Table 1.

^a

S. No	solvent(s)b v/v	saltc	T (°C) and time (h)	% yieldd
1	AcOH/H2O (1:5)	NaOAc	RT, 24 (h)	30% total yield
2	AcOH/H2O/MeOH (1:5:1)	NaOAc	RT, 24 (h)	23% total yield
3	AcOH	NaOAc	RT, 24 (h)	70% C3-prenylation, 6% C2-prenylation
4	EtOAc/MeOH (1:1)	NaOAc	RT, 24 (h)	69% N-prenylation
5	ACN/MeOH (1:1)	NaOAc	RT, 24 (h)	65% N-prenylation
6	MeOH		RT, 24 (h)	70% N-prenylation
7	DMSO		50 °C, 5 (h)	no reaction

^aReaction conditions: l-Trp-OMe (100 mg, 0.458 mmol, 1.0 equiv), prenyl bromide (10) (105 μL, 0.92 mmol, 2 equiv) in various solvents.

^bReaction performed in 0.1 M solvent(s).

^c2.0 equiv of salt added.

^dProducts isolated after purification by column chromatography: C3/C2/N-prenylation determined by NMR analyses.