A novel approach to 3-methylindoles by a Heck/cyclization/isomerization process.
A novel synthesis of 3-methylindoles from chlorotriflates through a Heck reaction, carbamate/aryl chloride coupling, and isomerization sequence is presented. The three-step sequence is highly efficient and general, enabling the regiocontrolled synthesis of substituted indoles in short order.
Baxter
Carl A
CA
Department of Process Research, Merck Sharp and Dohme Research Laboratories, Hertford Road, Hoddesdon, Hertfordshire, EN11 9BU, United Kingdom. carl_baxter2@merck.com
Cleator
Ed
E
Alam
Mahbub
M
Davies
Antony J
AJ
Goodyear
Adrian
A
O'Hagan
Michael
M
D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D012862:Skatole / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D006843:Hydrocarbons, Chlorinated; D008698:Mesylates; D012862:Skatole