4-Thiazolecarboxaldehyde, 2-(2-pyridinyl)- synthesis

Yield: 53%

Reaction Conditions:

Stage #1:ethyl-2-(pyridin-2-yl)-thiazole-4-carboxylate with diisobutylaluminium hydride in dichloromethane at -78; for 1 h;
Stage #2: with acetic acid in dichloromethane at -78 - 25;
Stage #3: with Rochelle's salt in dichloromethane;water at 25; for 1 h;

Steps:

3.J
A solution containing the product of Example 31 (0.91 g, 3.9 mmol) in dichloromethane (13 mL) was treated dropwise with DIBAL (7.4 mL, 1 M in dichloromethane) at -78° C., stirred at -78° C. for 1 hour, treated with acetic acid (0.8 mL) and warmed to 25° C. A 10% solution of aqueous sodium potassium tartrate was treated with and the mixture was stirred vigorously for 1 hour. The reaction mixture was partitioned between chloroform and water, and the organic phase phase was washed with brine, dried over MgSO₄, filtered and concentrated. The residue was chromatographed on silica gel eluting with with 0-10% ethyl acetate in dichloromethane to give the title compound (0.39 g, 53% yield).

References:

DeGoey, David A.;Flentge, Charles A.;Flosi, William J.;Grampovnik, David J.;Kempf, Dale J.;Klein, Larry L. US2005/131017, 2005, A1 Location in patent:Page/Page column 97