Category: 337536-15-9

337536-15-9, name is 4-Bromoisoindolin-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. Computed Properties of C8H6BrNO

Step 4: Preparation of 4-bromo-7-nitroisoindolin-1-one (5) To a solution of 4-bromoisoindolin-1-one 4 (3.0 g, 14.1 mmol) in conc. H2SO4 (6 mL) at 0 C. was added dropwise a solution of conc. HNO3 (1 mL) in conc. H2SO4 (6 mL) The resulting mixture was then stirred at room temperature overnight, then poured over ice, and filtered. The filter cake was washed with water, MTBE, dried in vacuo to give the title product 5 (3.0 g). 1H NMR (400 MHz, DMSO-d6) delta 9.17 (s, 1H), 8.06-8.04 (d, J=8.4 Hz, 1H), 7.89-7.87 (d, J=8.4 Hz, 1H), 4.39 (s, 2H).

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GREEN CROSS CORPORATION; CHOI, Soongyu; PARK, Eun-Jung; SEO, Hee Jeong; KONG, Younggyu; SON, Ickhwan; MA, Sang-ho; CHA, Man-Young; KIM, Mi-Soon; PARK, Kisoo; (143 pag.)US2016/311772; (2016); 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. 337536-15-9, name is 4-Bromoisoindolin-1-one, A new synthetic method of this compound is introduced below., Product Details of 337536-15-9

EXAMPLE 54A 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-isoindolinone A suspension of Example 1C (10.6 g, 50 mmol) and 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (15.23 g, 60 mmol) in DMF (390 mL) was stirred until a clear yellow solution was obtained. The solution was then treated with potassium acetate (14.72 g, 150 mmol), degassed with nitrogen, treated with [1.1′-bis(diphenylphosphino)-ferrocene]dichloropalladium [II].CH2Cl2 (7 g, 8.5 mmol) and heated to 90 C. overnight. The reaction was cooled to room temperature and filtered through diatomaceous earth (Celite), and concentrated. The concentrate was partitioned between water and ethyl acetate and filtered through diatomaceous earth (Celite). The organic phase was dried (Na2SO4), filtered, and concentrated. The crude product was purified by silica gel chromatography eluding with 100% ethyl acetate and triturated from hexanes to give 4.56 g (35% yield) of the desired product. m.p.: 189-191 C.

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; Curtin, Michael L.; Davidsen, Steven K.; Frey, Robin R.; Heyman, Howard R.; Holms, James H.; Michaelides, Michael; Steinman, Douglas H.; US2005/26976; (2005); 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 337536-15-9 as follows. SDS of cas: 337536-15-9

EXAMPLE 854-(6-Amino-5-((R)-1-(5-fluoro-2-(2H-1 ,2,3-triazol-2-yl)phenyl)ethoxy)pyridin-3- yl)isoindolin-1-oneA mixture of preparation 45 (100 mg, 0.264 mmol), 4,4,5,5,4′,4,,5′,5,-Octamethyl- [2,2′]bi[[1 ,3,2]dioxaborolanyl] (1 14 mg, 1.7 eq), and potassium acetate (90.7 mg, 3.5 eq) in DMSO (1.0 mL) was deoxygenated with N2 bubbler for 30 minutes before addition of the Pd(dppf)CI2 (9.5 mg, 0.05 eq). The mixture was then heated in 80C oil bath for 3 hr. LCMS indicated disappearance of starting bromide. To the crude boronate mixture was added 4-bromoisoindolin-1-one (84 mg, 1.5 eq), CsF (120 mg, 3.5 eq) and MeOH (2 ml_). The mixture was thoroughly degassed and Pd(dppf)Cl2 (9.5 mg, 0.05 eq) was added. The mixture was heated in the microwave at 120 C for 1 hr. LCMS showed the desired product mass. Mixture was filtered and purified with a reverse phasepreparative HPLC under acidic condition to give the title compound as an amorphous white solid (57.8 mg, 50.9%).1H NMR (600 MHz, DMSO-d6) delta ppm 1.59 (d, J=6.14 Hz, 3 H), 4.07 – 4.21 (m, 1 H), 4.23 – 4.34 (m, 1 H), 5.56 (q, J=6.06 Hz, 1 H), 6.19 (s, 2 H), 6.77 (s, 1 H), 7.34 (td, J=8.26, 2.94 Hz, 1 H), 7.41 (d, J=7.42 Hz, 1 H), 7.51 (t, J=7.55 Hz, 1 H), 7.57 (s, 1 H), 7.63 – 7.67 (m, 1 H), 7.70 – 7.72 (m, 1 H), 7.72 (d, J=1.28 Hz, 2 H), 8.20 (s, 1 H), 8.64 (s, 1 H).

According to the analysis of related databases, 337536-15-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Related Products of 337536-15-9, A common heterocyclic compound, 337536-15-9, name is 4-Bromoisoindolin-1-one, molecular formula is C8H6BrNO, 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 4-bromoisoindolin-1-one (1.0 g, 4.72 mmol) and benzophenone hydrazone (2.78 g, 14.15 mmol) in 1,4-dioxane (25 mL) at room temperature under nitrogen, BINAP (587 mg, 0.94 mmol), palladium (II) acetate (212 mg, 0.94 mmol) and sodium t-butoxide (1.36 g, 11.15 mmol) were added and the mixture was heated at 100 C. for 16 h. The resultant mixture was cooled to room temperature, filtered, and the filtrate concentrated under reduced pressure to give the crude product, which was purified by flash chromatography (SiO2, heptane-ethyl acetate gradient). Pure fractions were combined and concentrated. The product was dried under reduced pressure to afford 4-(2-(diphenylmethylene)hydrazinyl)isoindolin-1-one, cpd 133a (1.544 g, 90.7% yield). MS m/z 328.0 (M+H)+

The synthetic route of 337536-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Lu, Tianbao; Connolly, Peter J.; Cummings, Maxwell David; Barbay, Joseph Kent; Kreutter, Kevin D.; Wu, Tongfei; Diels, Gaston Stanislas Marcella; Thuring, Jan Willem; Philippar, Ulrike; Edwards, James Patrick; Shen, Fang; (202 pag.)US2019/381019; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem