Skip to main content
. Author manuscript; available in PMC: 2010 Oct 31.
Published in final edited form as: Tetrahedron. 2009 Oct 31;65(44):8908–8915. doi: 10.1016/j.tet.2009.07.075

Table 1.

One-pot synthesis of indoles under Sonogashira coupling conditions.a

graphic file with name nihms151313u2.jpg
entry 1 R1 R2 Ar time (h)
 3 % yieldb
Step 1 Step 2
1 1a H C6H5 graphic file with name nihms151313t1.jpg 5 4 3a 82
2 1b Br graphic file with name nihms151313t2.jpg graphic file with name nihms151313t3.jpg 5 12 3j 83
a

Representative procedure: Step 1) 2-Iodoaniline 1 (0.500 mmol), terminal alkyne 2 (0.525 mmol), PdCl2(PPh3)2 (0.015 mmol), CuI (0.010 mmol), and 3 mL of Et3N were mixed in a sealed 4-dram vial. The reaction was stirred at room temperature for the indicated time. Step 2) Aryl iodide (0.550 mmol) and 3 mL of CH3CN were added to the reaction mixture of Step 1. The resulting mixture was stirred at 60 °C for the indicated time.

b

Isolated yields of indole product after column chromatography.