Category: 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,5381-20-4

A mixture of thianaphthene-3-carboxaldehyde (0.2 g, 1.23 mmol), acetylacetone (0.25 mL, 2.47 mmol) and aqueous ammonium hydroxide solution (38-40%, 0.12 mL) in ethanol (1 mL) was heated to 90C and left to stir for 16 hours. The mixture was allowed to cool to RT and was then poured into 10 ml of cold water. The precipitate formed was filtered off, dried and washed with cold diethyl ether. The desired product was obtained as a strongly yellow solid (0.193 g, 48 %). 1H-NMR (400 MHz, DMSO-d6) delta = 2.17 (s, 6H), 2.29 (s, 6H), 5.52 (s, 1H), 7.23 (s, 1H), 7.33 (dt 2H), 7.88 (d, 1H), 8.12 (d, 1H), 9.08 (s, 1H). HPLC-MS: Rt 3.668 min, m/z 192.1 (MH+-134). The following examples were synthesized according to Method G.

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

Reference£º
Patent; Oncostellae, S.L.; KURZ, Guido; CAMACHO GOMEZ, Juan; (123 pag.)EP3480201; (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, General procedure: Amixture of the heterocyclic salt I1-I16 (2.5 mmol), aldehyde (7.5 mmol, 3 molar equiv, unlessotherwise stated) and piperidine (0.50 mL, 5 mmol, 2 molar equiv) in EtOH (25 mL) was heatedunder reflux for 2.5 h. After cooling to room temperature, the precipitated solid was collectedby filtration, washed with EtOH (2 ¡Á 5 mL) and Et2O (2 ¡Á 5 mL) and dried. The crude iodidesalt was either purified through a recrystallization from a suitable solvent (as indicated below)to give an analytically pure sample, or subjected to anion exchange to bromide or chloride, asdescribed below. Procedure for anion exchange: Ion-exchange resin (Amberlite IRA-402, Cl- form, or AmberliteIRA-400, Br- form, about 20 mmol equiv) was thoroughly rinsed with a mixture of MeCN andMeOH (1:1, v/v) and charged into a short glass column. The dye (iodide salt) was dissolvedin a minimal amount of a mixture of MeCN and MeOH (1:1, v/v) and loaded in the column. Theproduct was then eluted with the same solvent mixture (about 50 mL). The solvents wereremoved in vacuo and the residue was recrystallized from a suitable solvent (as indicatedbelow), to give an analytically pure dye.

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

Reference£º
Article; Xie, Xiao; Zuffo, Michela; Teulade-Fichou, Marie-Paule; Granzhan, Anton; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1872 – 1889;,
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 2-(3-(trifluoromethyl)phenyl)benzo[b]thiophene-3-carbaldehyde (29a): Benzo[b]thiophene-3-carbaldehyde (27) (162 mg, 1.0 mmol) in THF (2 mL) was added to a solution of TMPZnCl.LiCl (2) (1.3 M in THF, 0.85 mL, 1.1 mmol) at 25 C. and the reaction mixture was then stirred at this temperature for 30 min according to TP 2. Pd(dba)2 (17 mg, 3 mol %) and P(o-furyl)3 (14 mg, 6 mol %) dissolved in THF (2 mL), and mixed with 3-iodobenzomethyltrifluoride (354 mg, 1.3 mmol, 1.3 equiv) were then transferred via cannula to the reaction mixture. The resulting mixture was stirred for 1 h at 25 C. The reaction mixture was then quenched with a sat. aq. NH4Cl solution (20 mL), extracted with diethyl ether (3¡Á50 mL) and driedanhydrous Na2SO4. After filtration, the solvent was evaporated in vacuo. Purification by flash-chromatography (CH2Cl2/n-pentane, 1:3) furnished compound 29a (281 mg, 92%) as a colourless solid. m.p.: 102.8 – 104.2 C.1H-NMR (400 MHz, CDCl3) delta: 10.02 (s, 1 H), 8.79 (m, 1 H), 7.45-7.87 (m, 7 H).13C-NMR (100 MHz, CDCl3) delta: 185.9, 158.0, 138.0, 136.8, 133.7, 132.4, 131.5 (q, J (C-F)=33.0 Hz), 130.7, 129.5, 127.0 (q, J (C-F)=3.8 Hz), 126.6 (q, J (C-F)=3.8 Hz), 126.5, 126.2, 123.5 (q, J (C-F)=272.5 Hz), 121.7.MS (70 eV, El) m/z (%): 306 (97) [M+], 305 (100), 278 (12), 257 (13), 237 (28), 233 (18), 208 (29), 160 (13), 44 (40).IR (ATR) v (cm-1): 3068, 2866, 2359, 1926, 1745, 1669, 1590, 1520, 1483, 1459, 1438, 1421, 1392, 1351, 1325, 1310, 1288, 1265, 1217, 1178, 1156, 1118, 1097, 1092, 1073, 1051, 1018, 1000, 994, 966, 947, 933, 907, 868, 863, 812, 773, 754, 733, 703, 679, 653, 641, 633, 620, 608, 603.HRMS (El) for C16H9F3OS (306.0326): 306.0326.

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

Reference£º
Patent; Knochel, Paul; Mosrin, Marc; US2011/288296; (2011); 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, 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.

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

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

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, 1-Benzothiophene-3-carbaldehyde (6.17 mmole), 1-(2-pyridinyl)piperazine (6.17 mmole), and sodium triacetoxyborohydride (9.26 mmole) were combined in 25 mL of 1,2-dichloroethane and stirred at 0 C. for one hour. The mixture was allowed to warm to room temperature and stir for 12 hours. The mixture was poured into a diethyl ether:dichloromethane mixture and washed with a solution of saturated aqueous NaCl made basic with sodium hydroxide solution. The organic phase was dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography with 96:4:0.5 dichloromethane/methanol/saturated aqueous ammonia to provide the title compound. 1H NMR (d6-DMSO, 300 MHz) delta 2.62 (t, 4H, J=4.5 Hz), 3.51 (t, 4H, J=4.5 Hz), 3.82 (s, 2H), 6.65 (m, 1H), 6.80 (d, 1H, J=8.7 Hz), 7.40 (m, 2H), 7.48 (s, 1H), 7.53 (m, 1H), 7.86 (m, 1H), 8.04 (m, 2H); MS (DCI/NH3) m/z 310.0 (M+H)+.

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

Reference£º
Patent; Cowart, Marlon D.; Latshaw, Steven P.; Nelson, Sherry L.; Stewart, Andrew O.; US2006/172995; (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.5381-20-4,Thianaphthene-3-carboxaldehyde,as a common compound, the synthetic route is as follows.

5381-20-4, To a solution of l-benzothiophene-5-carbaldehyde (800 mg, 5 mmol) in MeOH (10 mL) was added sodium tetrahydroborate (0.28 g, 7.4 mmol) at 0 C. The reaction mixture was allowed to stir at 0 C for lh, at which point a saturated aqueous solution of H4C1 (50 mL) and water (50 mL) was added. The mixture was extracted with DCM (3x). The organic solutions were combined, dried over MgS04, filtered, and concentrated to dryness. The crude solid was then dissolved in DCM (100 mL) under argon and triphenyl phosphine (2.30 g, 8.78 mmol) and carbon tetrabromide (2.0 g, 5.9 mmol) were added. After stirring for lh, diethyl ether was added and the resulting mixture was filtered and washed with diethyl ether (2x). The filtrate was concentrated to dryness and the crude residue was purified by column chromatography to afford 5-(bromomethyl)-l-benzothiophene (760 mg, 70 %) as a white solid. 1H MR (400 MHz, CDCI3) delta 7.80 – 7.92 (m, 2H), 7.51 (d, J=5.4 Hz, 1H), 7.41 (dd, J=8.3, 1.8 Hz, 1H), 7.35 (d, J=5.4 Hz, 1H), 4.68 (s, 2H).

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

Reference£º
Patent; MILLENNIUM PHARMACEUTICALS, INC.; ADHIKARI, Sharmila; CALDERWOOD, Emily, Frances; ENGLAND, Dylan, Bradley; GOULD, Alexandra, E.; HARRISON, Sean, J.; HUANG, Shih-Chung; MA, Liting; (316 pag.)WO2018/89786; (2018); 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.

Example 7: Synthesis o -(benzothiophen-3-yl)-2-hydroxyethylsulfamide[00109] 2-Amino-l-benzo[b]thiophen-3-yl-ethanol hydrochloride salt. To a stirring solution of thiophene-3-carbaldehyde (3.0 g, 17.94 mmol) and trimethylsilyl cyanide (2.68 mL, 19.73 mmol) in dichloromethane (20 mL) at room temperature under nitrogen was added a few crystals of zinc iodide. The mixture was stirred at this temperature for 20 hours and concentrated. The residue was dissolved in borane in tetrahydrofuran (1M, 40 mL) and heated to reflux for 5 hours. The mixture was cooled to room temperature and concentrated. The syrup was dissolved in methanol (60 mL), treated with hydrogen chloride (4M in dioxane, 20 mL), and heated to reflux for 2 hours, and then concentrated. The solid obtained was dissolved in aqueous hydrochloric acid (2N, 10 mL) and extracted twice with diethyl ether. The aqueous solution was concentrated, crystallized from methanol/ethyl acetate, and dried in vacuum oven to give a yellow solid (2.4 g, 58%)., 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; ADVANCED NEURAL DYNAMICS, INC.; FOX CHASE CHEMICAL DIVERSITY CENTER, INC.; SMITH, Garry, Robert; BRENNEMAN, Douglas, Eric; REITZ, Allen, B.; DU, Yanming; WO2011/97337; (2011); 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, [1-BENZOTHIOPHENE-3-CARBALDEHYDE] (6.17 mmole), 1-(2-pyridinyl) piperazine (6.17 mmole), and sodium triacetoxyborohydride (9.26 mmole) were combined in 25 mL of 1,2- dichloroethane and stirred at 0C for one hour. The mixture was allowed to warm to room temperature and stir for 12 hours. The mixture was poured into a diethyl ether : dichloromethane mixture and washed with a solution of saturated aqueous NaCl made basic with sodium hydroxide solution. The organic phase was dried over sodium sulfate, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography with 96: 4: 0.5 dichloromethane/methanol/saturated aqueous ammonia to provide the title [COMPOUND. IH] NMR (d6-DMSO, 300 MHz) 8 2.62 (t, 4H, J=4. [5HZ),] 3.51 (t, 4H, [J=4.] [5HZ),] 3.82 (s, 2H), 6.65 (m, 1H), 6.80 (d, [1H,] J=8.7Hz), 7.40 [(M,] 2H), 7.48 (s, [1H),] 7.53 [(M,] 1H), 7.86 [(M,] 1H), 8. 04 [(M,] 2H); MS (DCI/NH3) m/z 310.0 (M+H) +.

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

Reference£º
Patent; Abbott Laboratories; WO2003/101994; (2003); 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

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¡Á75 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

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

Reference£º
Patent; Smith-Swintosky, Virginia L.; US2007/191449; (2007); A1;; ; Patent; Smith-Swintosky, Virginia L.; US2007/191452; (2007); 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, A suspension of [1-BENZOTHIOPHENE-3-CARBALDEHYDE] (4.9 g, 0.03 mol), malonic acid (6.6 g, 0.06 mol) and piperidine (1 mL) in 100 mL anhydrous pyridine was heated at [110C] overnight. The reaction mixture was cooled to room temperature and the solvent was removed in vacuo. The residue was taken up in 100 [ML] of water and 1 N hydrochloric acid was added to adjust the pH of this solution to ca. 3. The suspension was filtered and the yellow solid was collected, washed with water (3 x 50 [RNL)] and concentrated in vacuo to give the indicated product with 95% purity (5.65g, 91%).

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

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2003/104236; (2003); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem