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

Temperature

100 °C

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.

1. customThe mixture was purged with argon
2. concentrationThe mixture was concentrated
3. additiondiluted with water (50 mL)
4. extractionextracted with ethyl acetate (2×200 mL)
5. washThe combined organic extracts were washed with brine solution (20 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under vacuum
8. customto obtain crude product
9. customThe crude product was purified by flash chromatography (silica gel, 60-120μ)

ORD record

ord-9c874faa0f8f4d088ca89cee9841679f

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09199975B2