[Rookie_OC_Lover]

my final(not final really) product is going to be the attached image .

I wouldn't care if the blue marked hydrogen gets replaced by the following groups:
CN, OH, COOH, SH

the red marked H is what i emphasize to be intact.

Tnx

[Archer]

PBr₃ will be selective towards the alcohol rather than the aromatic carbons.

Having said that there may be competition with the C3 if the reaction with PBr₃ is S_N1 rather than S_N2.

[Rookie_OC_Lover]

Having said that there may be competition with the C3 if the reaction with PBr₃ is S_N1 rather than S_N2.

Would you please explain why do you think Sn1 should be considered to happen ?
OH group in indole-3-carbinol isn't a good leaving group. (unless we force it)
or maybe i'm not taking some stuff into account 

[Babcock_Hall]

Can you think of a route that involves reduction?  I am not saying that this would better than the route involving oxidation.

Reducing what ?
like turning 3-Bromo-1-iodo-Propane to the desired aldehyde ?

I was thinking of reducing an acid to the aldehyde.  We had a nice discussion about this transformation on a thread here a few weeks ago.  I can see that it might take two steps*.  Why don't you write it out?
*or three.

[Rookie_OC_Lover]

We had a nice discussion about this transformation on a thread here a few weeks ago.

can you give me that forum name or address.
Tnx agn

[Babcock_Hall]

We had a nice discussion about this transformation on a thread here a few weeks ago.

can you give me that forum name or address.
Tnx agn

By typing "aldehyde" into the search function here, I found:  http://www.chemicalforums.com/index.php?topic=67874.0

[Archer]

Having said that there may be competition with the C3 if the reaction with PBr₃ is S_N1 rather than S_N2.

Would you please explain why do you think Sn1 should be considered to happen ?
OH group in indole-3-carbinol isn't a good leaving group. (unless we force it)
or maybe i'm not taking some stuff into account 

If the hydroxyl is protonated then the resonance structure of the carbocation would be relatively stable. although thinking about it the attack would be on C2 rather than C3. I am not saying that it would happen just that some might.

You see the thing with synthesis is that you need to experiment and find which route gives the highest yield or the fewest side reactions.

Best of luck whichever route you choose.

[TwistedConf]

You see the thing with synthesis is that you need to experiment and find which route gives the highest yield or the fewest side reactions.

True, but a lit search is in order here. The transformations being discussed (formation and bromination of that indole C-3 hydroxymethyl) are known and have already been reported.

It all works but you'll have to protect the nitrogen, of course.

[Rookie_OC_Lover]

The transformations being discussed (formation and bromination of that indole C-3 hydroxymethyl) are known and have already been reported.

It all works but you'll have to protect the nitrogen, of course.

is it reported ? where ? any papers on it ?

thanks a lot friends.