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With hydrogenchloride; sodium nitrite; In water; at 0 - 20℃; for 3.08333h;
Synthesis 4-1 -A 3-Chloroisoquinoline 3-Aminoisoquinoline (1.44 g, 10 mmol) was suspended in 10M HCI (5 mL) and cooled to 0°C. Sodium nitrite (689 mg, 10 mmol) was added in portions over 5 minutes. The reaction mixture was stirred at 0°C for 2 hours and allowed to warm to room temperature over 1 hour. The reaction mixture was added carefully to saturated NaHCO3 solution (200 mL) and extracted into ethyl acetate. The insoluble byproduct was removed by filtration and the aqueous layer was re-extracted into ethyl acetate. The combined organics were washed with water and brine, dried (Na2SO4) and concentrated to a brown oil which solidified on standing. Flash chromatography on silica, eluting with dichloromethane, gave the title compound as a white solid (827 mg, 5.05 mmol, 51percent). 1H <n="96"/>NMR (Cl6-DMSO, 400 MHz) delta 9.12 (s, 1 H), 8.41 (s, 1 H), 8.12 (dd, 1 H, J = 7.5, 1.0 Hz), 7.93-7.90 (m, 1 H), 7.84-7.80 (m, 1 H), 7.74-7.70 (m, 1 H). LCMS (1) Rt = 1.79min; m/z (ESI+) 164 (MH+).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In Dimethyl ether; water; for 24h;Inert atmosphere; Reflux;
Compound A1 (5 mmol) and compound B1 (6 mmol) were weighed into a three-neck flask and Pd(pph3)4 (0.15 mmol) was added as a catalyst.K2CO3 (16 mmol) was added, vacuum was applied to the double-row tubes, nitrogen-filled vacuum was applied, and the mixture was recycled three times. Finally, the reaction system was protected with nitrogen.Add 15 mL each of dimethyl ether and water with a syringe and heat to reflux. The reaction was refluxed for 24 h and cooled to room temperature. After vortexing, the column was purified and product 11 was obtained.
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