Tetrahydrofuran → HCID 57423219, compound

Participants

Reaction Conditions

Reaction Steps

n-BuLi 2.5 M in hexane (1.2 mL, 3 mmol, 3 eq) was added at −70° C. to a solution of the product from the previous step, N-{2-[(6-bromo-2-pyridinyl)oxy]ethyl}-N,N-dimethylamine (245 mg, 1 mmol) in dry THF (10 mL). The reaction mixture was stirred at −70° C. for 1 h 30 min. Ethyl formate (freshly distilled over P2O5) was added at −70° C., and the reaction mixture was stirred at −70° C. for 2 hours. The reaction was quenched with addition of water. The reaction mixture was extracted with 3 portions of DCM. Combined organic phase were dried with MgSO4, filtrated and evaporated to give the desired product, 6-[2-(dimethylamino)ethoxy]-2-pyridinecarbaldehyde (192 mg, 0.988 mmol, 99%).

Provenance & Evidence