Hi Respected RG member,
I have a question. How can I synthesize 4-bromoindole and 4-methylindole? Thanks!
The question is too general, from which starting materials do you want them, how much is your budget which will control the number of steps, etc
So for 4-bromoindole, you can synthesis it from 4-Bromo-1-[(trifluoromethyl)sulfonyl]-1H-indole or from Methyl 4-bromo-1H-indole-3-carboxylate
Please check the below papers FYR:
Pd(II)-Catalyzed Amination of C-H Bonds Using Single-Electron or Two-electron Oxidants.
J. AM. CHEM. SOC. 2009, 131, 10806–10807
A New Synthesis of Lysergic Acid
org. Lett. 2004, 6, 1, 3–5
For 4-methylindole you can synthesize it by Dehalogenation from 7-Bromo-4-methyl-1H-indole which is commercially available
The Synthesis of 4-bromo indole can be via Batcho-Leimgruber indole synthesis as illustrated below. Find the article through this link: Moyer, M. P., Shiurba, J. F., & Rapoport, H. (1986). Metal-halogen exchange of bromoindoles. A route to substituted indoles. The Journal of Organic Chemistry, 51(26), 5106-5110.
Similarly, the synthesis of 4-methyl indole can be achieved using Dobbs modification to the Bartoli indole synthesis as illustrated below. Find more information from this link: https://en.wikipedia.org/wiki/Bartoli_indole_synthesis
Dear Kumar,
Please share your email address for corresponding. I am going to send you information there.
Best regards,
Yordan
Yordan Stremski thank you for your response
My corresponding email- [email protected]
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