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ChemicalBook CAS DataBase List 3-b]pyridine

3-b]pyridine synthesis

4synthesis methods
-

Yield: 99.3%

Reaction Conditions:

with iodine;potassium hydroxide in N,N-dimethyl-formamide at 25;Cooling with ice;

Steps:

1
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 % yield). ESIMS found for C6H3C1TN3 mlz 279.9 (M+H).

References:

SAMUMED, LLC.;KC, Sunil Kumar;WALLACE, David Mark;CAO, Jianguo;CHIRUTA, Chandramouli;MARAKOVITS, Joseph Timothy;BOLLU, Venkataiah;HOOD, John WO2017/23989, 2017, A1 Location in patent:Paragraph 0606; 0607