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

Table 2.

C–N-bond-formation cross coupling of N-protected 4-bromo-7-azaindoles 1 with amides 2.

graphic file with name Beilstein_J_Org_Chem-08-2004-i002.jpg

Entry 7-Azaindole 1 Amide 2 Product 3a Time (h) Yield (%)b

1 Inline graphic
1a
Inline graphic
2a
24 NRc
2 Inline graphic
1b
Inline graphic
2a
5 0d
3 Inline graphic
1c
Inline graphic
2a
Inline graphic
3a
2 95
4 Inline graphic
1c
Inline graphic
2b
Inline graphic
3b
3 85
5 Inline graphic
1c
Inline graphic
2c
Inline graphic
3c
2.5 92
6 Inline graphic
1d
Inline graphic
2d
Inline graphic
3d
3 91
7 Inline graphic
1d
Inline graphic
2e
Inline graphic
3e
3 89
8 Inline graphic
1d
Inline graphic
2f
Inline graphic
3f
3 85
9 Inline graphic
1e
Inline graphic
2a
Inline graphic
3g
2 95

aReactions of N-protected 7-azaindoles 1 (1.0 mmol) with amides 2 (1.2 mmol) were performed in a sealed Schlenk tube at 100 °C in dioxane (2 mL) by using Pd(OAc)2 (5 mol %), Xantphos (10 mol %) and base (1.5 mmol). bYields reported are isolated yields. cNR no reaction. dDesulfonation reaction takes place.