5381-20-4 Thianaphthene-3-carboxaldehyde 227328, abenzothiophene compound, is more and more widely used in various.
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 stirred solution of JV-Boc-2-AH (0.11 mmol) in ethanol (5 mL) was added30 triethylamine (0.16 mmol) and 3-benzothiophene carboxaldehyde (0.13 mmol). The reaction mixture was stirred at rt for 6 h, after which the solvent was removed under reduced pressure and the reaction mixture was further subjected to flash chromatography over silica gel using a gradient of 5:95 – 30:70 (MeOH:DCM saturated with ammonia) yielding N”-tert-butyl-4-(benzothiophen-3-yl)-4,5,6,7-tetrahydro-lH-imidazo[4,5- c]pyridine-2-ylcarbamate. (28.5 mg; 70%) as a white solid. 1H NMR (400 MHz, CDCl3) delta 7.94 (d, J = 7.7 Hz, IH), 7.85-7.81 (m, IH), 7.42-7.29 (m, 2H), 6.83 (s, IH), 5.86 (bs, IH), 5.57 (s, IH), 2.96 (ddd, J= 13.1, 5.9, 2.1 Hz, IH), 2.82 (ddd, J= 13.1, 10.3, 4.7 Hz, IH), 2.63-2.53 (m, IH), 2.43-2.35 (m, IH), 2.17 (bs, IH), 1.02 (s, 9H); 13C NMR (100 s MHz, CDCl3) delta 150.8, 150.0, 140.8, 137.9, 134.9, 124.4, 124.2, 124.1, 123.0, 122.2, 117.8, 85.1, 50.8, 38.6, 27.4, 25.8; ir (KBr) 3453, 2928, 1722, 1627, 1369, 1326, 1263, 1138, 835, 765, 734 cm”1; HRMS found [M+H]+ 371.1547, C19H23N4O2S requires 371.1542. To a stirred solution of this tetrahydro-intermediate (III) (0.15 mmol) in chloroform (10 mL) was added chloranil (0.30 mmol) and the reaction mixture refluxedo for 20 h. Solvent was removed on a rotary evaporator and the residue obtained further purified by flash chromatography over silica gel with a gradient of 5:95 – 15:85 (MeOH:DCM saturated with ammonia) giving pure 4-(benzothiophen-3-yl)taulH- imidazo[4,5-c]pyridin-2-amine (25.5 mg; 64%) as a white solid. 1H NMR (400 MHz, CD3OD) delta 8.29 (s, IH), 8.27 (d, J = 6.5 Hz, IH), 8.10-8.07 (m, IH), 7.79-7.75 (m, IH),s 7.60 (d, J = 6.5 Hz, IH), 7.55-7.48 (m, 2H); 13C NMR (100 MHz, CD3OD) delta 159.2, 158.8, 151.7, 141.7, 137.8, 135.8, 133.3, 126.9, 126.6, 124.2, 123.5, 117.4, 114.6, 109.0; HRMS found [M+H]+ 267.0706, C14H11N4S requires 267.0704.
5381-20-4 Thianaphthene-3-carboxaldehyde 227328, abenzothiophene compound, is more and more widely used in various.
Reference£º
Patent; MACQUARIE UNIVERSITY; WO2009/152584; (2009); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem