWBOTTOM, Martin W.; HUTCHINSON, John. H.; (178 pag.)WO2019/70742; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem