2-(pyridin-4-yl)thiazole-4-carbaldehyde synthesis

Yield:533885-37-9 69%

Reaction Conditions:

Stage #1: ethyl 2-(4-pyridyl)-1,3-thiazole-4-carboxylatewith diisobutylaluminium hydride in dichloromethane at 0; for 1 h;
Stage #2: with acetic acid in dichloromethane at 0 - 25;

Steps:

270.270B

Example 270B; 2- (4-pyridinyl)-1, 3-thiazole-4-carbaldehyde; Example 270A (4.7 g, 20.1 mmol) was dissolved in dichloromethane (67 mL) and treated with the slow addition of a 1 M solution of diisobutylaluminum hydride in dichloromethane (38 mL, 1.9 equivalents). The reaction was stirred under a nitrogen atmosphere for 1 h. , followed by addition of acetic acid (3.8 mL). The reaction was warmed to 25°C, quenched with a 10% solution of sodium potassium tartrate (200 mL), and stirred for 1 h. The layers were separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and the solvent was removed by evaporation to give 3.73 g crude material which was purified using chloroform : ethyl acetate (1: 1) to give 2.62 g (69%) of the title compound.

References:

WO2005/61487,2005,A1 Location in patent:Page/Page column 156-157