With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.104795-85-9,Methyl 6-chlorobenzo[b]thiophene-2-carboxylate,as a common compound, the synthetic route is as follows.
To a solution of 600 mg (3.23 mmol) of 4-chloro-2-nitro-benzaldehyde in DMF (7 ml) were added 559 mg (4.04 mmol) of potassium carbonate and 294 mul (3.23 mmol) of methyl thioglycolate at 0 C. The reaction mixture was stirred for 30 min at 0 C. and then for 24 h at RT. Then the mixture was poured into ice-water and the precipitate was collected by filtration and dissolved in ethyl acetate. The solution was dried (MgSO4) and concentrated to yield 630 mg (86%) of 6-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester as a white solid. 1HNMR (CDCl3, 300 MHz): delta 3.95 (s, 3H), 7.88 (dd, J=8.6 and 1.9 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H), 7.85 (d, J=1.9 Hz, 1H), 8.02 (s, 1H).To a solution of 630 mg (2.78 mmol) of 6-chloro-benzo[b]thiophene-2-carboxylic acid methyl ester in THF (5 ml) were added 6.95 ml of 1N LiOH-solution and the reaction mixture was stirred at RT for 4 h. The pH was then adjusted to 2-3 by addition of 1N HCl and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to yield 579 mg (98%) of 6-chloro-benzo[b]thiophene-2-carboxylic acid as white solid. MS (ISP) 211.0 (M-H)-.In analogy to example S3 (steps a to b) 139 mg (0.65 mmol) of 6-chloro-benzo[b]thiophen-2-carboxylic acid were converted into 52 mg (0.14 mmol) of (6-chloro-benzo[b]thiophen-2-ylmethyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine. The product was obtained as colorless liquid. MS (ISP) 370.0 (M+H)+.
104795-85-9, 104795-85-9 Methyl 6-chlorobenzo[b]thiophene-2-carboxylate 18526200, abenzothiophene compound, is more and more widely used in various fields.
Reference£º
Patent; Faeh, Christoph; Kuehne, Holger; Luebbers, Thomas; Mattei, Patrizio; Maugeais, Cyrille; Pflieger, Philippe; US2007/185113; (2007); A1;,
Benzothiophene – Wikipedia
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