* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With iodine; potassium hydroxide In N,N-dimethyl-formamide at 25℃; Cooling with ice
To a solution of 5-chloro-1H-pyrazolo[4,3-bjpyridine (XIII) (13 g, 84.7 mmol) in DMF (100 mL) was added iodine (43.0 g, 169 mmol) followed by potassium hydroxide powder (23.75 g, 423 mmol) portion wise under ice water cooling. The reaction mixture was stirred at 25°C overnight. The solid KOH was filtered off, washed with EtOAc, most of the DMF was removed under vacuum and the residue was diluted with water (200 mL) and extracted with 5 X 200 mL EtOAc, washed with brine (500 mL), dried over Na2504 and concentrated to give 5- chloro-3-iodo-1H-pyrazolo[4,3-bjpyridine (XIV) as an orange solid (23.5 g, 84.1 mmol, 99.3 percent yield). ESIMS found for C6H3C1TN3 mlz 279.9 (M+H).
99.3%
With iodine In N,N-dimethyl-formamide at 25℃; for 12 h; Cooling with ice
j0607j To a solution of 5-chloro-1H-pyrazolo[4,3-bjpyridine (XIII) (13 g, 84.7 mmol) in DMF (100 mL) was added iodine (43.0 g, 169 mmol) followed by potassium hydroxide powder (23.75 g, 423 mmol) portion wise under ice water cooling. The reaction mixture was stirred at 25°C overnight. The solid KOH was filtered off, washed with EtOAc, most of the DMF was removed under vacuum and the residue was diluted with water (200 mL) and extracted with EtOAc (5 x 200 mL), washed with brine (500 mL), dried over Na2504 and concentrated to give 5-chloro- 3-iodo-1H-pyrazolo[4,3-bjpyridine (XIV) as an orange solid (23.5 g, 84.1 mmol, 99.3 percent yield). ESIMS found for C6H3C1TN3 mlz 279.9 (M+H).
99.3%
With iodine; potassium hydroxide In N,N-dimethyl-formamide at 25℃;
To a solution of 5-chloro-lH-pyrazolo[4,3-b]pyridine (XIII) (13 g, 84.7 mmol) in DMF (100 mL) was added iodine (43.0 g, 169 mmol) followed by potassium hydroxide powder (23.75 g, 423 mmol) portion wise under ice water cooling. The reaction mixture was stirred at 25 °C overnight. The solid KOH was filtered off, washed with EtOAc, most of the DMF was removed under vacuum and the residue was diluted with water (200 mL) and extracted with EtOAc (5 x 200 mL), washed with brine (500 mL), dried over Na2SC>4 and concentrated to give 5-chloro- 3-iodo-lH-pyrazolo[4,3-b]pyridine (XIV) as an orange solid (23.5 g, 84.1 mmol, 99.3 percent yield). ESIMS found for C6H3C1IN3 mlz 279.9 (M+H).
99.3%
With iodine; potassium hydroxide In N,N-dimethyl-formamide at 25℃;
[0607] To a solution of 5-chloro-lH-pyrazolo[4,3-b]pyridine (XIII) (13 g, 84.7 mmol) in DMF (100 mL) was added iodine (43.0 g, 169 mmol) followed by potassium hydroxide powder (23.75 g, 423 mmol) portion wise under ice water cooling. The reaction mixture was stirred at 25°C overnight. The solid KOH was filtered off, washed with EtOAc, most of the DMF was removed under vacuum and the residue was diluted with water (200 mL) and extracted with EtOAc (5 x 200 mL), washed with brine (500 mL), dried over Na2S04 and concentrated to give 5-chloro- 3-iodo-lH-pyrazolo[4,3-b]pyridine (XIV) as an orange solid (23.5 g, 84.1 mmol, 99.3 percent yield). ESIMS found for C6H3C1IN3 mlz 279.9 (M+H).
91%
With iodine; sodium hydroxide In 1,4-dioxane at 90℃; for 18 h;
The mixture of 5-chloro-1H-pyrazolo [4, 3-b] pyridine (2.0 g, 13.02 mmol) , iodine (13.0 g, 52.1 mmol) and NaOH (12M, 11 mL, 130 mmol) in dioxane (20 mL) was stirred at 90 for 18 h. The reaction mixture was cooled to room temperature and extracted with ethyl acetate (20 mL x3) . The combined organic layers were washed with 10percentaqueous Na2S2O3(20 mLx2) , brine (20 mL) , dried over anhydrous Na2SO4, filtered off, and concentrated in vacuo. The crude product was purified by silica gel flash column chromatography eluting with hexanes/ethyl acetate (4: 11: 1) to give the title compound (3.3 g, 91percentyield) .
86%
With N-iodo-succinimide In N,N-dimethyl-formamide at 20℃; Inert atmosphere
5-Chloro-1 H-pyrazolo[4,3-/ ]pyridine (Preparation 1 a, 13.4 g, 0.09 mol) was dissolved in N,N- dimethylformamide (250 mL) and A/-iodosuccinimide (22.5 g, 0.10 mol) was added portionwise under argon atmosphere. The reaction mixture was stirred at room temperature overnight. Then more A/-iodosuccinimide (8.0 g) was added and the reaction was stirred at room temperature for 48 hours. The solvent was removed and the crude was suspended in water and extracted with ethyl acetate (x3). The combined organics were washed with a 10percent sodium thiosulfate aqueous saturated solution, water and brine, dried over anhydrous magnesium sulphate and concentrated under reduced pressure to yield the title compound (20.8 g, 86percent) as a solid. LRMS (m/z): 280, 282 (M+1 , M+3)+. -NMR δ (300 MHz, DMSO-d6): 7.49 (d, 1 H), 8.1 1 (d, 1 H).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
