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. Author manuscript; available in PMC: 2014 Nov 6.
Published in final edited form as: J Am Chem Soc. 2013 Oct 24;135(44):10.1021/ja408917n. doi: 10.1021/ja408917n

Scheme 3. Synthesis of the 2-Cyanobenzofurans.

Scheme 3

Reagents: (a) PPh3, CBr4, DCM, 0°C → RT, 2 h; (b) CuI, K2CO3, 80 °C, 4 h; (c) NaCN, DMSO, 100 °C, 24 h; (d) CuI, Cs2CO3N,N-dimethylglycine hydrochloride, dioxane, 90 °C, 18 h; (e) BBr3, DCM, −78 °C → 0 °C, 3 h; (f) 3-benzoyl,1-bromoethyluracil, Cs2CO3 or K2CO3, DMF, 60 °C, 3 h; (g) NH4OH, DCM, 16 h.