1-Butanol → HCID 57884143, compound

Participants

Reaction Steps

2-Fluoro-N-phenethyl-nicotinamide (196 mg, 0.802 mmol), n-butanol (700 μL, 7.65 mmol) and potassium bis(trimethylsilyl)amide (2.5 mL, 0.5 M in toluene) were combined and stirred for 5 minutes at room temperature. The reaction mixture was evaporated to dryness and purified by column chromatography on silica gel using a gradient of 0-20% ethyl acetate in hexanes. The pure fractions were combined and evaporated to dryness to yield a colorless oil (207 mg, 0.694 mmol, 86.5%). ESI-MS m/z calc. 298.2, found 299.2 (M+1)+. Retention time of 3.46 minutes. H NMR (400 MHz, CD3CN) δ, 0.95 (t, J=7.4 Hz, 3H), 1.34-1.44 (m, 2H), 1.63-1.70 (m, 2H), 2.91 (t, J=7.0 Hz, 2H), 3.65-3.73 (m, 2H), 4.41 (t, J=6.7 Hz, 2H), 7.08 (dd, J=7.5, 4.8 Hz, 1H), 7.23-7.37 (m, 5H), 8.01 (s, 1H), 8.25 (dd, J=4.8, 2.0 Hz, 1H), 8.39 (dd, J=7.5, 2.0 Hz, 1H).

Provenance & Evidence