反应详情

温度

90 °C

To a mixture of 5-bromofuran-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, PREPARATION 2, 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)furan-2-carbaldehyde (1.2 g, 103% yield). MS: m/e=246 (M+H). 1H-NMR (CDCl3, δ ppm) 9.64 (s, 1H), 7.79 (s, 1H), 7.33 (d, 1H, J=3.8 Hz), 6.67 (d, 1H, J=3.8 Hz); 3.99 (s, 3H); 2.64 (s, 3H); 2.61 (q, 2H, J=7.6 Hz), 1.21 (t, 3H, J=7.6 Hz).

1. temperatureThe reaction is cooled
2. washwashed with water
3. customThe organic layer is separated
4. customdried
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue is purified by flash chromatography
8. washeluting with heptane-30% ethyl acetate