Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → HCID 16661153, compound

Participants

Reaction Steps

A 25 mL round-bottomed flask was charged with 5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)nicotinaldehyde (500 mg, 1.54 mmol) and THF (10 mL). Methyl(triphenylphosphoranylidene)acetate (668 mg, 2.00 mmol) was added and the reaction was stirred at room temperature for 1 hour. An additional 668 mg of methyl(triphenylphosphoranylidene)acetate was added and the reaction was stirred overnight. The solids were filtered off and the filtrate was purified on a silica gel column (1:1 EtOAc:Hexanes) to afford (E)-methyl 3-(5-(benzyloxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)acrylate (450 mg, 76.8% yield) as a yellow foam. 1H NMR (CDCl3) 8.69 (s, 1H), 8.07 (d, 1H), 7.65 (d, 1H), 7.42 (m, 5H), 7.25 (m, 1H), 6.45 (m, 1H), 6.30 (d, 1H), 5.15 (s, 2H), 3.81 (s, 3H), 2.33 (s, 3H). Mass spectrum (apci) m/z=382.0 (M+H).

Provenance & Evidence