Dimethylformamide → 5-(5-Ethyl-6-methoxy-2-methylpyridin-3-yl)thiophene-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5-bromothiophene-2-carbaldehyde (1.25 g, 7.14 mmol), 3-ethyl-2-methoxy-6-methyl-5-(4,4,5,5-tetramethyl-[1,3,2-dioxaborolan-2-yl)pyridine (1.32 g, 4.76 mmol) prepared in accordance with one of the procedures of Step 1, potassium carbonate (2.63 g, 7.14 mmol) and dimethylformamide (30 mL) under a nitrogen atmosphere is added dichloro[1,1′-bis(diphenylphosphino)ferrocene]-palladium dichloromethane adduct (0.2 g, 6 mol %) and the mixture is stirred at 90° C. for 2 hr. The reaction is cooled, diluted with water and washed with water. The organic layer is separated, dried, filtered and concentrated. The residue is purified by flash chromatography eluting with heptane-30% ethyl acetate to afford 5-(5-ethyl-6-methoxy-2-methylpyridin-3-yl)thiophene-2-carbaldehyde (1.2 g, 103% yield).

Provenance & Evidence