HCID 88575710, compound → HCID 66692552, compound

Participants

Reaction Steps

To a solution of benzyl (2E)-2-([(benzyloxy)carbonyl]imino)-6-(2-[methoxy(methyl)amino]-2-oxoethyl)pyridine-1(2H)-carboxylate (150 mg, 0.33 mmol) in 4 ml anhydrous THF cooled to −40° C. via dry ice/acetone bath under nitrogen atmosphere was added via syringe 1.0M vinylmagnesium bromide (1.5 mL, 1.5 mmol) and the resulting solution stirred for 2 hours allowing to warm to room temperature. The reaction was quenched with water and extracted with ethyl acetate (3×10 mL). The organics were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via preparative TLC plate (1000 μM) eluting with 2.5% methanol in dichloromethane to afford the title compound (64 mg, 67%). LC-MS: C17H16N2O3 calculated 296.32 found m/z (ES) 297.3 (MH)+. 1HNMR (500 MHz, DMSO) δ: 10.12 (s, 1H) 8.05 (d, J=8.5 Hz, 1H), 7.99 (d, J=2.1, 1H), 7.62 (dd, J=2.2, 8.7 Hz, 1H), 7.60-7.34 (m, 5H), 6.40 (dd, J=10.3, 17.7 Hz, 1H), 6.26 (dd, J=10.3, 18.1 Hz, 1H), 5.94 (d, J=10.3 Hz, 1H), 5.22 (s, 2H), 3.60 (s, 2H).

Provenance & Evidence