Sodium Carbonate → 5-(1-Isopropyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-carbaldehyde

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Reaction Conditions

Reaction Steps

To a stirred solution of 5-iodo-1-isopropylpyridin-2(1H)-one (0.41 g, 1.55 mmol) in toluene (5 mL) and ethanol (2 mL) was added 5-formylthiophen-2-yl boronic acid (0.289 g, 1.87 mmol), 2M Na2CO3 (0.495 g, 4.67 mmol), and Pd(PPh3)4 (0.09 g, 0.07 mmol). The mixture was purged with argon and heated at 100° C. for about 2 h. The mixture was concentrated, diluted with water (50 mL), and extracted with ethyl acetate (2×200 mL). The combined organic extracts were washed with brine solution (20 mL), dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by flash chromatography (silica gel, 60-120μ) using 20% ethyl acetate in hexane as eluent to afford 5-(1-isopropyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-carbaldehyde as an off-white solid (0.205 g, 53.3% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.18 (s, 1H), 7.99 (d, 1H), 7.78 (d, 1H), 7.62 (d, 1H), 7.58 (d, 1H), 7.53 (d, 1H), 5.08-5.01 (m, 1H), 1.21 (t, 6H), LC-MS m/z calcd for [M+H]+ 248.07. found 248.1.

Provenance & Evidence