Category: 64169-34-2

64169-34-2, 5-Bromoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A three-neck 5 L round bottomed flask equipped with a stir bar, firestone valve, thermocouple, condenser and heating mantle was charged with tri-t-butyl phosphonium tetrafluoroborate (500 mg, 1.72 mmol), palladium (II) acetate (250 mg, 1.1 mmol) and 5-bromo-2-benzofuran-1(3H)-one (100 g, 470 mmol). DMF (1.88 L) was added to the flask, and the mixture was degassed three times by alternating vacuum and nitrogen purge. Commercially available bromo(1,3-dioxolan-2-ylmethyl)zinc solution (1.03 L, 516 mmol) was added via cannula and the mixture was again degassed three times. The mixture was then heated at 85 C. for 5 hr. Analysis by HPLC-MS indicated the reaction was not complete. The mixture was stirred at 85 C. for 5 more h. The mixture was then cooled to return to room temperature for overnight. 2-MethylTHF (2 L) and brine were added, and the mixture was stirred for 5 min. The layers were separated and the aqueous layer was extracted again with 2-methylTHF. The organic layers were combined, washed three times with brine (4 L each), dried over MgSO4, filtered, and concentrated. The crude product was purified by flash chromatography (1.5 kg silica cartridge), eluting with 0-20% ethyl acetate in dichloromethane to afford the title compound. MS [M+H]+=221.

64169-34-2, 64169-34-2 5-Bromoisobenzofuran-1(3H)-one 603144, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; Merck Sharp & Dohme Corp.; Biswas, Dipshikha; Ding, Fa-Xiang; Dong, Shuzhi; Gu, Xin; Jiang, Jinlong; Pasternak, Alexander; Suzuki, Takao; Vacca, Joseph; Xu, Shouning; (81 pag.)US2017/37037; (2017); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

64169-34-2, 5-Bromoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

2-Benzyl-4-bromo-benzoic acid (239):239 Ste p l3,5-Dibromo-3H-isobenzofuran-l-one (B3): The mixture of 5-bromo-3H-isobenzofuran-l- one (A3) (51.5g, 242 mmol) in bromobenzene (10OmL) is heated to 158C. Bromine (18.8mL, 363 mmol) is added dropwise to the mixture over 2h. The mixture is stirred for another 30 min. at 158C. The bromobenzene is removed by distillation under vacuum. The residue is vacuum dried 1 hour at 1200C to yield a black crystalline residue. Recrystallization: The residue is193 dissolved in hot isopropyl ether (30OmL). Activated charcoal (1 g) is added, stirred and filtered while hot. The filtrate is cooled in ice-water bath (00C) over night. The solid is filtered and is rinsed with cold isopropyl ether (2 x 1OmL) and vacuum dry over KOH (KOH) to yield 3,5-dibromo-3H-isobenzofuran-l-one (B3) (38g, 54%, mp: 1000C).

64169-34-2, 64169-34-2 5-Bromoisobenzofuran-1(3H)-one 603144, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; SANOFI-AVENTIS; WO2008/151211; (2008); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.64169-34-2,5-Bromoisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

Step 2. Racemic tert-butyl (trans-2-((1-oxo-1,3-dihydroisobenzofuran-5-yl)oxy)cyclobutyl)carbamate (30-3a) To 5-bromoisobenzofuran-1(3H)-one (19-1a, 300 mg, 1.41 mmol), racemic trans-tert-butyl-3-hydroxycyclopentyl)carbamate (30-2a, 440 mg, 2.35 mmol), NiCl2(glyme) (15.5 mg, 0.070 mmol), dtbbpy (18.9 mg, 0.070 mmol), and Ir[(dF(CF3)ppy)2dtbbpy]PF6 (15.8 mg, 0.014 mmol) under an atmosphere of nitrogen was added MeCN (4.7 mL) and 2,2,6,6-tetramethylpiperidine (40-2, 286 mul, 1.69 mmol) and the resulting mixture was stirred vigorously for 16 hours under irradiation of blue LED light at room temperature. The reaction mixture was filtered through a short pad of Celite and concentrated to dryness. The crude material was purified by silica gel chromatography eluting with 0% to 100% EtOAc (with 1% Et3N modifier) in heptane to afford 30-3a (445 mg, 1.39 mmol, 99% yield) as a white solid. MS [M-tBu+H]+=320.3., 64169-34-2

The synthetic route of 64169-34-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Novartis AG; ADCOCK, Claire; BONAZZI, Simone; CERNIJENKO, Artiom; LAM, Philip; LINKENS, Kathryn Taylor; MALIK, Hasnain Ahmed; THOMSEN, Noel Marie-France; VISSER, Michael Scott; US2020/17461; (2020); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

64169-34-2, 5-Bromoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-benzofuran-l(3H)-one To a microwave tube containing a stir bar was added 5-bromo-2-benzofuran-l (3H)-one (0.10 g, 0.47 mmol), Bis(pinacolato)diboron (0.12 g, 0.47 mmol), bis(diphenylphosphino)palladium(II) (0.010 g, 0.014 mmol), potassium acetate (0.14 g, 1.4 mmol) and anhydrous toluene (10 mL). The resulting mixture was capped and heated at 80 C for 2 h. The reaction mixture was diluted with benzene and washed successively with water and brine. The organic layer was then dried (Na2S04), filtered, and concentrated. The resulting residue was purified by silica gel column chromatography (hexanes/EtOAc = 1/1) to provide 5- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-2-benzofuran-l(3H)-one. LC/MS: [(M+l)]+ =261.

64169-34-2, The synthetic route of 64169-34-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; WO2013/39802; (2013); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.64169-34-2,5-Bromoisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

5-Bromoisobenzofuran-l(3H)-one (1.0 g, 4.69 mmol), NBS (835 mg, 4.69 mmol), and carbon tetrachloride (15.6 mL) were heated to reflux in a 50 mL flask carrying a reflux condenser equipped with a drying tube. The reaction mixture was exposed to light of an ordinary 100-W unfrosted light bulb placed 6-8″ from the flask. After 30 min, the succinimide was removed by filtration and the filtrate was concentrated under atmospheric pressure to give crude 3,5-dibromoisobenzofuran-l(3H)-one. To 3,5-dibromoisobenzofuran-l(3H)-one was added methanol directly to afford 5-bromo-3-methoxyisobenzofuran-l(3H)-one. LC/MS: [(M+l)]+ = 244

64169-34-2, 64169-34-2 5-Bromoisobenzofuran-1(3H)-one 603144, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; PIO, Barbara; CHOBANIAN, Harry, R.; SHI, Zhi-Cai; DONG, Shuzhi; GUO, Yan; WALSH, Shawn, P.; GUO, Zhiqiang; FERGUSON, Ronald, D.; CATO, Brian; (114 pag.)WO2016/60941; (2016); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

64169-34-2, 5-Bromoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[0338j Lithium hydroxide (3.45 g, 70.42 mmol, 3.0 equiv) was added at room temperature over several minutes to a solution of 5-bromophthalide (5.0 g, 23.47 mmol, 1.0 equiv) in a 2:1:1 solution of THF/MeOH/ H20 (80 mL) and the reaction mixture was stirred at room temperature for 16 h. After removal of the solvent, the residue was diluted with water (100 mL), adjusted to pH = 3 with HC1 (2 N) and extracted with EtOAc (100 mL x 3). The organic layers were collected, dried (Na2SO4), filtered, and concentrated via rotary evaporator to give title product (3.47 g, yield: 94%) as a white solid, which was used in the next step withoutfurther purification. ESI-MS (M+H) : 231.1. ?H NMR (400 MHz, CD3OD) (5: 7.88-7.86 (m, 2H), 7.45 (dd, J= 8.4, 2.0 Hz, 1H), 4.90 (s, 2H).

64169-34-2, The synthetic route of 64169-34-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian, T.; MA, Bin; CHAN, Timothy, Raymond; SUN, Lihong; ZHANG, Lei; KUMARAVEL, Gnanasambandam; LYSSIKATOS, Joseph, P.; KOCH, Kevin; MIAO, Hua; WO2015/89337; (2015); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.64169-34-2,5-Bromoisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

5-Bromophthalide (50g, 235 mmol), potassium vinyl trifluoroborate (62.9 g, 469 mmol), and PdCl2(dppf)-CH2Cl2 Adduct (9.58 g, 11.7 mmol) were added to ethanol (500 mL) then TEA (65.4 mL, 469 mmol) was added. The reaction mixture was degassed then heated at reflux for 8 h. The reaction was worked up by diluting with ethyl acetate and washing with brine twice. The organic layer was dried and evaporated to dryness. The crude product was purified by MPLC (silica, 600g column) with 25% EtOAc/hexane (3 L) then with 30% EtOAc/Hexane (2 L) to yield the title compound., 64169-34-2

As the paragraph descriping shows that 64169-34-2 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; PIO, Barbara; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; WALSH, Shawn; WO2013/90271; (2013); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

64169-34-2, 5-Bromoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 35: Synthesis of 5-(5-Fluoro-4-hydroxymethyl-pyridin-3-yl)-3H-isobenzofuran- 1 -one Step 1 : 5-(4,4,5,5-Tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-3H-isobenzofuran-1-one (35a) A 100 round bottom flask was charged with 5-bromo-3H-isobenzofuran-1-one (750 mg, 3.52 mmol), bis(pinacolato)diboron (894 mg, 3.52 mmol), potassium acetate (691 mg, 7.04 mmol) and 1,4-dioxane (25 mL). The reaction mixture was evacuated and flushed with N2 twice followed by addition of PdClz(dppf).CH2CI2 adduct (144 mg, 0.176 mmol). The reaction was stirred under N2 at 100 “C overnight. The reaction mixture was cooled to room temperature, diluted with ethyl acetate and washed with water twice. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude was purified using silica gel flash chromatography employing heptane-ethyl acetate(7:3) to afford 5-(4,4,5,5-tetramethyl- [1 ,3,2]dioxaborolan-2-yl)-3H-isobenzofuran-1-one., 64169-34-2

64169-34-2 5-Bromoisobenzofuran-1(3H)-one 603144, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; ALLAN, Martin; CHAMOIN, Sylvie; HU, Qi-Ying; IMASE, Hidetomo; PAPILLON, Julien; WO2011/61168; (2011); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

64169-34-2, 5-Bromoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step A: 5-(l,3-Dioxolan-2-ylmethyl)-2-benzofuran-l(3H)-one: A three-neck 5L round bottomed flask equipped with a stir bar, firestone valve, thermocouple, condenser and heating mantle was charged with tri-t-butyl phosphonium tetrafluoroborate (500 mg, 1.72 mmol), palladium (II) acetate (250 mg, 1.1 mmol) and 5-bromo-2-benzofuran-l(3H)-one (100 g, 470 mmol). DMF (1.88 L) was added to the flask, and the mixture was degassed three times by alternating vacuum and nitrogen purge. Commercially available bromo(l,3-dioxolan-2- ylmethyl)zinc solution (1.03 L, 516 mmol) was added via canula and the mixture was again degassed three times. The mixture was then heated at 85 C for 10 h. The mixture was then allowed to return to room temperature for overnight. 2-methylTHF (2L) and brine were added, and the mixture was stirred for 5 min. The layers were separated and the aqueous layer was extracted again with 2-methylTHF. The organic layers were combined, washed three times with brine (4L each), dried over MgS04, filtered, and concentrated. The crude product was purified by flash chromatography (1.5 kg silica cartridge), eluting with 0-20% ethyl acetate in dichloromethane to afford 5-(l,3-dioxolan-2-ylmethyl)-2-benzofuran-l(3H)-one., 64169-34-2

As the paragraph descriping shows that 64169-34-2 is playing an increasingly important role.

Reference£º
Patent; MERCK SHARP & DOHME CORP.; DONG, Shuzhi; PASTERNAK, Alexander; GU, Xin; FU, Qinghong; JIANG, Jinlong; DING, Fa-Xiang; TANG, Haifeng; DEJESUS, Reynalda, K.; SUZUKI, Takao; WO2015/100147; (2015); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

64169-34-2, 5-Bromoisobenzofuran-1(3H)-one is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 13:A solution of 5-bromophthalide (1.Og, 4.7 mmol, 1.0 equiv) and NBS (850 mg, 4.7 mmol, 1.0 equiv) in carbon tetrachloride (15 mL) was treated with AIBN (50 mg, cat.) and heated to reflux overnight. The hot reaction mixture was filtered and the filtrate concentrated to a yellowish solid (1.38g, quant.). Crude H NMR indicated this material contained ca. 80% of the desired 3,5-dibromophthalide, and it was carried on without further purification. An aliquot of this crude material (250 mg, 0.69 mmol, 1.0 equiv) in 95% ethanol (6 mL) was treated with phenelzine sulfate (175 mg, 0.75 mmol, 1.1 equiv) and NaHCO3 (250 mg, 2.8 mmol, 4.0 equiv). After stirring overnight at ambient temperature, the reaction mixture was diluted with diethyl ether, washed with dilute NaOH, dilute HCl, and saturated NaHCO3, then dried over Na2SO4 and concentrated. Purification of the residue using flash silica gel chromatography (gradient of 3- 12% ethyl acetate/hexanes) provided 6-bromo-2-phenethyl-l-phthalazinone (147 mg, 0.45 mmol, 65%) as a white solid. This crude phthalazinone (147 mg, 0.45 mmol) was converted, via Methods 1 and 2, to compound 13 (81 mg, 62%) which was isolated as a white solid. [M-H]- = 293.1 m/z. Activity: A, 64169-34-2

As the paragraph descriping shows that 64169-34-2 is playing an increasingly important role.

Reference£º
Patent; INFINITY PHARMACEUTICALS, INC.; CASTRO, Alfredo, C.; GROGAN, Michael, J.; SNYDER, Daniel, A.; WO2010/118155; (2010); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem