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Indeed, we can see here that phenol itself is not sufficiently acidic to react with Na₂CO₃: Phenol Preparing, Reactions, Physical Properties
Phenol will be released from sodium phenolate by carbon dioxide/carbonic acid, since carbonic acid (pK₁=6.77) is a stronger acid than phenol (pKa=10.0).

I would strongly suspect that indol-5-ol is even less acidic than phenol itself, making the situation for bufo freebase even more favorable.

[QUOTE="downwardsfromzero, post: 3865341, member: 1025"] Indeed, we can see here that phenol itself is not sufficiently acidic to react with Na₂CO₃: [URL="https://www.chemistryscl.com/advancedlevel/organic/phenol/main.html#Phenol%20and%20aqueous%20NaOH%20reaction"]Phenol Preparing, Reactions, Physical Properties[/URL] Phenol will be released from sodium phenolate by carbon dioxide/carbonic acid, since carbonic acid (pK₁=6.77) is a stronger acid than phenol (pKa=10.0). I would strongly suspect that indol-5-ol is even less acidic than phenol itself, making the situation for bufo freebase even more favorable. [/QUOTE]