Dimethylformamide → HCID 58259055, compound

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask, (5-bromo-pyridin-2-yl)-(2-fluoro-benzyl)-amine (40, 3.90 g, 13.9 mmol) was combined with 60.0 mL of tetrahydrofuran at −78° C. under nitrogen and tert-butyllithium (5.57 mL, 2.50 M in hexane) was added over 5 minutes. After 30 minutes additional tert-butyllithium (17.1 mL, 1.7 M in hexane) was added over 5 minutes. After 25 minutes, N,N-dimethylformamide (2.6 mL, 34 mmol) was added and the mixture was stirred for 70 minutes at −78° C., then allowed to warm up to room temperature for 1 hour. The reaction was poured into aqueous ammonium chloride and extracted with ethyl acetate. The organic portion was dried with sodium sulfate, filtered and filtrate concentrated under vacuum to provide the desired compound (41, 3.0 g), which was used in the next step without further purification.

Provenance & Evidence