Tag: 13391-28-1

Analyzing the synthesis route of 13391-28-1

As the paragraph descriping shows that 13391-28-1 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13391-28-1,5-Methoxybenzofuran,as a common compound, the synthetic route is as follows.

Step A: Preparation of 5-Methoxy-2-sulfamoylbenzo[b]furan A solution of 5-methoxybenzo[b]furan (10.8 g, 73 mmol) in 100 ml of dry THF was cooled to -65 C. A 1.6M solution of n-butyllithium in hexane (50 ml, 80 mmol) was added rapidly, dropwise, such that the temperature did not exceed -55 C. After 15 minutes at -55 C. sulfur dioxide gas was passed into the reaction flask until an aliquot removed from the flask and dissolved in water was no longer basic to pH paper. Hexane (100 ml) was added to precipitate the product. After warming to room temperature, the product was isolated by filtration. The crude product was dried under low vacuum for 18 hours at room temperature, yielding 15.6 g (98%) of a tan powder. The dry sulfinate salt so obtained was suspended in 150 ml CH2 Cl2 and cooled to 5 C. prior to adding 10.7 g of N-chlorosuccinimide (80 mmol). Stirring was continued for 15 minutes at 5 C. and the cooling bath was removed. After an additional 15 minutes the suspension was filtered through a pad of filter aid. Evaporation of the solvent furnished 17.2 g of sulfonyl chloride as a brown solid. This material was dissolved in 50 ml of dry acetone and added over a 1 minute period to a chilled (5 C.) stirring solution of 15 ml NH4 OH in 150 ml acetone. After 30 minutes the solvent was evaporated. The residue was partitioned between water and ethyl acetate. The organic phase was washed with brine and dried (Na2 SO4). Evaporation left 17.2 g of brown solid. The pure compound was obtained by recrystallization from dichloroethane; m.p. 119-120 C. Analysis calculated for C9 H9 NO4 S: C, 47.57; N, 6.16; H, 3.99; Found: C, 47.52; N, 6.14; H, 4.02. ‘H NMR (d6 -acetone) 7:7.50 (1H, d, J=9), 7.30 (1H, s), 7.25 (1H, d, J=3), 7.1 (1H, dd, J=9, 3), 3.83 (3H, s).

As the paragraph descriping shows that 13391-28-1 is playing an increasingly important role.

Reference£º
Patent; Merck & Co., Inc.; US4544667; (1985); A;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

Some tips on 13391-28-1

The synthetic route of 13391-28-1 has been constantly updated, and we look forward to future research findings.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13391-28-1,5-Methoxybenzofuran,as a common compound, the synthetic route is as follows.

To a stirred solution of 5-methoxybenzofuran (1) (0.50 g, 3.38 mmol) in dichloromethane (15 mL), boron tribromide (16.87 mL, 16.87 mmol, IM solution in dichloromethane) was added slowly at O0C. The reaction mixture was warmed to room temperature and stirred for 4 hours. The reaction mixture was then cooled to O0C, quenched with aqueous saturated NaHCO3 solution and extracted with dichloromethane (3 x 50 mL). The combined organic extracts were washed with brine (25 mL), dried over Na2SO4, and concentrated under reduced pressure to give compound (2) as an off white solid (300 mg) which was used in the next step without further purification. 1H NMR (400 MHz, CHLOROFORM-J) delta: 7.59 (d, J=I.95 Hz, 1 H), 7.35 (d, J=8.59 Hz, IH), 7.00 (d, J=2.73 Hz, IH), 6.80 (dd, 8.59, 2.74 Hz, IH), 6.67 (m, IH), 4.66 (s, IH)

The synthetic route of 13391-28-1 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; BJOeRK, Seth; DELISSER, Vern; JOHNSTROeM, Peter; NILSSON, Nils Anders; RUDA, Katinka; SCHOU, Per Magnus; SWAHN, Britt-Marie; WO2010/24769; (2010); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

Analyzing the synthesis route of 13391-28-1

As the paragraph descriping shows that 13391-28-1 is playing an increasingly important role.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.13391-28-1,5-Methoxybenzofuran,as a common compound, the synthetic route is as follows.

To 5-methoxybenzofuran (188 mg, 1.269 mmol) in THF (4.0 mL) at -78 C wasadded 1.6 N n-BuLi in hexanes (1.190 mL, 1.903 mmol) dropwise. The solution became slightly yellow. The reaction mixture was stirred at -78 C for 20 mm, followed by addition of triisopropyl borate (0.737 mL, 3.17 mmol). After 30 mm stirring at -78 C, the cooling bath was removed and the stirring was continued at room temperature for 1.5h. The reaction mixture was diluted with EtOAc, quenched with 3.0 mL of 1.0 N HC1.After stirring at room temperature for 25 mm, the organic layer was collected, washedwith brine and dried over sodium sulfate. After evaporation of solvent, the cmde product was dissolved in a small amount of chloroform/a drop of MeOH and charged to a 4 g silica gel cartridge which was eluted with hexanes for 2 mm., then a 10 mm gradient from 0% to 60%. The desired fractions were combined, concentrated and lyophilized to giveIntermediate 2A (170 mg, 0.886 mmol, 69.8 % yield) as a white solid. ?H NMR (500MHz, methanol-d4) oe 7.41 (d, J=9. 1 Hz, 1H), 7.30 (s, 1H), 7.14 (d, J2.5 Hz, 1H), 6.96 (dd, J=8.9, 2.6 Hz, 1H), 3.84 (s, 3H); LC-MS: method A, RT = 1.45 mm, MS (ESI) m/z: 149.0 (M-B(OH)2)t

As the paragraph descriping shows that 13391-28-1 is playing an increasingly important role.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem

Downstream synthetic route of 13391-28-1

13391-28-1 5-Methoxybenzofuran 25943, abenzofuran compound, is more and more widely used in various.

13391-28-1, 5-Methoxybenzofuran is a benzofuran compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

j0379j 2.5 M n-butyllithium in hexanes (2.8 mE, 7.00 mmol) was added slowly to a solution of 5-methoxy-i-benzofuran(1.0 g, 6.75 mmol) in dry tetrahydrothran (15 mL) at -78 C under a nitrogen atmosphere. After 1 hour stirring at -78 C, triisopropylborate (3.12 mL, 13.5 mmol) was added drop-wise and the mixture stirred for 30 minutes at -78 C. The dry ice bath was removed, 2 M aqueous hydrochloric acid (20 mL) was added and the mixture warmed to room temperature whilst stirring overnight. The reaction mixture was poured into waler (25 mL) and extracted with diethyl ether (3 x 20 mL). The combined organics were washed with brine (20 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure. Dichloromethane (20 mL) was added and the mixture sonicated for 10 minutes. The minimum amount of methanol (ca. 1 mL) was added to ffilly dissolve the solids and the solution sonicaled for 10 minutes. Heptane (20 mL) was added and the precipitated solids collected by vacuum filtration and allowed to dry under vacuum for 2 hours to give the title compound 476 mg (37% yield) as a white solid. On NMR (500 MHz, DMSO) 8.53 (s, 2H), 7.46 (d, J= 8.94 Hz, IH), 7.39 (s, lH), 7.19 (d, J= 2.51 Hz, 1H), 6.93 (dd, J= 2.60,8.92 Hz, 1H), 3.78 (s, 3H).

13391-28-1 5-Methoxybenzofuran 25943, abenzofuran compound, is more and more widely used in various.

Reference£º
Patent; CHDI FOUNDATION, INC.; DOMINGUEZ, Celia; WITYAK, John; BARD, Jonathan; KISELYOV, Alex; BROWN, Christopher, John; GALAN, Sebastien, Rene Gabriel; PRIME, Michael, Edward; GILES, Paul, Richard; GADOULEAU, Elise, Luciennen Paulette; KRUeLLE, Thomas, Martin; CLARK-FREW, Daniel; JOHNSON, Peter, David; SCHAERTL, Sabine; HERRMANN, Frank; GRIMM, Steffen, Kaspar; KAHMANN, Jan, Dirk; SCHEICH, Christoph; COE, Samuel; HAYES, Sarah; (271 pag.)WO2016/33445; (2016); A1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem