4-(4-Chloro-2-fluorophenyl)nicotinaldehyde → 1-(4-(4-Chloro-2-fluorophenyl)pyridin-3-yl)prop-2-en-1-ol

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Reaction Steps

To a stirred solution of 4-(4-chloro-2-fluorophenyl)nicotinaldehyde (0.5 g, 2.122 mmol) (prepared as in Example 5, Part B) in THF (25 mL) at −70° C. was added vinylmagnesium bromide (1.0 M in THF) (6.37 mL, 6.64 mmol) dropwise and the solution was stirred at this temperature for 45 min. The reaction was quenched with saturated aqueous ammonium chloride solution (20 mL) and extracted with ethyl acetate (2×15 mL). The combined organic extracts were washed with brine (1×15 mL), dried over sodium sulfate and concentrated under reduced pressure. The crude product was used without purification in the next step. LCMS (ESI) m/e 264 [(M+H)+, calcd for C14H12ClFNO 264.0]; LC/MS retention time (Method C): tR=1.59 min.

Provenance & Evidence