| 97% |
With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100℃; for 4h; |
5-Bromoisoquinoline (8 g, 38.65 mmol) and dimethyl formamide (100 mL) were mixed and stirred. The reaction solution was added with Zn(CN)2 (2.72 g, 23.19 mmol) and Ph(PPH)4 (1.78 g, 1.55 mmol), followed by stirring for about 4 hours at 100C. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The resulting organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound (5.8 g, 97 %). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 9.45 (s, 1H), 8.72 (d, 1H), 8.50 (d, 1H), 8.39 (d, 1H), 7.94 (d, 1H), 7.85 (t, 1H). MS (ESI+, m/z): 155 [M+H]+ |
| 97% |
With Ph(PPH)4; In N,N-dimethyl-formamide; at 100℃; for 4h; |
5-Bromoisoquinoline (8 g, 38.65 mmol) and dimethyl formamide (100 mL) were mixed and stirred. The reaction solution was added with Zn(CN)2 (2.72 g, 23.19 mmol) and Ph(PPH)4 (1.78 g, 1.55 mmol), followed by stirring for about 4 hours at 100 C. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The resulting organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound (5.8 g, 97%). 1H-NMR Spectrum (300 MHz, DMSO-d6): δ 9.45 (s, 1H), 8.72 (d, 1H), 8.50 (d, 1H), 8.39 (d, 1H), 7.94 (d, 1H), 7.85 (t, 1H). MS (ESI+, m/z): 155 [M+H]+ |
| 24 g |
With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100℃; for 2h;Inert atmosphere; |
To a solution (degassed with nitrogen) of intermediate 2 (45 g, 216 mmoles) in DMF (450 mL) there are added Zn(CN)2 (30 g) and Pd(PPh3)4(9.8 g). The mixture is heated at 100 C. for 2 hours. After return to ambient temperature, the mixture is taken up in AcOEt (200 mL) and water (2 L). The mixture is brought to pH>8 by addition of a 20% aqueous NaOH solution. After addition of AcOEt (200 mL), the organic phase is recovered by decantation, filtered over Celite, washed with a saturated aqueous NaCl solution and then dried over MgSO4 before being concentrated in vacuo. The solid is ground and dried in vacuo and taken up in a 1N aqueous HCl solution (1 L), and the acidic aqueous phase is washed with AcOEt and then treated with a 20% aqueous NaOH solution, the precipitate that forms is collected and dissolved in methylene chloride. The solution is dried over MgSO4, and evaporation in vacuo yields intermediate 653 in the form of a beige solid (24 g). 1H NMR (400 MHz; DMSO-d6): δ 9.53 (s, 1H), 8.76 (d, 1H), 8.54 (d, 1H), 8.45 (d, 1H), 7.96 (d, 1H), 7.87 (t, 1H). IR (cm-1): 2226. |
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