[clarkstill]

As Babcock_Hall said, you could try DCC/DMAP (Steglich Esterification), which should avoid any difficulties involved with forming the acyl chlorides. It is also carried out under basic conditions, so you'd avoid any issues associated with protonation of your pyridines. I'd go for that.

[OrganicDan96]

I would definitely go for a coupling such as DCC/DMAP. acid chloride esterification are always a bit messy.

[wildfyr]

I would be concerned about getting dicycolhexylurea byproduct out with such a polar product. If you go this way, recrystallization in MeCN is the best trick for removing DCU.

[clarkstill]

Or use EDC

[clarkstill]

Or use EDC

Although now I think about it, the acid wash might pull out your BIPY product too