Sodium hydride → 8-chloro-5-vinyl-5H-chromeno[3,4-c]pyridine

To a stirred suspension of NaH (0.182 g, 7.58 mmol) in THF (30 mL) was added 1-(4-(4-chloro-2-fluorophenyl)pyridin-3-yl)prop-2-en-1-ol (0.5 g, 1.896 mmol) dissolved in THF (5 mL) and the reaction mixture was stirred at room temperature for 2 h. The reaction was quenched by addition of saturated aqueous ammonium chloride solution (5 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were washed with brine (1×10 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude 8-chloro-5-vinyl-5H-chromeno[3,4-c]pyridine was used without purification in the next step. 1H NMR (400 MHz, CDCl3) δ 8.61 (d, J=5.2 Hz, 1H), 8.40 (s, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.5 (d, J=5.2 Hz, 1H), 7.06 (d, J=2.2 Hz, 2H), 6.09 (m, 1H), 5.70 (d, J=6.2 Hz, 1H), 5.37 (m, 1H), 5.28 (m, 1H).

1. customThe reaction was quenched by addition of saturated aqueous ammonium chloride solution (5 mL)
2. extractionextracted with ethyl acetate (3×10 mL)
3. washThe combined organic extracts were washed with brine (1×10 mL)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe crude 8-chloro-5-vinyl-5H-chromeno[3,4-c]pyridine was used without purification in the next step

ORD record

ord-ff86c9a5c04f4c94aabd9e18219061f3

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703953B2