ChemicalBook CAS DataBase List 4,6-dichloro-1-Methyl-1H-iMidazo[4,5-c]pyridine

4,6-dichloro-1-Methyl-1H-iMidazo[4,5-c]pyridine synthesis

14synthesis methods

Product Name:4,6-dichloro-1-Methyl-1H-iMidazo[4,5-c]pyridine
CAS Number:887147-19-5
Molecular formula:C7H5Cl2N3
Molecular Weight:202.04

1H-Imidazo[4,5-c]pyridin-7-amine,4,6-dichloro-1-methyl-(9CI)

805316-72-7

887147-19-5

General procedure for the synthesis of 4,6-dichloro-1-methyl-1H-imidazo[4,5-c]pyridin-7-amine from 4,6-dichloro-1-methyl-1H-imidazo[4,5-c]pyridine: a solution of sodium nitrite (5.28 g, 76.5 mmol) in water (17 mL) was added dropwise over 5 min to a stirred 4,6-dichloro-1-methyl-1H-imidazo and [4,5-c]pyridin-7-amine (11.3 g, 52 mmol) solution of hypophosphorous acid (50 wt.% aqueous solution, 150 mL), keeping the reaction temperature between 0°C and 50°C. The reaction mixture was gradually warmed to room temperature and stirring was continued for 40 minutes. Subsequently, the mixture was cooled in an ice bath to between 0 °C and 50 °C, and the pH was adjusted to >10 by addition of aqueous sodium hydroxide (55 g dissolved in 100 mL of water). the resulting suspension was filtered, and the filter cake was washed with water and dried by suction to afford the product 4,6-dichloro-1-methyl-1H-imidazo[4,5-c]pyridine (9.9 g, 97% yield), which was analyzed for purity by high performance liquid chromatography ( HPLC) analyzing the purity was 99%, retention time was 0.92 min, and the molecular ion peak (M+H)+ detected by LC/MS was 202.06 (204.04,206.02).

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Yield:887147-19-5 100%

Reaction Conditions:

Stage #1: 7-amino-4,6-dichloro-1-methyl-1H-imidazo[4,5-c]pyridinewith sodium nitrite
Stage #2: with hypophosphorous acid at 100;

References:

Kempson, James;Guo, Junqing;Das, Jagabandhu;Moquin, Robert V.;Spergel, Steven H.;Watterson, Scott H.;Langevine, Charles M.;Dyckman, Alaric J.;Pattoli, Mark;Burke, James R.;Yang, XiaoXia;Gillooly, Kathleen M.;McIntyre, Kim W.;Chen, Laishun;Dodd, John H.;McKinnon, Murray;Barrish, Joel C.;Pitts, William J. [Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,# 10,p. 2646 - 2649] Location in patent:scheme or table