2-Dimethylaminopyridine → HCID 18975311, compound

Participants

Reaction Steps

To a solution of 3-formyl-5-(1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridine (1.1 g, 5.2 mmol) in acetonitrile (30 mL) was added di-tert-butyldicarbonate (1.69 g, 7.8 mmol) and dimethylaminopyridine (63 mg, 0.52 mmol) and the mixture was stirred at ambient temperature under nitrogen for 16 hours. The solvent was evaporated in vacuo and the residue chromatographed on silica eluting with a gradient of 2 to 5% MeOH in DCM to give a yellow solid. This was triturated with ether. The precipitate was collected by filtration to afford the title compound (0.71 g, 49%) as a cream solid. mp 170° C. (dec.). 1H NMR (360 MHz, d4 -MeOH) δ 1.76 (9H, s), 8.49 (1H, s), 8.80 (1H, s), 9.29 (2H, s), 9.34 (1H, s) and 10.12 (1H, s).

Provenance & Evidence