Category: 1035235-27-8

Recommanded Product: tert-Butyl 4-bromoisoindoline-2-carboxylate, Chemistry built the modern world, from the materials that make up the everyday objects around us, the batteries in our devices and cleaning products that help to maintain sanitation.

A mixture of tert-butyl 4-bromoisoindoline-2-carboxylate (1.70 g, 5.70 mmol),4,4,4?,4?,5 ,5 ,5 ?,S ?-octamethyl-2,2?-bi(1 ,3 ,2-dioxaborolane) (1.74 g, 6.84 mmol), potassiumacetate (1.68 g, 17.1 mmol), and PdC12(dppf) DCM adduct (0.466 g, 0.570 mmol) in 1,4-dioxane (25 mL) was bubbled with nitrogen and stirred at 80 C overnight. The mixture was cooled to room temperature, diluted with EtOAc, washed with water, dried and concentrated. The residue was subjected to colunm chromatography on silica gel, eluting with EtOAc-hexanes (gradient from 0-30%), to provide tert-butyl 4-(4,4,5 ,5 -tetramethyl5 1 ,3,2-dioxaborolan-2-yl)isoindoline-2-carboxylate as a white solid (1.50 g, 76% yield).

As always, wish you can browse a selection of our May HOT articles below about tert-Butyl 4-bromoisoindoline-2-carboxylate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; AHMAD, Saleem; BATT, Douglas G.; LIU, Qingjie; MACOR, John E.; TINO, Joseph A.; WATTERSON, Scott Hunter; NAIR, Satheesh Kesavan; MAISHAL, Tarun Kumar; (247 pag.)WO2016/65236; (2016); A1;,
Indoline – Wikipedia,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1035235-27-8

Step 5: tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate A solution of tert-butyl 4-bromo-1,3-dihydro-2H-isoindole-2-carboxylate (0.80 mmol), bis(pinacolato)diboron (0.96 mmol) and potassium acetate (2.5 mmol) in DMF (4 mL) was degassed. To this solution was added PdCl2dppf (1:1 complex with DCM, 0.04 mmol). The reaction mixture was heated at 85 C. for 4 hr and then allowed to cool to rt and diluted with EtOAc. The solution was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate (0.64 mmol, 80%) as a white solid. LCMS: (FA) ES+346.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1035235-27-8.

Reference:
Patent; Millennium Pharmaceuticals, Inc.; US2008/171754; (2008); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1035235-27-8, SDS of cas: 1035235-27-8

Carbon dioxide (g, 60 atm) was introduced into a lOO-mL pressure tank reactor containing a solution of tert-butyl 4-bromo-2,3-dihydro-lH-isoindole-2-carboxylate (2.00 g, 6.71 mmol), triethylamine (2.80 mL, 20.1 mmol), and [l,l?-bis(diphenylphosphino)ferrocene]- dichloropalladium (II), complex with dichloromethane (820 mg, 1.12 mmol) in ethanol (50 mL). The resulting mixture stirred overnight at 120 C. The reaction was concentrated under vacuum and then quenched by the addition of 50 mL of water. The resulting solution was extracted with 3×50 mL of ethyl acetate, washed with 100 mL of brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with ethyl acetate/petroleum ether (1 : 10)) to afford 2-(tert-butyl) 4-ethyl isoindoline-2,4-dicarboxylate (1.67 g, 85%) as an off-white solid. MS: (ESI, m/z): 292[M+H]+

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Synthetic Route of 1035235-27-8, A common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, molecular formula is C13H16BrNO2, 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.

Step a. To a stirred solution of tert-butyl 4-bromoisoindoline-2-carboxylate (Intermediate 1, 0.35 g, 1.185 mmol) in 1,4-dioxane: water (4: 1; 20 ml) was added Cs2C03 (0.77 g, 2.371 mmol) at rt under nitrogen. The reaction was purged with nitrogen for 15 min. Pd(PPh3)4 (0.14 g, 0.118 mmol) was added to the reaction mixture and purged with nitrogen for 10 min. 3- (Methoxycarbonyl)phenylboronic acid (CAS Number 99769-19-4; available from Combi Blocks) (0.26 g, 1.422 mmol) was added to the reaction mixture. The reaction mixture was heated at 80C for 24 h. The resulting reaction mixture was cooled to rt, poured into water (20 ml) and extracted with EtOAc (3 x 50). The combined organic phase was washed with brine (80 ml). The organic phase was separated, dried over Na2S04, filtered and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography (5% EtOAc in hexane) yielding tert-butyl 4-(3- (methoxycarbonyl)phenyl)isoindoline-2-carboxylate (0.33 g, 0.932 mmol). LCMS: Method A, 2.782 min, MS: ES+ 298.4 (M-56); 1H NMR (400 MHz, CDC13) delta ppm 8.04 – 8.11 (m, 2 H), 7.62 (d, J=7.2 Hz, 1H), 7.49 – 7.58 (m, 2 H), 7.40 (t, J=7.2 Hz, 1H), 7.31 – 7.33 (m, 1H), 4.69 – 4.79 (m, 4 H), 3.95 (s, 3 H), 1.53 (s, 9 H).

The synthetic route of 1035235-27-8 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

Reference of 1035235-27-8, These common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, 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.

Step f. Bis(pinacolato)diboron (87.5 g, 344 mmol) was added to a solution of tert-butyl 4- bromoisoindoline-2-carboxylate (85.6 g, 287 mmol) in 1,4-dioxane (850 ml), followed by potassium acetate (56.2 g, 574 mmol), and the resulting mixture was degassed with nitrogen for 15 min. Pd(dppf)Cl2 (21 g, 28.7 mmol) was added to the reaction flask and the resulting mixture was heated at 100C for 6 h. Upon completion of the reaction, as determined by LCMS, the mixture was cooled to rt and filtered through a pad of Celite, washing with EtOAc (2 chi 50 ml). The filtrate was evaporated to dryness under vacuum to give a black oily residue, which was dissolved in DCM and passed through a silica pad, eluting with DCM. The solvent was subsequently removed under vacuum to give a solid, which was triturated with hexane (200 ml) and dried under vacuum at rt to give the desired product as a white solid (88 g, 89%). LCMS (Method R): rt 3.36 min, m/z 346, 290 (-iBu), 246 (-Boc) [M+H]+; NMR (400 MHz, DMSO-d6) delta ppm 7.62-7.54 (m, 1H), 7.48-7.41 (m, 1H), 7.33-7.25 (m, 1H), 4.70-4.62 (m, 2H), 4.60-4.53 (m, 2H), 1.49-1.43 (m, 9 H), 1.33-1.27 (m, 12 H).

The synthetic route of 1035235-27-8 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

Application of 1035235-27-8, These common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, 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.

Step a. To a stirred solution of tert-butyl 4-bromoisoindoline-2-carboxylate (Intermediate 1, 0.2 g, 0.671 mmol) in l,4-dioxane:water (4.1; 5 ml) were added Cs2C03 (0.44 g, 1.342 mmol) and 1-methyl- lH-pyrazole-4-boronic acid pinacol ester (CAS Number 761446-44-0; available from Combi Blocks) (0.17 g, 0.805 mmol) at rt. The reaction mixture was degassed for 20 min. Pd(PPh3)4 (0.077 g, 0.067 mmol) was added to the reaction mixture at rt. The reaction mixture was heated at 85C for 30 min. The resulting reaction mixture was cooled to rt, diluted with water (100 ml) and extracted with EtOAc (3 x 80 ml). The combined organic phase was separated, dried over Na2S04, filtered and concentrated under reduced pressure. The resulting crude material was purified by flash chromatography (30% EtOAc in hexane) yielding tert-butyl 4-(1 -methyl- lH-pyrazol-4-yl)isoindoline-2-carboxylate (0.121 g, 0.404 mmol). LCMS: Method A, 2.335 min, MS: ES+ 300.53; NMR (400 MHz, DMSO-d6) delta ppm 8.03 (d, J=11.2 Hz, 1H), 7.78 (d, J=20.4 Hz, 1H), 7.43 – 7.49 (m, 1H), 7.31 (t, J=7.2 Hz, 1H), 7.19 (t, J=7.6 Hz, 1H), 4.69 (s, 2 H), 4.62 (d, J=11.2 Hz, 2 H), 3.90 (s, 3 H), 1.48 (s, 9 H).

The synthetic route of 1035235-27-8 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

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. 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below. Product Details of 1035235-27-8

tert-Butyl 4-bromoisoindoline-2-carboxylate (163 mg, 0.548 mmol), methyl 3-hydroxybenzoate (100 mg, 0.657 mmol), di-tert-butyl(2?,4?,6?-triisopropyl-[1,1?-biphenylj-2-yl)phosphine (23 mg, 0.055 mmol), palladium(II) acetate (12 mg, 0.055 mmol) and potassium phosphate (233 mg, 1.10 mmol) were added to a vial, which was then evacuated and back-filled with argon three times. Degassed toluene (1.8 mL) was added. The reaction mixture was stirred at 115 C for 16 h. The reaction mixture wasdiluted with DCM, filtered, and purified by flash chromatography to give 231A (55 mg,27%) as a colorless oil. MS(ESI) m/z 269.9 (M-Boc+H).

The synthetic route of 1035235-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; SMALLHEER, Joanne, M.; SHAW, Scott, A.; HALPERN, Oz, Scott; HU, Carol, Hui; KICK, Ellen, K.; (311 pag.)WO2017/40449; (2017); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Application of 1035235-27-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1035235-27-8 name is tert-Butyl 4-bromoisoindoline-2-carboxylate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 136 r(S)-1-(2.4-Difluoro-3-phenoxy-phenyl)-propy|1-(2,3-dihydro-1 H-isoindol-4-yl)-am hydrochlorideStep 1 A solution of Key Intermediate 1 (50 mg, 0.19 mmol), fe -butyl 4- bromoisoindoline-2-carboxylate (57 mg, 0.19 mmol) and sodium fe -butoxide (26 mg, 0.27 mmol) in dioxane (1 ml) was degassed by bubbling through nitrogen for 5 mins. Tris(dibenzylideneacetone)dipalladium (0) (5 mg) and 2,2′-bis(diphenylphosphino)-1 ,1 ‘- binapthyl (5 mg) were added and the reaction mixture was heated to 120 C for 20 mins under microwave irradiation. The mixture was partitioned between sat. sodium hydrogen carbonate and ethyl acetate. The organic fractions were washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by preparative hplc to give 4-[(S)-1-(2,4-difluoro-3-phenoxy-phenyl)-propylamino]-1 ,3-dihydro-isoindole-2- carboxylic acid tert-butyl ester (23 mg) as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, tert-Butyl 4-bromoisoindoline-2-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ASTEX THERAPEUTICS LIMITED; WOODHEAD, Andrew, James; CHESSARI, Gianni; BESONG, Gilbert, Ebai; CARR, Maria, Grazia; HISCOCK, Steven, Douglas; O’BRIEN, Michael, Alistair; REES, David, Charles; SAALAU-BETHELL, Susanne, Maria; WILLEMS, Hendrika, Maria, Gerarda; THOMPSON, Neil, Thomas; WO2013/64538; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Reference of 1035235-27-8, These common heterocyclic compound, 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate, 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.

Step a. A suspension of 3-amino-N-methylisoquinoline-6-carboxamide TFA salt (Intermediate 6, 0.40 g, 1.262 mmol), tert-butyl 4-bromoisoindoline-2-carboxylate (Intermediate 1, 0.15 g, 0.505 mmol), and potassium tert-butoxide (0.28 g, 2.525 mmol) in toluene (10 ml) was degassed with nitrogen for 10 min at rt. BetaIotaNuAlphaRho (0.047 g, 0.050 mmol) and Pd2(dba)3 (0.032 g, 0.050 mmol) were added to the reaction mixture at rt. The reaction mixture was heated at 105C for 2 h. The resulting reaction mixture was cooled to rt, poured into water (20 ml) and extracted with EtOAc (2 x 40 ml). The combined organic phase was dried over Na2S04, filtered and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (4% MeOH in DCM) yielding tert-butyl 4-((6-(methylcarbamoyl)isoquinolin-3-yl)amino)isoindoline-2-carboxylate (0.135 g, 0.322 mmol). LCMS: Method A, 2.278 min, MS: ES+ 419.5.

The synthetic route of 1035235-27-8 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

Synthetic Route of 1035235-27-8, 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. 1035235-27-8, name is tert-Butyl 4-bromoisoindoline-2-carboxylate belongs to indolines-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A mixture of tert-butyl 4-bromoisoindoline-2-carboxylate (1.00 g, 3.37mmol), 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1 ,3,2-dioxaborolane) (1.03 g, 4.04 mmol), AcOK (661 mg, 6.74 mmol) and Pd(dppf)C12 (50.0 mg) in dioxane (20 mL) was stirred at 90C lbr 16 h under the nitrogen atmosphere. After cooling down to 20C and LCMS showed the reaction was complete, the mixture was filtered and the filtrate was concentrated under reduced pressure to get the title compound (1.2 g, yield 103%) as a brown solid, which was directly to the next step without further purification ?HNMR(CDC13, 400 MHz) oe 7.69 (d, J 7.2 Hz, 1 H) 7.36-7.27 (m, 2 H) 4.87-4.63 (m, 4 H) 1.52 (s, 9 H) 1.31 (s, 12 H).

The synthetic route of tert-Butyl 4-bromoisoindoline-2-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KADMON CORPORATION, LLC; KIM, Ji-in; LIU, Kevin; POYUROVSKY, Masha; LU, Dan; ZHU, Zhenping; WO2015/54317; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem