3-Methoxy-2-(4-Methyl-1H-Imidazol-1-Yl)-5-Nitropyridine(WX609390) synthesis

Yield: 74%

Reaction Conditions:

with potassium carbonate in dimethyl sulfoxide at 20 - 45;

Steps:

43b
Example 43 b. 3-methoxy-2-(4-methyl-lH-imidazol-l-yl)-5-nitropyridine To a suspension of 4-methyl-lH-imidazole (0.522 g, 6.36 mmol) and potassium carbonate (1.832 g, 13.26 mmol) in DMSO (20 mL) at room temperature was added 2-chloro-3- methoxy-5-nitropyridine (1.0 g, 5.30 mmol). The reaction mixture was stirred at 45°C overnight. About 20 mL warm water (heated to 50⁰C) was added to the reaction mixture and the precipitated solid was immediately filtrated and washed with warm water. The solid was dried in the dry vacuum oven at 40⁰C for two days giving 0.914 g of the title compound as an isomeric mixture (74 % Yield). 1H NMR (400 MHz, DMSO-J₆) δ ppm 8.90 - 8.94 (m, 1 H), 8.45 (s, 1 H), 8.32 - 8.37 (m, 1 H), 7.66 - 7.70 (m, 1 H), 4.10 (s, 3 H), 2.15 - 2.20 (m, 3 H). MS m/z 235 [M+H] ⁺.

References:

ASTRAZENECA AB;LO-ALFREDSSON, Yvonne;PAULSEN, Kim;RAKOS, Laszlo;ROTTICCI, Didier;WALDMAN, Magnus WO2010/132015, 2010, A1 Location in patent:Page/Page column 122-123