With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.34784-04-8,5-Bromoisoquinoline,as a common compound, the synthetic route is as follows.
To a solution of n-butyllithium (19.3 mL of 2.5 M in hexanes, 48 mmol) in a mixture of ether (80 mL) and THF (80 mL) at -78¡ã C. was added dropwise a solution of bromoisoquinoline (5.0 g, 24 mmol) in THF (10 mL). The reaction mixture was stirred at -78¡ã C. under argon for 30 minutes. Following the general procedures described by Pearson, et al., in J. Heterocycl. Chem., Vol. 6 (2), pp. 243-245 (1969), a solution of DMF (3.30 g, 45 mmol) in THF (10 mL) was cooled to -78¡ã C. and quickly added to the isoquinolyllithium solution. The mixture was stirred at -78¡ã C. for 15 minutes. Ethanol (20 mL) was added followed by saturated NH4Cl solution. The resulting suspension was warmed to room temperature. The organic layer, combined with the ether extraction layer, was dried over Na2SO4. A pale yellow solid (2.4 g, 15 mmol, 64percent yield) was obtained from chromatography (SiO2 Type-H, 50percent EtOAc in hexanes) and recrystallization (ethanol): mp 114-116¡ã C.; 1H NMR (DMSO-d6) delta 10.40 (s, 1H), 9.44 (s, 1H), 8.85 (d, 1H, J=6.0 Hz), 8.69(d, 1H, J=6.0 Hz), 8.45 (m, 2H), 7.90 (t, 1H, J=7.2 Hz); 13C NMR (DMSO-d6) delta 194.23, 153.5, 146.2, 140.2, 135.2, 132.6, 130.2, 128.6, 127.5, and 117.2. Anal. Calcd. for C10H7NO.0.05H2O: C, 75.99; H, 4.53; N, 8.86. Found: C, 75.98, H, 4.66; N, 8.68., 34784-04-8
The synthetic route of 34784-04-8 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; DarPharma, Inc.; US2007/155720; (2007); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem