1). Why not starting by a Chichibabin reaction?
Then, what could be the product of a reaction of an amine with furan?
2). Do pyridines form arynes?
And if an aryne formed, what could be the product of a reaction with furan?
3). By the way, can you suggest a mechanism of 3-aminopyridine formation from 3-chloropyridine?
PS: Please, decide whether 2-aminopyridine or 3-aminopyridine, because it' not very clear, in your text.