3-Bromopyridine → HCID 63893930, compound

Participants

Reaction Steps

To an oven-dried flask was added anhydrous THF (20 mL) and 3-bromopyridine (2 mL, 20 mmol). Isopropylmagnesium chloride in THF (11 mL, 2.0 M solution) was then added dropwise over several minutes. The mixture was stirred at room temperature for 1 hour, and then 5-bromo-2-fluorobenzaldehyde (2.4 mL, 20 mmol) was added. After stirring for 1 further hour at room temperature, the reaction was quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc, dried over MgSO4, and purified by column chromatography (gradient 0 to 50% EtOAc in hexanes) to afford the product. 1H NMR (400 MHz, CDCl3) δ 8.51 (d, J=1.9 Hz, 1H), 8.41 (dd, J=4.8, 1.5 Hz, 1H), 7.78-7.68 (m, 2H), 7.38 (ddd, J=8.7, 4.6, 2.6 Hz, 1H), 7.27 (dd, J=8.6, 4.2 Hz, 1H), 6.95-6.85 (m, 1H), 6.10 (s, 1H), 4.22 (br s, 1H).

Provenance & Evidence