Day: October 28, 2020

20699-85-8, Methyl 5-aminobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: Compound 5 A (100 mg, 0.241 mmol) and amine 12 (43.7 mg, 0.289 mmol) were dissolved in DMF (1.61 mL). EDC (69.2 mg, 0.361 mmol) was added to the solution at rt, followed by DMAP (14.70 mg, 0.120 mmol) and was stirred overnight. Water was added to the reaction mixture to precipitate the product. The resulting slurry was stirred for 15 min. The solution was filtered and the solid was dried under vacuum/N2 for 2 h to obtain compound 13 as an off white solid (127 mg, 0.231 mmol, 96% yield). LCMS = 6.408 min (8 min method). Mass observed (ESI+): 549.15 (M+H). 1H NMR (400 MHz, DMSO-76): d 1.31 (s, 6H), 1.46 (s, 9H), 2.45 (s, 3H), 3.48 (d, 7 = 6.3 Hz, 2H), 3.83 (s, 3H), 6.97 (s, 2H), 7.72 – 7.79 (m, 1H), 7.92 (d, 7 = 8.8 Hz, 1H), 8.11 (d, 7 = 3.7 Hz, 1H), 8.31 – 8.41 (m, 2H), 8.70 (t, 7 = 6.3 Hz, 1H), 9.14 (s, 1H), 9.94 (s, 1H)., 20699-85-8

Big data shows that 20699-85-8 is playing an increasingly important role.

Reference£º
Patent; IMMUNOGEN, INC.; MILLER, Michael, Louis; SHIZUKA, Manami; CHARI, Ravi, V.J.; (312 pag.)WO2019/133652; (2019); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5381-20-4,Thianaphthene-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

5381-20-4, Synthesis of methyl 4-aminobenzoate esters 5a-d and 11a-b The synthesis of 3-[(4-methoxycarbonylphenyl)aminomethyl]benzothiophene 5a will be used as an example for the synthesis of secondary amines 5a-d and 11 a-b. Benzothiophene-3- carbaldehyde 3a (406 mg, 2.5 mmol, 1 equiv) was dissolved in ethanol (15 mL) and to this solution were added glacial acetic acid (751 mg, 12.5 mmol, 5 equiv) and methyl 4- aminobenzoate (454 mg, 3 mmol, 1 .2 equiv). This reaction mixture was stirred for one hour at refluxing conditions after which it was cooled to 0C. Sodium cyanoborohydride (471 mg, 7.5 mmol, 3 equiv) was added and the reaction mixture was allowed to warm to room temperature. After one hour the mixture was poured in to brine (15 mL) and three times extracted with EtOAc (15 mL). The combined organic fraction was thereafter three times washed with brine (15 mL), dried (MgS04), filtered and evaporated under vacuum. Purification through recrystallization from ethanol yielded 3-[(4- methoxycarbonylphenyl)aminomethyl]-benzothiophene 5a (520 mg, 1 .75 mmol, 70%) as a white powder. For secondary amine 5b a solvent mixture of ethanol/CH2CI2(1 /1 ) was used as solvent for the reaction. 5a: 3-[(4-methoxycarbonylphenyl)aminomethyl]benzothiophene 70% as white powder; recrystallization from EtOH; m.p. 127C;1H-NMR (300 MHz, CDCI3): delta = 3.84 (s, 3H); 4.48 (s(broad), 1 H); 4.58 (d, J = 5.0 Hz, 2H); 6.62 (d, J = 8.8 Hz, 2H); 7.32 (s, 1 H); 7.35-7.43, 7.73-7.81 and 7.86-7.90 (3 m, 2H, 1 H and 3H);13C-NMR (75 MHz, CDCI3): delta = 42.2, 51 .7,1 1 1 .8, 1 19.0, 121 .7, 123.2, 124.1 , 124.4, 124.8, 131 .7, 132.8, 137.8, 141 .0, 151 .7 and 167.4; IR (cm”1): v = 3379 (N H); 1685 (C=0); MS (70 eV): m/z (%) = 296 (100) [M”- H]; HRMS (ESI)Anal. Calcd. for Ci7H14N02S 296.0751 [M”- H], Found 296.0760.

As the paragraph descriping shows that 5381-20-4 is playing an increasingly important role.

Reference£º
Patent; UNIVERSITEIT GENT; DE VREESE, Rob; D’HOOGHE, Matthias; (52 pag.)WO2016/110541; (2016); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

20532-33-6, 5-Chlorobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation 22 Preparation of 3-bromo-5-chlorobenzo[b]thiophene A solution of bromine (0.31 g, 1.95 mmol) in 1.0 ml glacial acetic acid was added to a stirred solution of 5-chlorobenzo[b]thiophene (0.300 g, 1.77 mmol)in glacial acetic acid (1.0 ml) under nitrogen atmosphere. The reaction was heated to 50 C. for 4 hours, the volatiles removed under reduced pressure, the residue diluted in methylene chloride, washed with aq. sodium bicarbonate and with brine and dried over sodium sulfate. Evaporation gave 0.335 g (76%) of a tan solid. mp 85-86C., FDMS m/e=249 (M+2)., 20532-33-6

20532-33-6 5-Chlorobenzothiophene 11309754, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Patent; Eli Lilly and Company; US5741789; (1998); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20699-85-8,Methyl 5-aminobenzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.

A mixture of 500 mg of methyl 5-aminobenzo[b]thiophene-2-carboxylate, 320 mg of acetic anhydride, 623 mgof diisopropylethylamine, and 10 ml of dichloromethane was stirred for 4 hours at room temperature. The reaction mixturewas washed with an aqueous saturated sodium hydrogen carbonate solution and saturated saline, dried over magnesiumsulfate, and concentrated under reduced pressure. The residues were subjected to silica gel column chromatography,thereby obtaining 449 mg of methyl 5-(acetylamino)benzo[b]thiophene-2-carboxylate., 20699-85-8

As the paragraph descriping shows that 20699-85-8 is playing an increasingly important role.

Reference£º
Patent; Sumitomo Chemical Company Limited; MUKUMOTO, Fujio; TAMAKI, Hiroaki; KUSAKA, Shintaro; IWAKOSHI, Mitsuhiko; EP2926660; (2015); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1423-61-6,7-Bromobenzo[b]thiophene,as a common compound, the synthetic route is as follows.

A Grignard reagent was prepared using 7-bromobenzo-[b] thiophene (1.0 g), magnesium (0.13g), a catalytic amount of iodine and tetrahydrofuran (3 mL) according to the general method. To the Grignard reagent solution was added a solution of 4-methylbenzaldehyde (0.62 g) in tetrahydrofuran (5 mL) at 0C under an argon atmosphere. The reaction mixture was stirred at room temperature overnight and a saturated ammonium chloride aqueous solution was added to the mixture. The mixture was extracted with diethyl ether, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran). Further purification by column chromatography on silica gel (eluent; n-hexane/ethyl acetate = 6/1) gave the title compound (0.68 g) as yellow oil. 1H-NMR (CDCl3) delta ppm: 2.32 (3H, s), 2.38 (1H, d, J=3.6Hz), 6.11 (1H, d, J=3.4Hz), 7.10-7.20 (2H, m), 7.30-7.45 (5H, m), 7.45-7.50 (1H, m), 7.70-7.80 (1H, m)

1423-61-6, 1423-61-6 7-Bromobenzo[b]thiophene 12045538, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Patent; Kissei Pharmaceutical Co., Ltd.; EP1724277; (2006); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1127-35-1,Benzo[b]thiophene-3(2H)-one 1,1-Dioxide,as a common compound, the synthetic route is as follows.

To a stirred solution of N-(phenylthio)-succinamide (20 mg, 0.10 mmol) in 3 mL of 3:1 methanol-HEPES buffer (50 mM HEPES, 100 mM NaCl and 1 mM EDTA) was added C (19 mg, 0.11 mmol) and the reaction stirred at 24 C for 4 h. The solid formed during the reaction was collected on a sintered glass funnel and washed with ice cold water (2 * 2 mL) to afford 7 as a white powder (17.5 mg, 91% yield) mp: 134-136 C Rf = 0.70 (30% ethyl acetate/hexanes). 1H NMR (CDCl3, 500 MHz) delta 7.95 (d, J = 7.5 Hz, 1H), delta 7.86-7.89 (m, 1H), delta 7.79 (d, J = 7.5 Hz, 1H), delta 7.71-7.74 (m, 1H), delta 7.65-7.67 (m, 4H), delta 7.38-7.42 (m, 2H), delta 7.38 (t, J = 7.5 Hz, 4H); 13C NMR (CDCl3, 125 MHz) delta 183.2, 142.8, 137.0, 136.7, 134.3, 131.0, 130.5, 128.9, 127.6, 125.4, 122.3, 82.9; IR (cm-1) 3056, 2982, 1724, 1328, 1270, 1160, 739, 702; HRMS (ESI-TOF, [M+H]+) m/z calcd for C20H15O3S3 399.0183, found 399.0169., 1127-35-1

As the paragraph descriping shows that 1127-35-1 is playing an increasingly important role.

Reference£º
Article; Parsons, Zachary D.; Ruddraraju, Kasi Viswanatharaju; Santo, Nicholas; Gates, Kent S.; Bioorganic and Medicinal Chemistry; vol. 24; 12; (2016); p. 2631 – 2640;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.20699-85-8,Methyl 5-aminobenzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.

Compound 60 (29 mg, 0.118 mmol) and compound 61 (37 mg, 0.177 mmol) were dissolved in DMF (1.18 mL). EDC (34 mg, 0.177 mmol) was added to the reaction mixture, followed by DMAP (14 mg, 0.118 mmol). The reaction was stirred at rt for 2 h. The solution was diluted with water and EtOAc and the layers were separated. The organic layer was washed with sat’d NH4Cl, water (3x), dried over Na2S04, filtered and concentrated. The crude residue was purified by RPHPLC (Cl 8 column, ACN/H20) to obtain compound 62 as a solid (10 mg, 0.023 mmol, 20% yield). UPLCMS = 1.69 min (2.5 min method). Mass observed (ESI+): 436.3 (M+H)., 20699-85-8

As the paragraph descriping shows that 20699-85-8 is playing an increasingly important role.

Reference£º
Patent; IMMUNOGEN, INC.; MILLER, Michael, Louis; SHIZUKA, Manami; CHARI, Ravi, V.J.; (312 pag.)WO2019/133652; (2019); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

95-15-8, Thianaphthene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

95-15-8, General procedure: To a stirred, cooled (0 C) solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2-3 mL) were successively added BuLi (about 1.6 M hexanes solution, 1.5 mmol) and, 5 min later, ZnCl2?TMEDA14 (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0 C before introduction of the substrate (1.0 mmol) at 0-10 C. After 2 h at room temperature, a solution of I2 (0.38 g,1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before addition of an aqueous saturated solution of Na2S2O3(4 mL) and extraction with AcOEt (3 20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. To the crude iodide were added Cs2CO3(0.65 g, 2.0 mmol), Cu powder (13 mg, 0.20 mmol), the azole (1.5 mmol) and MeCN (5 mL) and the resulting mixture was heated under reflux for 24 h. Filtration over Celite, washing with AcOEt,removal of the solvent and purification by chromatography on silica gel (the eluent is given in the product description) led to the compound described below.

95-15-8 Thianaphthene 7221, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Article; Hedidi, Madani; Bentabed-Ababsa, Ghenia; Derdour, Aicha; Roisnel, Thierry; Dorcet, Vincent; Chevallier, Floris; Picot, Laurent; Thiery, Valerie; Mongin, Florence; Bioorganic and Medicinal Chemistry; vol. 22; 13; (2014); p. 3498 – 3507;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4923-87-9,5-Bromobenzothiophene,as a common compound, the synthetic route is as follows.

General procedure: To a 10 mL round-bottom flask were added Cat.III (3.2 mg, 0.005 mmol, 2 mol %), Ag2O (116 mg, 0.5 mmol, 2 equiv), benzoquinone (14 mg, 0.125 mmol, 0.5 equiv), Cs(tfa) (64 mg, 0.25 mmol, 1 equiv.), benzothiophene/benzofurans (0.25 mmol, 1 equiv), aryl MIDA boronate ( 0.375 mmol, 1.5 equiv), and 15% H2O and 2% CF3SO3H of TFA (1 mL). The reaction mixture was stirred at 30-50 C for 20 h. The suspension was cooled to room temperature and extracted with dichloromethane (3 ¡Á 10 mL). The combined organic layers were washed with 20% aqueous NaHCO3 solution (40 mL). After evaporation of the solvent the crude product was purified by chromatography on silica gel to give the desired product.

4923-87-9, 4923-87-9 5-Bromobenzothiophene 2776578, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Article; Wang, Zhiwei; Li, Yabo; Yan, Beiqi; Huang, Mengmeng; Wu, Yangjie; Synlett; vol. 26; 4; (2015); p. 531 – 536;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.5381-20-4,Thianaphthene-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

Thianaphthene-3-carboxaldehyde (1.62 g, 10.0 mmol) was dissolved in anhydrous ethanol (50 mL). Sulfamide (4.0 g, 42 mmol) was added and the mixture was heated to reflux for 16 hours. The mixture was cooled to room temperature. Sodium borohydride (0.416 g, 11.0 mmol) was added and the mixture was stirred at room temperature for three hours. The reaction was diluted with water (50 mL) and extracted with chloroform (3*75 mL). The extracts were concentrated and chromatographed (5% methanol in DCM) to yield the title compound as a white solid. 1H NMR (DMSO-d6): delta 7.98 (1H, dd, J=6.5, 2.3 Hz), 7.92 (1H, dd, J=6.6, 2.4 Hz), 7.62 (1H, s), 7.36-7.45 (2H, m), 7.08 (1H, t, J=6.3 Hz), 6.72 (2H, s), 4.31 (2H, d, J=6.3 Hz)., 5381-20-4

As the paragraph descriping shows that 5381-20-4 is playing an increasingly important role.

Reference£º
Patent; Abdel-Magid, Ahmed F.; Mehrman, Steven J.; US2006/270856; (2006); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem