Cesium carbonate → HCID 86709753, compound

Participants

Reaction Steps

An oven-dried microwave vial was evacuated and backfilled with argon. The vial was charged with Pd(OAc)2 (25 mg 0.113 mmol, 10 mol % Pd), BINAP (112 mg, 0.17 mmol, 15 mol %), and Cs2CO3 (733 mg, 2.25 mmol) and evacuated and backfilled with argon. The flask was capped with a rubber septum, and dry dioxane (6 mL), 1-chloronaphthalen-2-yl trifluoromethanesulfonate (350 mg, 1.13 mmol), and tert-butyl (2-aminoethyl)carbamate (361 mg, 2.25 mmol) were added through the septum. Then, the reaction vial was sealed and placed in the microwave reactor and irradiated for 2 h at 150° C. until the starting materials had been completely consumed as judged by TLC and GC analysis. The crude product was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 99:1 to 90:10 as eluent) to afford tert-butyl {2-[(1-chloronaphthalen-2-yl)amino]ethyl}carbamate as a whitish solid in 48% yield.

Provenance & Evidence