Toluene → HCID 73503327, compound

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Reaction Steps

A solution of 1-tert-butyloxycarbonyl-3-formyl-5-(1,2,4-triazol-4-yl)pyrrolo[2,3-c]pyridine (0.71 g, 2.3 mmol) and (carboethoxymethylene)triphenylphosphorane (0.95 g, 2.7 mmol) in toluene (25 mL) was heated at 80° C. under nitrogen for 2 hours. The mixture was allowed to cool and the solvent evaporated in vacuo. The residue was chromatographed on silica eluting with 20% EtOAC in DCM, followed by a gradient of 2 to 5% MeOH in DCM to afford ethyl 3-[1-tert-butyloxycarbonyl-5-(1,2,4-triazol-4-yl)pyrrolo[2,3-c]pyridin-3-yl]prop-2-enoate (0.93 g), contaminated with minor impurities, as a cream solid. 1H NMR (360 MHz, CDCl3) δ 1.38 (3H, t, J=7.1Hz), 1.73 (9H, s), 4.32 (2H, q, J=7.1Hz), 6.51 (1H, d, J=16.2Hz), 7.76 (1H, s), 7.80 (1H, d, J=15.7Hz), 8.09 (1H, s), 8.95 (2H, s) and 9.33 (1H, s). This was used without further purification.

Provenance & Evidence