With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10133-22-9,5-(Bromomethyl)benzo[b]thiophene,as a common compound, the synthetic route is as follows.
Add potassium carbonate (0.619 g, 4.4 mmol, 1.6 eq) followed by 5-bromomethyl- benzo [b] thiophene (17.7 g, 78 mmol, 1 eq) in one portion to a stirred solution of 1,1- dimethylethyl 4- [ (2-methylpropyl) amino] piperidine-1-carboxylate (20 g, 78 mmol, 1 eq) in acetonitrile (400 ml). Cool, add water (250 ml) then filter. Wash the solid with ice cold acetonitrile and leave to dry on sinter for 1 hr. Purify on a 330 g Redisep column (20 g per column) using a gradient of 0-40% Ethyl acetate/iso-hexane to give 1,1- dimethylethyl 4- { [ (l-benzothienyl-5-yl] methyl]- (2-methylpropyl) amino}-piperidine-1- carboxylate (7.64 g, 46 %) as yellow solid. LCMS Rt= 3.38 (6 min gradient) M++1 : 403.5. 1H NMR (300 MHz, CDC13) 6 ppm 7.80-7. 60 (2 H, m), 7.37-7. 33 (1 H, m), 7.32- 7.26 (1 H, m), 7.25-7. 20 (1 H, m), 4.17-3. 94 (2 H, m), 3.65 (2 H, s), 2.65-2. 36 (3 H, m), 2.24-2. 10 (2 H, d), 1.71-1. 28 (5 H, m), 1.38 (9 H, s), 0.88-0. 69 (6 H, d).
10133-22-9, As the paragraph descriping shows that 10133-22-9 is playing an increasingly important role.
Reference£º
Patent; ELI LILLY AND COMPANY; WO2005/92885; (2005); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem