Category: 70478-63-6

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. 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, A new synthetic method of this compound is introduced below., name: 4-Bromoisoindoline-1,3-dione

[00287] To a solution of 4-bromoisoindole-l,3-dione 1 (226 mg, 1.0 mmol) in DMF (8 mL) was added Cs2C03 (652 mg, 2.0 mmol). The mixture was cooled to 0-5 °C and PMB-Br (302 mg, 1.5 mmol) was added dropwise. The reaction was allowed to warm to rt and stirred for 16 h. The mixture was partitioned between water and EtOAc, and the aqueous layer was 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 20percent EtOAc in hexanes) to afford compound 2 (208 mg, 74percent) as a yellow solid. 1H NMR (400 MHz, CDC13): delta 7.80 – 7.83 (m, 2H), 7.60 (m, 1H), 7.53 – 7.57 (m, 2H), 6.85 – 6.90 (m, 2H), 4.80 (s, 2H), 3.79 (s, 3H).

The synthetic route of 70478-63-6 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

Related Products of 70478-63-6, A common heterocyclic compound, 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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.

[00290] To a solution of 4-bromoisoindole-l,3-dione 1 (226 mg, 1.0 mmol) in MeCN (5 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. lodomethane (0.2 mL, 3.0 mmol) added dropwise and the reaction mixture was allowed to warm to rt and stirred for a further 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, brine, then dried (Na2S04), filtered and concentrated under reduced pressure. The residue was purified (silica gel; eluting with 20percent EtOAc in hexanes) to afford the compound 2 (220 mg, 92percent) as a yellow solid. 1H MR (400 MHz, DMSO-i): delta 7.97 (m, 1H), 7.86 (m, 1H), 7.70 (m, 1H), 3.03 (s, 3H).

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

These common heterocyclic compound, 70478-63-6, name is 4-Bromoisoindoline-1,3-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. Quality Control of 4-Bromoisoindoline-1,3-dione

Step b. A mixture of 7-bromo-3-hydroxy-3-methylisoindolin-l-one and 4-bromo-3-hydroxy-3 -methyl isoindolin-l-one (12.00 g, 49.8 mmol) in DCM (100 ml) was cooled to -40¡ãC. Triethylsilane (80.4 ml, 498 mmol) was added to the reaction mixture at -40¡ãC under N2 atmosphere. Boron trifluoride diethyletherate (18.7 ml, 149.4 mmol) was added to the reaction mixture at -40¡ãC under N2 atmosphere. The reaction mixture was stirred at 0¡ãC for 1 h. The resulting reaction mixture was combined with two other batches prepared on the same scale by an identical method. The resulting reaction mixture was poured into NaHC03 solution (500 ml) and extracted with the DCM (3 x 1000 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The crude material obtained was purified by column chromatography (3percent EtOAc in DCM) yielding 7-bromo-3-methylisoindolin-l-one (9.200 g, 40.9 mmol). LCMS: Method A, 1.521 min, MS: ES+ 226.11, 228.11; NMR (400 MHz, CDC13) delta ppm 7.61 (dd, J=7.2, 1.2 Hz, 1 H), 7.43 – 7.38 (m, 3 H), 7.68 – 7.63 (m, 1 H), 1.52 (d, J=6.8 Hz, 3 H).

The synthetic route of 4-Bromoisoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Some common heterocyclic compound, 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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. Product Details of 70478-63-6

Step a. To a solution of 4-bromoisoindoline-l,3-dione (CAS Number 70478-63-6, 15.00 g, 66.4 mmol) in DCM (150 ml) was dropwise added methyl magnesium bromide (1 M in THF) (199 ml, 199 mmol) at 0¡ãC under N2 atmosphere. The reaction mixture was stirred at rt for 2 h. The reaction mixture was combined with three other batches prepared on the same scale by an identical method. The resulting reaction mixture was poured in to NH4C1 solution (500 ml) and extracted with the DCM (3 x 1 L). The combined organic phases was dried over Na2S04, filtered and concentrated under reduced pressure. The crude material was purified by column chromatography (30-32 percent EtOAc in hexane) yielding a mixture of 7-bromo-3-hydroxy-3-methylisoindolin-1-one and 4-bromo-3-hydroxy- 3-methylisoindolin-1-one (37.00 g, 153.6 mmol). LCMS: Method A, 1.435 min, MS: ES+ 242.33, 244.33.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 70478-63-6, its application will become more common.

Reference:
Patent; MISSION THERAPEUTICS LIMITED; GIBSON, Karl Richard; JONES, Alison; KEMP, Mark Ian; MADIN, Andrew; STOCKLEY, Martin Lee; WHITLOCK, Gavin Alistair; WOODROW, Michael D; (241 pag.)WO2017/158388; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Electric Literature of 70478-63-6,Some common heterocyclic compound, 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, molecular formula is C8H4BrNO2, 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.

Example 32B tert-butyl (1S)-2-{[5-(1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl)pyridin-3-yl]oxy}-1-(1H-indol-3-ylmethyl)ethylcarbamate A solution of Example 32A (0.2 g, 0.31 mmol) and 6-bromophthalimide (0.084 g, 0.4 mmol) in DMF (2 mL) was treated with Pd2 dba3 (0.04 g, 0.02 mmol), tri-o-tolylphosphine (0.02 g, 0.01 mmol), and triethylamine (0.06 mL, 0.4 mmol). The reaction was heated to 75¡ã C. for 6 hours in a sealed tube and concentrated. The residue was purified by flash column chromatography on silica gel with 1:1 hexanes/ethyl acetate to provide the desired product (0.116 g, 55percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromoisoindoline-1,3-dione, its application will become more common.

Reference:
Patent; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

70478-63-6, The chemical industry reduces the impact on the environment during synthesis 70478-63-6, name is 4-Bromoisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

A mixture of 3-bromophthalimide (10.0 g, 44.2 mmol), potassium carbonate (12.2 g, 88.5 mmol) and potassium iodide (50 mg, 0.30 mmol) are stirred in 80 mL DMF for 15 min. The reaction mixture is cooled to 0 0C, methyl iodide (3.04 mL, 48.7 mmol) is added and the reaction mixture is stirred overnight at RT. The reaction mixture is filtered, the solids are washed with DMF and the filtrate is poured in water. The mixture is extracted with ethyl acetate and the combined organic phases are washed several times with water, dried over MgSO4 and concentrated in vacuo. Yield: 7.10 g.

The chemical industry reduces the impact on the environment during synthesis 4-Bromoisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/112565; (2009); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem