Category: 74572-29-5

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. 74572-29-5, name is 5-Chloroisoindolin-1-one, A new synthetic method of this compound is introduced below., Computed Properties of C8H6ClNO

[A] 2-(8-Amino-5,6,7,8-tetrahydro-isoquinolin-4-yl)-5-chloro-2,3-dihydro-isoindol-1-one In a 25 mL sealed tube, 5-chloro-2,3-dihydro-isoindol-1-one (80.1 mg, 4.8 mmol), 4-bromo-5,6,7,8-tetrahydroisoquinolin-8-ylamine (intermediate B-12 [A], 999 mg, 4.4 mmol), CuI (200 mg, 1.1 mmol), Cs2CO3 (3.0 g, 9.2 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.4 mL, 3.2 mmol) were dissolved in dioxane (16 mL). The resulting reaction mixture was heated at 150 C. for 3 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2*125 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by silica gel flash chromatography (30-100% EtOAc-hexane gradient) to yield the title compound (1.2 g, 80%) as a light yellow solid. MS: 314.2 (M+H+).

The synthetic route of 74572-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Aebi, Johannes; Amrein, Kurt; Chen, Wenming; Hornsperger, Benoit; Kuhn, Bernd; Liu, Yongfu; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; Wang, Zhanguo; Zhou, Mingwei; US2013/143863; (2013); 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. 74572-29-5, name is 5-Chloroisoindolin-1-one, A new synthetic method of this compound is introduced below., Product Details of 74572-29-5

In a 25 mL sealed tube, 5-chloro-2,3-dihydro-isoindol-1-one (80.1 mg, 4.8 mmol), 4-bromo-6,7-dihydro-5H-[2]pyrindin-7-ylamine (intermediate B-18 [C], 937 mg, 4.4 mmol), CuI (200 mg, 1.1 mmol), Cs2CO3 (3.0 g, 9.2 mmol) and (+)-(S,S)-1,2-diaminocyclohexane (0.4 mL, 3.2 mmol) were dissolved in dioxane (16 mL). The resulting reaction mixture was heated at 150 C. for 3 hours before it was poured into H2O (50 mL) and extracted with EtOAc (2×125 mL). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a crude product which was purified by silica gel flash chromatography (30-100% EtOAc-hexane gradient) to yield the title compound (1.02 g, 80%) as a light yellow solid. MS: 300.2 (M+H+).

The synthetic route of 74572-29-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoffmann-La Roche Inc.; Aebi, Johannes; Amrein, Kurt; Chen, Wenming; Hornsperger, Benoit; Kuhn, Bernd; Liu, Yongfu; Maerki, Hans P.; Mayweg, Alexander V.; Mohr, Peter; Tan, Xuefei; Wang, Zhanguo; Zhou, Mingwei; US2013/143863; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 74572-29-5, name is 5-Chloroisoindolin-1-one, molecular formula is C8H6ClNO, 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. name: 5-Chloroisoindolin-1-one

A mixture of 5-chloro-2,3-dihydro-isoindol-1-one (71 mg, 0.43 mmol), 5-iodo-3?,4?,5?,6?- tetrahydro-2?H- [3 ,4?]bipyridinyl- 1 ?-carboxylic acid tert-butyl ester (150 mg, 0.38 mmol) (example 15 [C]), CuT (22 mg, 0.11 mmol), (iS, 2S)-cyclohexane- 1 ,2-diamine (0.03 mL,0.22 mmol) and K3P04 (165 mg, 0.77 mmol) in dioxane (10 mL) was stuffed at 120C for2 hours. The resulting mixture was poured into water (50 mL) and the aqueous was exacted with EtOAc (30 mL, 3x). The combined organic layers were washed with brine, dried over anhy. Na2SO4 and concentrated in vacuo to get a crude product which was purified by column chromatography (EtOAc: PE = 1:1) to afford title compound (100 mg,61%) as a yellow foam. MS: 428.1 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 74572-29-5, its application will become more common.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LI, Dongbo; LIU, Yongfu; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; WANG, Lisha; WU, Jun; ZHOU, Mingwei; WO2014/191336; (2014); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 74572-29-5, 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 74572-29-5 as follows.

A suspension of copper (I) iodide (88 mg, 0.46 mmol), l-(3-bromophenyl)ethan-l-ol (1.85 g, 9.19 mmol) potassium carbonate (0.65 g, 4.59 mmol) and 5-chloroisoindolin-l-one (0.77 g, 4.59 mmol) in anhydrous A’ A’-d i m e th y 1 fo rm am i dc (3.8 mL) was purged with nitrogen and heated at 150 C for 16 h. The mixture was diluted with 10% ammonium hydroxide solution. General Work-up Procedure 1 was followed. The residue was purified on silica gel (ethyl acetate in hexanes 40% isocratic) to give the title compound as an off-white solid. Yield: 0.42 g (32%).

According to the analysis of related databases, 74572-29-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NURIX THERAPEUTICS, INC.; BARSANTI, Paul A.; BENCE, Neil F.; GOSLING, Jennifa; SAHA, Anjanabha; TAHERBHOY, Asad M.; ZAPF, Christoph W.; BOYLE, Kathleen; CARDOZO, Mario; MIHALIC, Jeffrey; LAWRENZ, Morgan; GALLOP, Mark; BRUFFEY, Jilliane; CUMMINS, Thomas; ROBBINS, Daniel; TANAKA, Hiroko; WANG, Chenbo; COHEN, Frederick; PALMER, Wylie; SANDS, Arthur T.; SHUNATONA, Hunter; (968 pag.)WO2019/148005; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem