Tag: M.W:200-300

1423-61-6, 7-Bromobenzo[b]thiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Preparation 2; Benzo[/?]thiophene-7-boronic acid; Combine 7-bromobenzo[?]thiophene (300 g, 1.41 mmol) and triisopropylborate (403.6 g, 2.15 mmol) in anhydrous tetrahydrofuran (THF) (4000 mL) in a 12-L Morton flask fitted with a mechanical stirrer and cool under nitrogen in a dry-ice/acetone bath to – 70 0C. Add M-butyl lithium (1.6 M in hexane, 714 g, 1.68 mmol) dropwise at such a rate as to keep the internal temperature less than -67.5 0C. After the addition is complete, allow the reaction mixture to stir at this temperature for 1 hour. Remove the cooling bath and slowly add 4 L of water. Next, add concentrated HCl (75 mL) until the pH of the solution is about pH=2. Allow the slurry to stir for 1 hour. Add sufficient 5 N aqueous NaOH to adjust the pH of the mixture to about pH=12. Separate the layers and save the aqueous layer. Dilute the organic layer with 4 L of methyl-tert-butyl ether and extract with 1 L of 5 N aqueous NaOH. Separate the layers. Combine the aqueous layer with the previous aqueous extract. Wash the aqueous layer with additional methyl-tert-butyl ether (4 L). Separate the layers and transfer the aqueous layers to a 12 L 3-neck round bottom flask fitted with a mechanical stirrer. Cool the solution to +5 0C with an ice-water bath. Add concentrated HCl slowly until the pH of the solution is about pH = 2. Stir the mixture for 30 min and filter off the resulting solid. Rinse the solid on the funnel twice with 2 L of water and allow to air-dry for 30 min. Place the solid in a vacuum oven at 50 0C and dry under vacuum overnight. Remove the yellow color by slurrying the dried solid with 2 L of w-heptane for 30 min. Again filter off the solid, air-dry for 30 min, and vacuum dry at 40 0C overnight to afford the title compound (188.8 g, 75 %) as a white solid. 1H NMR (400 MHz, CD3OD) delta 7.86 (d, J= 8 Hz, IH), 7.49-7.57 (m, 2H), 7.30- 7.39 (m, 2H).

1423-61-6, As the paragraph descriping shows that 1423-61-6 is playing an increasingly important role.

Reference£º
Patent; ELI LILLY AND COMPANY; WO2008/76705; (2008); 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.

To a solution of 7-bromobenzo[b]thiophene (5.0 g, 24 mmol) in diethyl ether (50 mL) at 100 C under nitrogen was added dropwise t-BuLi (1.3 mol/L, 55 mL). The mixture was stirred at – 100 C for 15 min, and dry acetone (3.6 g, 48 mmol) was added dropwise at -100 C. The mixture was stirred at -100 C for 2 hours. TLC showed the reaction was complete and the formation of two products (about 1 : 1). The reaction mixture was quenched with saturated aqueous ammonium chloride (20 mL) dropwise at 0 C, and then extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (2 chi 50 mL), dried over anhydrous sodium sulfate, concentrated in vacuo and purified by silica gel column chromatography [petroleum ether: ethyl acetate = 40: 1] to give compound B-302 (0.80 g, 34% yield, the lower spot on TLC) as a yellow oil.

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; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; KOENIG, Gerhard; MCRINER, Andrew, J.; (400 pag.)WO2016/100184; (2016); 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.4923-87-9,5-Bromobenzothiophene,as a common compound, the synthetic route is as follows.

To toluene 1.6mL solution of tert-butyl 2-(4-fluoroanilino)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 79mg were added ethanol 0.60mL, water 0.30mL, 5-bromobenzothiophene 61mg, sodium hydrogen carbonate 48mg and tetrakis(triphenylphosphine)palladium(0) 11mg at room temperature, and it was heated and refluxed for 6 hours. After the reaction mixture was cooled to room temperature, and ethyl acetate and water were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=5:1] to give tert-butyl 4-(benzothiophen-5-yl)-2-(4-fluoroanilino)benzoate. Trifluoroacetic acid 5.0mL was added to the obtained tert-butyl 4-(benzothiophen-5-yl)-2-(4-fluoroanilino)benzoate, and it was stirred at room temperature for 3 hours. The solvent was removed under reduced pressure, the obtained residue was refined by reversed-phase silica gel column chromatography [eluent; 80-100% acetonitrile/0.1% trifluoroacetic acid aqueous solution] to give 4-(benzothiophen-5-yl)-2-(4-fluoroanilino)benzoic acid 16mg of a yellow solid. 1H-NMR(DMSO-d6) delta value: 7.13(1H,dd,J=8.3,1.7Hz),7.19-7.27(2H,m),7.34-7.43(3H,m),7.52(1H,d,J=5.6Hz),7.56(1H,dd,J=8.5,1.6Hz),7 .81(1H,d,J=5.6Hz),8.00(1H,d,J=8.3Hz),8.07(1H,d,J=8.5Hz) ,8.10(1H,d,J=1.6Hz),9.66(1H,s),13.10(1H,s).

4923-87-9, The synthetic route of 4923-87-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; TOYAMA CHEMICAL CO., LTD.; EP1860098; (2007); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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

To a solution of compound IV (194 mg, 0.9 mmol) in 10 ml_ of MeOH was addedBenzyloxy acetaldehyde (0.086 ml_, 0.6 mmol) at room temperature. The resulting mixture was stirred overnight. NaCNBH3 (98 mg, 1.562 mmol) and acetic acid (1 ml_) were then added and the resulting mixture was stirred at room temperature for 2 hours. After work-up, the residue was purified on column (Hexanes: EtOAc = 4:1) to afford compound 5-(2-Benzyloxy-ethylamino)-benzo[b]thiophene-2-carboxylic acid methyl ester, 20a-1. Yield: 84%. LCMS m/z: 342 ([M+H]+)., 20699-85-8

The synthetic route of 20699-85-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; S*BIO PTE LTD; WO2006/101454; (2006); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

4923-87-9, 5-Bromobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4923-87-9

Cesium carbonate (163 mg, .05 mmol) was added to a solution of 3-hydroxy-N-(l-methyl- lH-pyrazol-3-yl)-5-{(l)S)-l-methyl-2-[(triisopropylsilyl)oxy]ethoxy}benzamide (225 mg, 0.5 mmol), bromotris (triphenylphosphine) copper1 (93 mg, 0.1 mmol) and 5- bromobenzothiophene (107 mg, 0.5 mmol) in dimethylacetamide (2.5 mL) and the stirred mixture heated at 2000C in a “Biotage Initiator” microwave for 4 hours. The mixture was cooled to ambient temperature and pressure, poured onto water (40 mL) and extracted with ethyl acetate (3 x 15 mL), the combined organic layers washed with brine, dried (MgSO4) and evaporated to a residue which was chromatographed on silica, eluting with 40% ethyl acetate in isohexane, to give the desired compound (100 mg). m/z 580 (M+Eta)+.

As the paragraph descriping shows that 4923-87-9 is playing an increasingly important role.

Reference£º
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/125972; (2006); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

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

A mixture of methyl 5-amino-l-benzothiophene-2-carboxylate (100 rug, 0.480 mmol), acid chloride (83 muL, 0.63 mmol) and NMM (64 muL, 0.58 mmol) was stirred in 2: 1 THF/CH2C12 for 12 hours at room temperature. The reaction mixture was partitioned between CH2Cl2 and sat’d NaHCO3, the organic layer was washed with sat’d NaCl, dried (Na2SO4), concentrated and finally triturated with diethyl ether to provide an off-white solid of the desired amide intermediate. The residue was then dissolved in 2:1 THF/water (3 mL), treated with LiOH (68 mg, 1.62 mmol). After stirring for 12 h at room temperature, the reaction mixture was partitioned between CH2Cl2 and 2M citric acid, the organic layer was washed with sat’d NaCl, dried (Na2SO4) and concentrated to a white solid and afforded 53 mg (42% yield, without purification) of the desired acid intermediate. The residue was dissolved in DMF (2 mL) and treated with EDC (49 mg, 0.26 mmol), HOBt (35 mg, 0.26 mmol) and 1,2-phenylenediamine (46 mg, 0.43 mmol). After stirring for 12 EPO h, the reaction mixture was partitioned between EtOAc and sat’d NaHCO3, the organic layer was dried (Na2SO4), concentrated and finally triturated with diethyl ether to provide the desired product: 1H NMR (600 MHz, DMSO-J5) delta 10.34 (s, 1 H), 9.85 (s, 1 H), 8.33 (s, 1 H), 8.21 (s, 1 H), 7.93 (d, J = 8.4 Hz, 1 H), 7.53 (d, J = 9.0 Hz, 1 H), 7.32 (m, 4 H), 7.23 {I, J = 1.2 Hz, 1 H), 7.13 (d, J = 7.8 Hz, 1 H), 6.94 (t, J = 7.8 Hz, 1 H), 6.75 (d, / = 7.8, Hz, 1 H), 6.57 (t, J = 7.8, Hz, 1 H), 4.95 (s, 2 H), 3.66 (s, 2 H); MS: cal’d 402 (MH+), exp 402 (MH+).

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

Reference£º
Patent; MERCK & CO., INC.; ATON PHARMA, INC.; WO2006/115845; (2006); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

4923-87-9,4923-87-9, 5-Bromobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of5-bromobenzo[b]thiophene (10.0 g, 47 mmol) and 1-octyne (6.20 g, 56 mmol) in dryTHF (80 mL) were added Pd(PPh3)4 (2.7 g, 2.3 mmol), copper(I) iodide (0.45 g, 2.4mmol), and triethylamine (15 mL). The mixture was stirred overnight at 60 C.After cooling to room temperature, the reaction mixture was poured into a large amountof water, and then extracted with hexane. The combined organic layers were washedwith water, and dried over anhydrous MgSO4. After filtration and evaporation, theproduct was purified by silica gel column chromatography (eluent: hexane), and driedunder vacuum to give 6 as a yellow oil (yield = 6.60 g, 58%). 1H NMR (500 MHz,CDCl3): 7.87 (d, J = 1.5 Hz, 1H), 7.77 (d, J = 8.5 Hz, 1H), 7.44 (d, J = 5.5 Hz, 1H),7.36 (dd, J = 8.0, 1.5 Hz, 1H), 7.28 (d, J = 5.0 Hz, 1H), 2.43 (t, J = 7.0 Hz, 2 H),1.66-1.53 (m, 2H) , 1.51-1.44 (m, 2H), 1.37-1.31 (m, 4H), 0.91 (t, J = 7.0 Hz, 3H).13C{1H} NMR (125 MHz, CDCl3): 139.64, 138.96, 127.59, 127.12, 126.79, 123.66,122.29, 120.20, 90.02, 80.89, 31.52, 28.93, 28.77, 22.71, 19.60, 14.19.

The synthetic route of 4923-87-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Mieno, Hiroyuki; Yasuda, Takuma; Yang, Yu Seok; Adachi, Chihaya; Chemistry Letters; vol. 43; 3; (2014); p. 293 – 295;,
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Benzothiophene | C8H6S – PubChem

360575-29-7, Methyl 4-bromobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of methyl 4-bromobenzo[b]thiophene-2-carboxylate (101 g), sodium hydroxide (63 g), methanol (1200 ml) and water (600 ml) was stirred at ambient temperature for 16 hours, the methanol was removed in vacuo, and the resulting suspension was cooled to 0 C. and acidified by dropwise addition of concentrated hydrochloric acid. The mixture was stirred for 20 minutes and the resulting solid was collected by filtration, washed with water (3*250 ml) and dried in vacuo at 110-120 C. to give 4-bromobenzo[b]thiophene-2-carboxylic acid (62 g) as a cream solid which was used without further purification., 360575-29-7

The synthetic route of 360575-29-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Doyle, Kevin James; Kerrigan, Frank; Watts, John Paul; US2003/166628; (2003); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

1423-61-6, 7-Bromobenzo[b]thiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a stirring solution of diisopropylamine (2.374 g, 23.46 mmol) in THF (12 mL) at -70 C under nitrogen was added butyllithium (8.26 mL, 20.65 mmol, 2.5M solution in hexanes). After 15 minutes at -70 C was added 7- bromo-l-benzothiophene (4.0 g, 18.77 mmol, Intermediate X13) in THF (10 mL). The cooling bath was removed and reaction warmed to -30 C then returned to -70 C. To the colorless solution was added di-tert-butyl (6-((E)- (((S)-tert-butylsulfinyl)imino)methyl)-5-chloro-2-pyridinyl)imidodicarbonate (8.63 g, 18.77 mmol, Intermediate AA4) in THF (15 mL) at a rate not to exceed – 60 C. After 18 h of warming to 20 C, the reaction was quenched with sat. NH4C1 (20 mL). The reaction was then partitioned between EtOAc (120 mL) and sat NH4C1 (50 mL). The organic was the dried over MgS04, concentrated onto dry silica (30 g) under reduced pressure, then purified by silica gel chromatography (330 g) eluting products with 10 to 50% EtOAc in hexanes to afford tert-butyl (6-((7-bromo-l-benzothiophen-2-yl)(((S)-tert- butylsulfinyl)amino)methyl)-5-chloro-2-pyridinyl)carbamate (6.0 g) as a white solid., 1423-61-6

The synthetic route of 1423-61-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AMGEN INC.; ASHTON, Kate; BARTBERGER, Michael D.; BOURBEAU, Matthew Paul; CROGHAN, Michael D.; FOTSCH, Christopher H.; HUNGATE, Randall W.; KONG, Ke; NISHIMURA, Nobuko; NORMAN, Mark H.; PENNINGTON, Lewis D.; REICHELT, Andreas; SIEGMUND, Aaron C.; TADESSE, Seifu; ST. JEAN, David Jr; YANG, Kevin C.; YAO, Guomin; WO2013/173382; (2013); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

360576-01-8, Methyl 6-bromobenzo[b]thiophene-2-carboxylate is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

LiOH.H20 (1.85g, 44mmol) and water (20mL) were added to a stirred solution of 6-bromo-benzo[b]thiophene-2-carboxylic acid methyl ester (I-25a: 2.4g, 8.85mmol) in THF (25mL) at room temperature. The resulting mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC (100% ethyl acetate). The reaction mixture was concentrated, acidified with 2N HCl, filtered and the residue was washed with n-hexane to afford 1.9g of the product (84% yield).1H NMR (DMSO-D6, 300 MHZ): 814.0-14.03 (b, 1H), 8.4-8.39 (d, 1H), 8.28- 8.1 (d, 1H), 8.18-8.0 (d, 1H), 7.78-7.62 (dd, 1H). LCMS Purity: 99%, m/z = 255.9 (M+l)

360576-01-8, 360576-01-8 Methyl 6-bromobenzo[b]thiophene-2-carboxylate 22474078, abenzothiophene compound, is more and more widely used in various fields.

Reference£º
Patent; NOVARTIS AG; BOCK, Mark Gary; GAUL, Christoph; GUMMADI, Venkateshwar Rao; SENGUPTA, Saumitra; WO2012/149413; (2012); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem