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
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