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. 2012 Nov 19;8:2004–2018. doi: 10.3762/bjoc.8.227

Table 7.

Optimization of the coupling reaction of N-methyl-4-bromo-7-azaindole (1c) with m-cresol (8a).a

graphic file with name Beilstein_J_Org_Chem-08-2004-i081.jpg
Entry Pd catalyst (5 mol %) Ln Base Solvent Time (h) Yield (%)b
1 Pd(OAc)2 L1 Cs2CO3 dioxane 5 20
2 Pd(OAc)2 L1 K2CO3 dioxane 3 30
3 Pd(OAc)2 L1 K2CO3 dioxane 10 70
4 Pd(OAc)2 L1 K2CO3 THF 10 50
5 Pd2(dba)3 L1 Cs2CO3 dioxane 3 10
6 Pd2(dba)3 L1 K2CO3 dioxane 10 32
7 Pd(OAc)2 L2 Cs2CO3 dioxane 24 45
7 Pd(OAc)2 L3 Cs2CO3 dioxane 24 61
9 Pd(OAc)2 L1 K2CO3 dioxane 12 68
10 Pd(OAc)2 L1 K2CO3 dioxane 24 65

aReaction conditions: N-methyl-4-bromo-7-azaindole (1c) (1.0 mmol), m-cresol (1.2 mmol), base (3.0 mmol), palladium catalyst (5 mol %), ligand (10 mol %), and 2 mL of dioxane, 100 °C, 3–24 h. bYields reported are isolated yields.