* 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.
Reference：
[1] Journal of the Chemical Society, 1908, vol. 93, p. 1998
2
[ 5439-08-7 ]
[ 5468-71-3 ]
Reference：
[1] Journal of the Chemical Society, 1908, vol. 93, p. 1998
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 21, p. 6348 - 6352
Example 1Preparation of 6-chloro-1-isopropyl-1H-imidazo[4,5-b]pyridin-2-ol; Example 1(a) 5-chloro-3-(isopropylamino)picolinamide: <strong>[5468-71-3]3,5-Dichloropicolinamide</strong> (50 mg, 0.26 mmol, 1.0 equiv) and isopropylamine (225 uL, 2.6 mmol, 1.0 equiv) were combined in a microwave vial equipped with a stirbar, sealed and heated to 200 C. for 30 min. The mixture was then dissolved in dichloromethane and loaded onto a Biotage caplet. Purification by silica gel MPLC (13%-68% Et2O/Hexanes) provided the desired compound as a white solid (31 mg, 56%). m/z=214.1 [M+H]+
General procedure: A 500-mL RBF was charged with 5-chloro-2-pyridinecarboxylic acid (Ark Pharm, 10.00 g, 63.5 mmol) and thionyl chloride (Aldrich, 100 ml, 1371 mmol). A catalytic amount of DMF (0.2 ml) was added and the reaction mixture was heated to 80 C under Argon atmosphere for 4 hours. The reaction mixture was cooled to RT and concentrated under reduced pressure. The residue was diluted with DCM (100 ml) and added slowly to a stirred solution of ammonium hydroxide (131 ml, 3364 mmol) at 0 C. After completed addition, the reaction mixture was allowed to stir an additional 10 min. The reaction mixture was concentrated under reduced pressure and the precipitate was filtered off. The solid was washed with water and dried to give the title compound (8.686 g, 55.5 mmol, 87 % yield) as an off-white solid. MS m/z=157 [M+H]+. Calculated for C6H5C1N20: 156
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
