Potassium Carbonate → Ethyl 3-(5-(3-chloro-2-formyl-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Participants

Reaction Conditions

Reaction Steps

2-Bromo-6-chloro-4-(trifluoromethyl)benzaldehyde (3.4 g, 11.9 mmol) (as described in Example 72, STEP C), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (5.0 g, 14.3 mmol), Pd(dppf)Cl2 (435 mg, 0.6 mmol), and 2 M K2CO3 (aq) (11.9 mL, 23.8 mmol) were dissolved in 1,4-dioxane (48 mL) and heated to 90° C. After 2 h the temperature was lowered to 80° C. After 14 h the resulting mixture was concentrated, diluted with EtOAc and 4M aqueous NaCl, and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organics were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Provenance & Evidence