Iodopyrazine → HCID 63968796, compound

Participants

Reaction Conditions

Reaction Steps

To an oven-dried flask was added anhydrous THF (60 mL) and 2-iodopyrazine (3 mL, 20 mmol). The flask was cooled to 0° C., and 2M n-butylmagnesium chloride in THF (11 mL) was then added dropwise over several minutes. The mixture was stirred at 0° C. for 30 minutes, and then 5-bromo-2-fluorobenzaldehyde (2.4 mL, 20 mmol) was added. After stirring for 2 hours at 0° C., 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 8.65 (s, 1H), 8.55 (s, 2H), 7.59 (dd, J=6.4, 2.5 Hz, 1H), 7.46-7.35 (m, 1H), 6.98 (t, J=9.2 Hz, 1H), 6.17 (s, 1H).

Provenance & Evidence