Toluene → HCID 67689969, compound

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Reaction Steps

A solution of 1-tert-butyloxycarbonyl-3-formyl-5-(1,2,4-triazol-1-yl)pyrrolo[2,3-c]pyridine (1.5 g, 4.8 mmol) and (carboethoxymethylene)triphenylphosphorane (2.0 g, 5.8 mmol) in toluene (30 mL) was heated at 80° C. under nitrogen for 90 min. The mixture was allowed to cool and the solvent was evaporated in vacuo. The residue was chromatographed on silica eluting with 20% EtOAc in DCM to give a colourless solid. This was triturated with ether and the solid rechromatographed on silica with 20% EtOAc in DCM to give the title compound (1.77 g, 96%) as a colourless solid. mp 178°-181° C. 1H NMR (360 MHz, CDCl3) δ 1.37 (3H, t, J=7.1Hz), 1.73 (9H, s), 4.31 (2H, q, J=7.1Hz), 6.59 (1H, d, J=16.2Hz), 7.81 (1H, d, J=16.2Hz), 8.03 (1H, s), 8.14 (1H, s), 8.30 (1H, s), 9.21 (1H, s) and 9.26 (1H, br s).

Provenance & Evidence