Question

How does the mechanism for this intermediate even occur? How does the amine replace the Vinyl Ether?

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This is a "Friedlander−Pfitzinger" reaction, turning the Isatin to a Quinidine. For the Amine to replace the Vinyl Ether on (17), that Vinyl Ether would need to be Hydrolyzed. That, however, only happens in strong acids, while this is basic. By what mechanism does the amine replace the vinyl ether here if the conditions are basic?

Paper Source: http://dx.doi.org/10.1021/jacs.6b04339


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