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With N-iodo-succinimide; In acetonitrile; at 75℃; for 18.5h;Inert atmosphere; |
A solution of the intermediate from Step A above (14.3g, 120mmol) and iV-iodosuccinimide (28.4g, 126mmoI) in acetonitrile (210 mL) was heated at 75 °C. After 17 hours, N- iodosuccinimide (5.4g, 24mmol) was added and the reaction solution stirred at 75 °C for an additional 1.5 hours. The reaction solution was cooled to room temperature and diluted with water. The slurry was concentrated in vacuo to remove most of the acetonitrile. The solid was collected, washed with water, and dried under a vacuum with a nitrogen sweep for 17 hours to give the title compound. NMR (400 MHz, CH CN-d3): delta 11.85 (s, 1 H); 8.55 (dd, J = 4.53,1.53 Hz, 1 H); 7.87 (dd, J = 8.1 1, 1.53 Hz, 1 H); 7.24 (dd, J = 8.1 1, 4.51 Hz, 1 H). m/z = 246.1 (M+H). |
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With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 1h;Cooling with ice; |
(2); Compound 2 (12.2 g) was dissolved in DMF (200 ml), and then thereto was added potassium hydroxide (26.86 g) with stirring under ice-cooling, then added gradually iodine (52.24 g), and then the mixture was warmed slowly to room temperature, and stirred at room temperature for an hour. The reaction mixture was poured into 10percent aqueous sodium hydrogen sulfite solution (1 L), and the precipitated crystals were filtered, washed with water, and then dried to give Compound 3 (21.07 g) as pale yellow crystals.MS (APCI) 246 [M+H]+ |
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With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 16h; |
A. 3-lodo-I H-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong>To a solution of iH-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong> (2.00 g, i6.8 mmol) in DMF (35 mL) were added iodine (6.39 g, 25.2 mmol) and potassium hydroxide (2.35 g, 42.0 mmol). The reaction mixture was stirred at RT for i6 h. The mixture was diluted with iOpercent sodium thiosulfate and water and the resulting suspension was filtered to give the title compound as a yellow powder. TLC, R (EtOAc) = 0.8; MS (UPLCMS): 246.0 [M+H]+, 243.9 [M-H]-; tR (HPLC conditions f): i .3i mm. |
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With N-iodo-succinimide; In acetonitrile; at 75℃; for 17h; |
Compound (M-1) (100 mg, 0.839 mmol) was dissolved in acetonitrile (2.8 mL), NIS (208 mg, 0.923 mmol) wasadded and the mixture was stirred at 75°C for 17 hr. The reaction mixture was allowed to cool, ethyl acetate was added,and the mixture was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, andfiltered. The solvent was evaporated under reduced pressure to give compound (M-2) |
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With N-iodo-succinimide; In acetonitrile; at 75℃; for 17h; |
Compound (M-1) (100 mg, 0.839 mmol) was dissolved in acetonitrile (2.8 mL)NIS (208 mg, 0.923 mmol) was added,And the mixture was stirred at 75 ° C. for 17 hours.The reaction solution was allowed to cool, ethyl acetate was added, water,And then washed successively with saturated brine,After drying with anhydrous sodium sulfate, filtration was carried out.By distilling off the solvent under reduced pressure,To obtain a compound (M-2). |
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