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<strong>[34784-06-0]7-chloroisoquinoline</strong> (9 g, 55.0 mmol, 1.0 equiv)[mixture of 7-isoquinoline 3-5a and 8-isoquinoline 3-5b (a/b=3/2)]was dissolved in nitrobenzene (180 mL) and heated at 180 C. Bromine was added dropwise to this dark orange solution (3.11 ml, 60.5 mmol, 1.1 equiv.). The reaction mixture was stirred at 180 C. for 10 hours. LCMS showed that almost complete conversion. The reaction mixture was cooled to room temperature, 2M HCl in Et2O (30 mL) was added, followed by dilution with Et2O and Hexane. The precipitate was collected then taken up with EtOAc (200 mL), neutralized with saturated Na2CO3, and separated. The organic layer was dried over Na2SO4, filtered and concentrated. The crude residue was purified with silica gel chromatography (EtOAc/Hexane=0->30%) to give the title product 3-4. LRMS m/z (M+H) 242.2 found, 241.9 required.
With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃;
<strong>[953421-72-2]4-bromo-7-chloroisoquinoline</strong> (3-6)(1 g, 4.12 mmol, 1.0 equiv.) was dissolved in anhydrous CH2Cl2 (8.2 mL) and treated with mCPBA (1.622 g, 9.40 mmol, 2.3 equiv.). The reaction mixture was stirred at room temperature, forming 3-7 as a white precipitate. Following dilution with Et2O, the solid was collected and used without further purification in the next step. LRMS m/z (M+H) 260.1 found, 259.9 required.
With sodium azide; copper(II) sulfate heptahydrate; sodium carbonate; sodium L-ascorbate; L-proline; In water; N,N-dimethyl-formamide; at 85℃;Inert atmosphere;
General procedure: Under argon atmospherethe appropriate bromo isoquinolin (1 eq.), L-proline (0.1 eq.), sodiumazide (1.3 eq.) and sodium carbonate (1.3 eq.)was dissolved ina 2:1 mixture of DMF and water. Subsequently, sodium ascorbate(1.3 eq.) and copper sulfate hepta hydrate (1 eq.) were added andthe reaction mixture was stirred over night at 85 C. After fullconversion (LCMS control) the mixture was cooled to room temperatureand EtOAc and sat. aqueous NaHCO3 solution were added.The mixture was extracted with EtOAc (3x), the combined organiclayers were dried over sodium sulfate and concentrated underreduced pressure to obtain the crude. The obtained products wereused as obtained without further purification.
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