prepared via ethylamine loading by reductive amination five different synthesis methods a e were tested method a reduction with nabh 4 in thf etoh 4 1 1 two g of 3 aldehyde indolylmethyl resin imr cho sub 1 2 mmole g total sub 2 4 mmole or 0 0024 mole was swelled in 20 ml of tetrahydrofuran thf by stirring for approximately 10 minutes the resin was filtered and then mixed with 40 ml of thf 0 8 ml ethylamine 12 mmole 5 eq was added and the mixture was stirred overnight approximately 20 hours nabh 4 0 91 g 24 mmole 10 eq and etoh 10 ml were added and the mixture was stirred for 6 7 hours approximately 20 ml of water was added the mixture was stirred for 10 15 minutes and then filtered the resin was washed with water meoh dmf and meoh 2 3 times each and then dried the ethylamine loaded resin was colorless and weighed 2 11 g a sample 100 mg of the ethylamine loaded resin was reacted with fmoc cl in dcm containing 10 diisopropylethylamine diea for 2 3 hours it was filtered and washed with dcm dmf dcm and meoh and then dried to yield the fmoc eam imr substitution was found to be 0 79 mmole g using the dbu method it was reacted again with fmoc cl to reconfirm the reaction substitution was found to be 0 85 mmole g.