Diisopropylamine → 5-Bromo-2-fluoro-3-pyridinecarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (17 mL, 0.17 mol) in dry THF (200 mL) was added 2.5 M n-BuLi in hexane (68 mL, 0.17 mol) dropwise at 0° C. under N2 atmosphere. After the addition, the resulting mixture was cooled to −65° C. A solution of 5-bromo-2-fluoropyridine (25 g, 0.14 mol) in dry THF (100 mL) was then added dropwise. The resulting mixture was stirred at −65° C. for 90 minutes. Then ethyl formate (15.6 g, 0.21 mol) was added dropwise to the mixture. After stirred for 10 minutes, the reaction mixture was quenched with a solution of 10% citric acid in THF (100 mL) at −65° C. The resulting mixture was warmed up to room temperature, poured into water (100 mL) and extracted with EtOAc (200 mL). The organic layer was separated and washed with saturated aqueous NaCl (100 mL×2), dried over Na2SO4 and concentrated in vacuo to yield compound D-1-2 (25 g, 85%) as a yellow solid.

Provenance & Evidence