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ChemicalBook CAS DataBase List 3-iodo-1H-indazole-6-carbaldehyde

3-iodo-1H-indazole-6-carbaldehyde synthesis

3synthesis methods
-

Yield: 81%

Reaction Conditions:

with iodine;potassium carbonate in N,N-dimethyl-formamide for 2 h;

Steps:


To a solution of lH-Indazole-6-carbaldehyde (2.00 g, 13.7 mmol), K2CO3 (3.79 g, 27.4 mmol) in DMF (15 mL) was added dropwise a solution of I2 (5.91 g, 23.3 mmol) in DMF (15 mL) and the reaction allowed to stir for two hours. An aqueous solution consisting Of Na2S2O4 (3.30 g) / K2CO3 (0.20 g) / H2O (30 mL) was then added and the solution stirred for one hour. The product was then precipitated by pouring the solution over ice-water (300 mL) and collected by vacuum filtration to give after drying 3.02 g, 81 % of a beige powder. 1H NMR (400 MHz, CD3OD) δ 10.11 (s, IH), 8.11 (s, IH), 7.74 (d, J= 8.34 Hz, IH), 7.62 (d, J= 8.34 Hz, IH); MS ESI 272.9 [M + H]+, calcd for [C8H5IN2O + H]+ 272.95.

References:

UNIVERSITY HEALTH NETWORK WO2009/79767, 2009, A1 Location in patent:Page/Page column 85