How to convert indole to tryptamine ?

1. POCl3-DMF to make the indole aldehyde,
2.nitromethane to make unsaturated nitro indole.
3. LAH reduction to give you tryptamine.

to save one step, step 1 and 2 can be made into one step:
TFA, (CH3)2N-CH=CH-NO2, DCM to make the unsaturated nitro indole.

to increase the functional group compatibility of this sequence,
the LAH reduction step can be replaced by a 2 step sequence:
1. NaBH4/SiO2 reduction to take off the double bond.
2. Fe/AcOH reduction to convert the nitro group to amine.