Table 1.

Reaction optimization for coupling of 1e with benzamide (2a) under various conditions^a.

Entry	Pd catalyst (5 mol %)	Ln	Base	Time (h)	Yield (%)b
1	Pd(OAc)2c	L1	Cs2CO3	2	95d
2	Pd2(dba)3	L1	Cs2CO3	5	90
3	Pd2(dba)3	L2	Cs2CO3	24	40
4	Pd2(dba)3	L3	Cs2CO3	24	40
5	Pd2(dba)3	L4	Cs2CO3	24	0
6	Pd(OAc)2	L2	Cs2CO3	24	45
7	Pd(OAc)2	L3	Cs2CO3	24	61
8	Pd(OAc)2	L1	K2CO3	4	83
9	Pd(OAc)2	L1	K3PO4	3	88

^aReactions of 1-benzyl-4-bromo-1H-pyrrolo[2,3-b]-pyridine (1e) (1.0 mmol) with benzamide (2a) (1.2 mmol) were performed in a sealed Schlenk tube at 100 °C in dioxane (2 mL) by using Pd catalyst (5 mol %), ligand (10 mol %) and base (1.5 mmol). ^bYields reported are isolated yields. ^cNo reaction occurred without palladium catalyst. ^dNo reaction occurred at room temperature.