Table 3.

Synthesis of 2-aminopyridines from 2,3-pyridyne and various amines^a

Entry	Aryne precursor	Amine	Product	Yieldb (%)
1		PhMeNH 2a		65
2		PhNH2 2b		58
3				57
4				64
5				61
6				47
7				46
8				60
9		Bn2NH 2i		57
10				36

^aAll reactions were carried out on a 0.25 mmol scale with 2 equiv of CsF at room temperature. A solution of 1 in 4 mL of MeCN (solution A) and a solution of 2 and CsF in 4 mL of MeCN (solution B) were prepared separately. Solution A was slowly added to solution B with a syringe pump over 8 h, the resulting solution was stirred for an additional 16 h.

^bIsolated yield.