Category: 5381-20-4

5381-20-4,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.

A mixture of thianaphthene-3-carboxaldehyde (0.5 g, 3.08 mmol), 3-aminocrotonitrile (0.554 mL, 6.74 mmol) and acetic acid (0.076 mL, 3.08 mmol) in isopropyl alcohol (10 mL) was stirred at 100C for 18 hours. The mixture was allowed to cool to RT and concentrated. The residue was basified with aq. sodium bicarbonate, and the resulting solid was filtered off and washed with cold water and ethyl ether. The desired product was obtained as a light-yellow solid (0.738 g, 82 %). 1H-NMR (400 MHz, DMSO-d6) delta = 2.06 (s, 6H), 5.00 (s, 1H), 7.36-7.46 (m, 1H), 7.65 (s, 1H), 7.89 (d, 1H), 8.03 (d, 1H), 9.67 (s, 1H). HPLC-MS: Rt 3.878 min, m/z 292.0 (MH+).

The synthetic route of 5381-20-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Oncostellae, S.L.; KURZ, Guido; CAMACHO GOMEZ, Juan; (123 pag.)EP3480201; (2019); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4,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.

[0626j To a solution of benzo[b]thiophene-3-carboxaldehyde (8-A) (3.22 g, 20 mmol) in THF (20 mL), vinyl magnesium bromide (20 mmol, 1M in Et20) was added dropwise at rt. The mixture was stirred for 2 h at rt. The mixture was treated with aqueous NH4C1 and extracted with EA. The organic phase was concentrated and the residue was purified by column chromatography on silica gel (PE:EA = 50:1) to afford 9-D (2.50 g, 65.7

5381-20-4 Thianaphthene-3-carboxaldehyde 227328, abenzothiophene compound, is more and more widely used in various.

Reference£º
Patent; ALIOS BIOPHARMA, INC.; WANG, Guangyi; BEIGELMAN, Leonid; TRUONG, Anh; NAPOLITANO, Carmela; ANDREOTTI, Daniele; HE, Haiying; WO2014/31784; (2014); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4,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.

Example 3; N2-{-3-[(1-benzothien-3-ylmethyl)amino]-trans-cyclohexyl}-N4,N4- dimethylquinazoline-2, 4-diamine; A solution of N2- (3-amino-t7-ans-cyclohexyl)-N4, N4-dimethyl-quinazoline-2, 4-diamine (0.237 g, 0. 83 mmol, from Example 2b) and benzo [b] thiophene-3-carbaldehyde (0.135 g, 0.83 mmol) in MeOH : DCM (1: 2, containing 1% HOAc, 20 mL) was stirred at ambient temperature for 1.5 h, after which a solution of NaBH3CN (0.104 g, 1.66 mmol) in MeOH (4 mL) was added. The reaction mixture was stirred at room temperature until TLC indicated that starting material was consumed. Methanol (20 mL) was added and the reaction mixture was concentrated. The residue was purified on Si02 eluted with DCM: MeOH (98 : 2) containing 2% Et3N and finally DCM: MeOH (9: 1) containing 2% Et3N to give 0. 310 g (86%) of the title compound. This material was dissolved in MeCN and further purified by HPLC (Eluent A: H20 containing 0. 1% TFA; Eluent B: MeCN ; gradient from 10% to 80% of eluent B) to give 0.200 g (56%) of the title compound. 1HNMR (300.1 MHz, MeOD-d4) 8 7.82 (d, 1H), 7.76 (m, 1H), 7.45 (t, 1H), 7.05-7. 33 (m, 5H), 7.01 (t, 1H), 4.32 (br s, 1H), 3.96 (s, 2H), 3.18 (s, 6H), 2.90 (m, 1H), 1.3-2. 1 (m, 8H). 13CNMR (75.5 MHz, MeOD-d4) 8 164.7, 158. 0,153, 3,140. 7, 138. 5,134. 6,132. 3,128. 7, 128.0, 126.6, 124.2, 123.9, 123.3, 122.5, 121.4, 120. 0, 111.8, 51.9, 46.0, 43.8, 40.9, 36.6, 31.3, 31.2, 19.8. LC-MS [M+H] +432. 2.

The synthetic route of 5381-20-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ASTRAZENECA AB; WO2005/70902; (2005); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4,5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a dry glass reaction tube purged with argon and equipped with a magnetic stir bar were added molecular sieves (3-4 A, 100 mg), aldehyde 3a (46 mg, 0.25 mmol), Pd-gamma-Fe2O3 (24 mg, 5 mol% Pd), and cyclohexane (1 mL) and the sealed tube was heated at 130 C for 24 h. The reaction mixture was decanted with the help of an external magnet and the catalyst was washed with CH2Cl2 (5 x 5 mL). The crude product was purified by dry-flash chromatography (SiO2: hexane) to afford 4a (31 mg, 82%) as a white solid; mp 66-68 C.

5381-20-4 Thianaphthene-3-carboxaldehyde 227328, abenzothiophene compound, is more and more widely used in various.

Reference£º
Article; Ajda?i?, Vladimir; Nikoli?, Andrea; Simi?, Stefan; Manojlovi?, Dragan; Stojanovi?, Zoran; Nikodinovic-Runic, Jasmina; Opsenica, Igor M.; Synthesis; vol. 50; 1; (2018); p. 119 – 126;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,5381-20-4

General procedure: Benzo[b]thiophene-3-carbaldehyde (40 mg, 0.25 mmol, 1.0 equiv),Pd(TFA) 2 (4.2 mg, 5 mol%), (4-FC 6 H 4 ) 3 P (9.5 mg, 12 mol%), DPEphos (8mg, 6 mol%), and Cs 2 CO 3 (122 mg, 0.375 mmol) were placed in atransparent Schlenk tube equipped with a stirring bar. The tube wasevacuated and filled with argon for three times. Degassed DMF (2.5mL) and tert-butyl bromide (51 mg, 0.375 mmol, 1.5 equiv) were add-ed via a gastight syringe. The reaction mixture was stirred under theirradiation of 36 W blue LEDs (distance app. 2.0-3.0 cm from thebulb) at r.t. for 24 h. The mixture was quenched with brine and ex-tracted with EtOAc (3 ¡Á 10 mL). The organic layers were combinedand concentrated under reduced pressure. The product was purifiedby flash column chromatography on silica gel using PE or a mixture of PEand EtOAc (10:1 v/v) as eluent; yield: 50.1 mg (92%); pale yellow liquid.

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

Reference£º
Article; Wang, Guang-Zu; Shang, Rui; Fu, Yao; Synthesis; vol. 50; 15; (2018); p. 2908 – 2914;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5381-20-4, General procedure: An aqueous solution of NaOH (3M, 1.6mL) was added to a solution of aromatic ketone (1mmol) and 3-methoxybenzaldehyde (1.2 eq), in EtOH (1-2mL). The reaction was stirred at r.t for 18-24h. The reaction mixture was cooled in an ice-water bath and acidified to pH 2 with concentrated HCl (37%). The solid formed was filtered, washed with ethanol and then further purified by recrystallization from ethanol. When no precipitate occurred, the reaction mixture was extracted with dichloromethane and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. Column chromatography was then utilized to purify the desired product.

The synthetic route of 5381-20-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Borsari, Chiara; Jimenez-Anton, Maria Dolores; Eick, Julia; Bifeld, Eugenia; Torrado, Juan Jose; Olias-Molero, Ana Isabel; Corral, Maria Jesus; Santarem, Nuno; Baptista, Catarina; Severi, Leda; Gul, Sheraz; Wolf, Markus; Kuzikov, Maria; Ellinger, Bernhard; Reinshagen, Jeanette; Witt, Gesa; Linciano, Pasquale; Tait, Annalisa; Costantino, Luca; Luciani, Rosaria; Tejera Nevado, Paloma; Zander-Dinse, Dorothea; Franco, Caio H.; Ferrari, Stefania; Moraes, Carolina B.; Cordeiro-da-Silva, Anabela; Ponterini, Glauco; Clos, Joachim; Alunda, Jose Maria; Costi, Maria Paola; European Journal of Medicinal Chemistry; vol. 183; (2019);,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Benzo[b]thiophene-3-carbaldehyde (40 mg, 0.25 mmol, 1.0 equiv),Pd(TFA) 2 (4.2 mg, 5 mol%), (4-FC 6 H 4 ) 3 P (9.5 mg, 12 mol%), DPEphos (8mg, 6 mol%), and Cs 2 CO 3 (122 mg, 0.375 mmol) were placed in atransparent Schlenk tube equipped with a stirring bar. The tube wasevacuated and filled with argon for three times. Degassed DMF (2.5mL) and tert-butyl bromide (51 mg, 0.375 mmol, 1.5 equiv) were add-ed via a gastight syringe. The reaction mixture was stirred under theirradiation of 36 W blue LEDs (distance app. 2.0-3.0 cm from thebulb) at r.t. for 24 h. The mixture was quenched with brine and ex-tracted with EtOAc (3 ¡Á 10 mL). The organic layers were combinedand concentrated under reduced pressure. The product was purifiedby flash column chromatography on silica gel using PE or a mixture of PEand EtOAc (10:1 v/v) as eluent; yield: 50.1 mg (92%); pale yellow liquid.1 H NMR (400 MHz, CDCl 3 ): delta = 10.75 (s, 1 H), 8.68 (d, J = 8.1 Hz, 1 H),7.76 (d, J = 8.0 Hz, 1 H), 7.47-7.43 (m, 1 H), 7.38-7.34 (m, 1 H), 1.66 (s,9 H).13 C NMR (101 MHz, CDCl 3 ): delta = 185.9, 172.5, 138.7, 135.6, 129.4,125.9, 125.0, 124.8, 121.3, 36.6, 33.3.HRMS (ESI): m/z calcd for C 13 H 15 OS + [M + H] + : 219.0838; found:219.0839., 5381-20-4

The synthetic route of 5381-20-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Wang, Guang-Zu; Shang, Rui; Fu, Yao; Synthesis; vol. 50; 15; (2018); p. 2908 – 2914;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A mixture of thianaphthene-3-carboxaldehyde (0.106 g, 0.65 mmol), methyl 3-cyclopropyl-3-oxopropanoate (0.071 g, 0.72 mmol) and 4-amino-3-penten-2-one (0.088 g, 0.61 mmol) and acetic acid (0.035 mL) in isopropylalcohol (1.5 mL) was heated to 100C and left to stir for 19 hours. The mixture was allowed to cool to RT and was then treated with saturated aqueous sodium bicarbonate solution (10 mL). The solid was filtered off, washed with water, dried and purified by column chromatography (4:1 hexane: ethyl acetate) affording a fine yellow solid (0.075 g, 44 %). 1H-NMR (400 MHz, DMSO-d6) delta = 0.76 (s, 2H), 0.96 (d, 2H), 2.12 (s, 3H), 2.33 (s, 3H), 2.69 (s, 1H), 3.58 (s, 3H), 5.43 (s, 1H), 7.15 (s, 1H), 7.31 (s, 1H), 7.38 (s, 1H), 7.90 (s, 2H), 8.05 (d, 1H). HPLC-MS: Rt 4.302 min, m/z 234.1 (MH+-133). (0600) A second reaction product was isolated by column chromatography: Example J1-a: Dimethyl 4-(benzo[b]thiophen-3-yl)-2,6-dicyclopropyl-1,4-dihydropyridine-3,5-dicarboxylate (0601) 1H-NMR (400 MHz, DMSO-d6) delta = 0.56 (s, 2H), 0.82 (s, 2H), 0.90 (d, 2H), 1.04 (s, 2H), 2.56 (m, 2H), 3.55 (s, 5H), 5.37 (s, 1 H), 7.05 (s, 1 H), 7.11 (s 1 H), 7.32 (t, 1 H), 7.39 (t, 1H), 7.90 (d, 1 H), 7.98 (s, 1 H). HPLC-MS: Rt 4.935; m/z 276.1 (MH+)., 5381-20-4

The synthetic route of 5381-20-4 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Oncostellae, S.L.; KURZ, Guido; CAMACHO GOMEZ, Juan; (123 pag.)EP3480201; (2019); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

5381-20-4, General procedure: Titanium tetrachloride (1.90 g, 10 mmol) was slowly added to100 mL of anhydrous THF at 0 C, followed by addition of 5 mmol of the aldehyde (1) and stirred for 10 min, then ethyl 2-(3-bromopyridin-2-yl)acetate (2) (1.47 g, 6 mmol) was added. Subsequently, a solution of pyridine (3.16 g, 40 mmol) in 25 mL of anhydrous THF was added dropwise during a period of 30-60 min at 0 C. The reaction mixture was then stirred for 1 h at room temperature and refluxed for 24 h. After that the mixture was poured on to crashed ice and extracted with ethyl acetate (4 30 mL). The combined extracts were successively washed with brine, saturated sodium hydrogen carbonate and brine, and then dried over anhydrous MgSO4. The organic phase was filtrated and the solvent was removed in vacuo, the residue was purified by column chromatography (silica gel) using PE/EA (5:1) / DCM/MeOH (50:1) to provide 3.

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

Reference£º
Article; Li, Bo; Yue, Zhi-Zhou; Feng, Jian-Ming; He, Qian; Miao, Ze-Hong; Yang, Chun-Hao; European Journal of Medicinal Chemistry; vol. 66; (2013); p. 531 – 539;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

5381-20-4,5381-20-4, Thianaphthene-3-carboxaldehyde is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a 20-mL sealed tube purged and maintained with an inert atmosphere of nitrogen,was placed a solution of 2-ethyl-5-[(3-methylcyclohexyl)oxyjaniline (1.0 g,4.29 mmol,as prepared in the previous step) in EtOH (10 mL) then 2-oxopropanoic acid (1.13 g,12.83 mmol) and 1-benzothiophene-3-carbaldehyde (626 mg,3.86 mmol) were added. The reaction was stirred overnight at 120C then concentrated under reduced pressure. The crude product was purified by Flash-PrepHPLC (IntelFlash-1: Column,C18; mobile phase,ACN,water (0.5% TFA) and ACN (80.0%ACN up to 95.0% in 15 mm); Detector,UV 254 nm) then the isomers were separated by PrepSFC (Prep 5FC350-2: Column,CHIRALPAK AD-H SFC,5*25cm,Sum; mobile phase,C02(50%),ethanol(2mM NH3-MeOH); Detector,UV 254 nm) affording 56.7 mg (3%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 R,3 S)-3-methylcyclohexylj oxyl quinoline-4-carboxylic acid (Compound 182) as alight yellow solid,53.9 mg(4%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 R,3R)-3-methylcyclohexyll oxyl quinoline-4-carboxylic acid (Compound 184) as a light yellow solid and a mixture of Compound 181 and Compound 183. This mixture was separated by Chiral-Prep-HPLC (HPLC-09: Column: CHIRALPAK-AD-H-5L002,20*250 mm; Mobile Phase A:Hex–HPLC,Mobile Phase B: IPA–HPLC; Flow rate: 15 mL/min; Gradient: 40 B to 40 B in 16 mm; 254 nm) affording 55.7 mg (3%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 S,3R)-3-methylcyclohexyll oxyl quinoline-4-carboxylic acid (Compound 181) as a brown solid and 56.8 mg (3%) of 2-(1-benzothiophen-3-yl)-8-ethyl-5-[[(1 S,35)-3-methylcyclohexyljoxyjquinoline-4-carboxylic acid (Compound 183) as a brown solid. j0401j 2-(1-Benzothiophen-3-yl)-8-ethyl-5-j j(1S,3R)-3-methylcyclohexyljoxyjquinoline-4-carboxylic acid (Compound 181): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (brs,1H ),9.26 (d,J= 7.5 Hz,1H ),8.81 (s,1H ),8.12 (d,J= 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.02 (d,J= 8.1H z,1H ),4.86-4.85 (m,1H ),3.25 (q,J= 7.5Hz,2H),1.97-1.72 (m,4H),1.70-1.61 (m,1H ),1.60-1.45 (m,2H),1.37 (t,J= 7.5 Hz,3H),1.10-0.93 (m,1H ),0.87 (d,J= 6.3 Hz,1H ). HPLC purity (254 nm): 99.5%.j0402j 2-(Benzo jbjthiophen-3-yl)-8-ethyl-5-(((1R,3S)-3-methylcyclohexyl)oxy)quinoline-4-carboxylic acid (Compound 182): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (brs,1H ),9.26 (d,J= 7.5 Hz,1H ),8.81 (s,1H ),8.12 (d,J= 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.02 (d,J= 8.1H z,1H ),4.86-4.85 (m,1H ),3.25 (q,J= 7.5Hz,2H),1.97-1.72 (m,4H),1.70-1.61 (m,1H ),1.60-1.45 (m,2H),1.37 (t,J 7.5 Hz,3H),1.10-0.93 (m,1H ),0.87 (d,J= 6.3 Hz,1H ). HPLC purity (254 nm): 99.7%.j0403j 2-(Benzo jbjthiophen-3-yl)-8-ethyl-5-(((1S,3S)-3-methylcyclohexyl)oxy)quinoline-4-carboxylic acid (Compound 183): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (s,1H ),9.27 (d,J= 7.8 Hz,1H ),8.81 (s,1H ),8.12 (d,J 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.11 (d,J= 8.1H z,1H ),4.50-4.57 (m,1H ),3.24 (q,J= 7.5Hz,2H),2.10-2.13 (m,2H),1.47-1.80 (m,3H),1.29-1.43 (m,5H),1.10-1.28 (m,1H ),0.94 (d,J= 6.6 Hz,3H),0.79-0.89 (m,1H ). HPLC purity (254 nm): 99.6%.j0404j 2-(Benzo jbjthiophen-3-yl)-8-ethyl-5-(((1R,3R)-3-methylcyclohexyl)oxy)quinoline-4-carboxylic acid (Compound 184): Mass Spectrum(LCMS,ESI pos): Calcd. for C27H28NO3S: 446.2 (M+H); Found: 446.2. 1H NMR (300 MHz,DMSO-d6): oe 13.14 (s,1H ),9.27 (d,J= 7.8 Hz,1H ),8.81 (s,1H ),8.12 (d,J 7.8 Hz,1H ),8.04 (s,1H ),7.46-7.61 (m,3H),7.11 (d,J= 8.1H z,1H ),4.50-4.57 (m,1H ),3.24 (q,J= 7.5Hz,2H),2.10-2.13 (m,2H),1.47-1.80 (m,3H),1.29-1.43 (m,5H),1.10-1.28 (m,1H ),0.94 (d,J= 6.6 Hz,3H),0.79-0.89 (m,1H ). HPLC purity (254 nm): 99.7%.

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

Reference£º
Patent; PROTEOSTASIS THERAPEUTICS, INC.; MUNOZ, Benito; BASTOS, Cecilia, M.; PARKS, Daniel; KOMBO, David; (301 pag.)WO2017/62581; (2017); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem