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With iodine; potassium hydroxide In N,N-dimethyl-formamide at 1 - 40℃; for 1h;
48.1 (1) Synthesis of 6-bromo-3-iodo-1H-indazole [36-1] (hereinafter referred to as a compound [36-1])
General procedure: (1) Synthesis of 6-bromo-3-iodo-1H-indazole [36-1] (hereinafter referred to as a compound [36-1]) To a solution of 6-bromo-1H-indazole (1.11 g) in N,N-dimethylformamide (10 mL) were added iodine (2.17 g) and potassium hydroxide (1.14 g), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was quenched with water, and extracted with chloroform. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (1.45 g) as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ: 11.22 (1H, s), 7.71 (1H, s), 7.39-7.31 (2H, m).
2
[ 1305208-17-6 ]
[ 2640092-74-4 ]
Yield
Reaction Conditions
Operation in experiment
Multi-step reaction with 2 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C
1.2: 2 h / 0 - 20 °C
2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium phosphate / water; 1,4-dioxane / 1 h / 70 °C / Inert atmosphere
Stage #1: 6-bromo-3-iodo-1H-pyrazolo[4,3-b]pyridine With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h;
Stage #2: trityl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;
34.2 Step 2.
Step 2. 6-Bromo-3-iodo-1-trityl-1H-pyrazolo[4,3-b]pyridine To a suspension of NaH (1.63 g, 40.8 mmol) in DMF (100 ml) at 0° C. was added a solution of 6-bromo-3-iodo-1H-pyrazolo[4,3-b]pyridine (12.0 g, 37.0 mmol) in 20 ml of DMF dropwise. After the addition was complete, the reaction mixture was warmed to r.t and stirred at that temperature for 30 min. The mixture was then cooled back to 0° C. and treated with a solution of (chloromethanetriyl)tribenzene (11.4 g, 40.8 mmol) in 20 ml of DMF. The reaction mixture was stirred at r.t for 2 h. Water was then added and the product was extracted with DCM. The organic phase was concentrated in vacuo. The resultant solid was collected by filtration and air-dried. LC-MS calculated for C25H18BrIN3 (M+H)+: m/z=566.0; found 566.0.
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; for 2h;
34.1 Step 1.
Step 1. 6-Bromo-3-iodo-1H-pyrazolo[4,3-b]pyridine To a solution of 6-bromo-1H-pyrazolo[4,3-b]pyridine (8.0 g, 40.4 mmol) in 60 ml of DMF was added 1-iodopyrrolidine-2,5-dione (7.69 g, 44.4 mmol), and the reaction mixture was stirred at r.t for 2 h. The mixture was poured into water (300 ml) and was stirred for another 10 min. The resulting solid was collected by filtration and was washed with water. It was air-dried and used in the next step without further purification. LC-MS calculated for C6H4BrIN3 (M+H)+: m/z=323.9; found 323.9.
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