Triethylamine → tert-Butyl 2-(diethoxymethyl)-1h-pyrrolo[3,2-c]pyridine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

Heat a solution of (3-iodo-pyridin-4-yl)carbamic acid 1,1-dimethylethyl ester (13.3 g, 41.56 mmol, Darnbrough, Shelley; Mervic, Miljenko; Condon, Stephen M.; Burns, Christopher J. Synthetic Communications (2001) 31(21), 3273-3280), 3,3-diethoxy-1-propyne (5.96 ml, 41.56 mmole), triethylamine (23 ml, 166 mmol), dichlorobis(triphenyl-phospine)palladium(II) (1.46 g, 2.08 mmol) and copper iodide (237 mg, 1.25 mmol) in dry DMF under argon to 90° C. for 3 h. Allow the reaction mixture to cool to 70° C. and add DBU (12.5 ml, 83.12 mmol). Stir the reaction at 70° C. for 3 h and then stir at room temperature overnight. Pour the reaction mixture into EtOAc, wash with water (2×) and brine, dry over MgSO4, filter and concentrate to give the title compound as an oil. Purify the oil by flash chromatography (silica, elute with 10-20% EtOAc/n-heptane) to provide 9.8 g of the title compound as a clear oil, tlc (silica, 30% EtOAc/heptane, Rf=0.30).

Provenance & Evidence