Water → HCID 58286923, compound

Participants

Reaction Steps

2-Fluoro-6-(2-oxo-propyl)-benzoic acid (12.33 g, 31.43 mmol) and 3-aminopyridine (5.12 g, 54.4 mmol) in 25 mL dioxane were refluxed overnight. The reaction mixture was poured into water (250 mL). The mixture was extracted with ethyl acetate (200 mL). The organic phase was washed with brine, dried over MgSO4 and filtered through a pad of silica gel. The silica gel pad was washed with 250 mL ethyl acetate. The organic fractions were combined and rotavaped. The crude product was flash chromatographed on silica gel (eluent: 50% heptane/ethyl acetate to ethyl acetate) to obtain the product as a pale pink solid (1.3 g, yield 16.3%). LC-MS (m/z) 255.5 (MH+); tR=0.64. 1H NMR (500 MHz, CDCl3): 1.99 (s, 3H, Me), 6.43 (s, 1H), 7.07 (dd, J=8.12 Hz, J=11.3 Hz, 1H), 7.24 (d, J=7.9 Hz, 1H), 7.49 (dd, J=4.9 Hz, J=8.1 Hz, 1H), 7.58 (td, J(d)=4.8 Hz, J(t)=8 Hz, 1H), 7.64 (unresolved dt, J(d)=8.1 Hz, J(t)=ca. 1.5 Hz, 1H), 8.53 (d, J=2 Hz, 1H), 8.71 (d, J=4.8 Hz, J=0.9 Hz, 1H).

Provenance & Evidence