[Altered State]

How would you suggest a mechanism fot the reaction that appears in the top of the picture?



I think that it would be very very similar to Fischer indol synthesis, but in this case we have a pyridine ring and a Cl attached to it.
My suggest is in the picture, and I post it here because I don't see if the last step I've drawn is correct. Could it be that electron density pushes Cl- out of the molecule while bonding the pyridine ring to the cyclohexyl ring in that [3, 3]reaction? I'm not so sure of it.

I did not draw the rest of the mechanism beacuse it would be exactly the same than fischer's.

Another think were I find that could be a problem is that it's said to be a base catalyzed reaction, while FIsher's Indols synthesis occurs in acidic media.

[TwistedConf]

All your intermediates have three nitrogens. The starting materials have two.

[Altered State]

All your intermediates have three nitrogens. The starting materials have two.

Woops. Don't know what was wrong with my mind last night 
Got it now, thanks