Palladium catalyzed indolization of 2-bromo or chloroanilines

Details Palladium catalyzed indolization of 2-bromo or chloroanilines Palladium catalyzed indolization of 2-bromo or chloroanilines

2006-10-24

2006-10-24

Saeed, Kamal A. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S406000, C548S407000, C548S503000, C546S277400, C546S015000

Reexamination Certificate

active

07126009

ABSTRACT:
The present invention provides a method for making substituted indole compounds of general formula III comprising the step of:(a) reacting a 2-bromoaniline or 2-chloroaniline of general formula (I)(I)wherein: X, R and R1are defined hereinwith a substituted acetylene of formula (II)wherein R2and R3are defined herein in the presence of a palladium catalyst, a ligand, and a base in a solvent at a suitable temperature to give a compound of formula (III);

REFERENCES:
R.C. Larock, et al. “Synthesis of 2,3-Disubstituted Indoles via Palladium-Catalyzed Annulation of Internal Alkynes”, Journal of Organic Chemistry, 1998, vol. 63, pp. 7652-7662 XP 002375382.
F. Maassarani, et al. “Controlled Synthesis of Heterocyclic Compounds through Ring Enlargement by Alkyne Insertions into the PD-C Bonds of Cyclopalladated Amines Followed by Subsequent Ring Closure”, Organometallics, 1987, vol. 6, pp. 2029-2043 XP-002375383.
F. Maassarani, et al. “Stepwise Insertion of One, Two, and Three Alkyne Molecules into the Pd-C Bond of a Six-Membered Palladocycle. One-Pot Synthesis of Spirocyclic Compounds”, Organometallics, 1987, vol. 6, pp. 2043-2053 XP-002375384.
F. Maassarani, et al., “Selective hetero- and carbo-cycle synthesis via masked cyclopalladated secondary amine and ketone functions”, J. Organometallic Chemistry, vol. 466, 1994, pp. 265-271 XP-002375385.
Database Zregistry [Online] Dec. 12, 1987, XP002377297 retrieved from STN RN: 111783-46-1 ABSTRACT.
Database Zregistry [Online] Nov. 16, 1984, XP002377298, retrieved from STN RN: 2486-71-7 ABSTRACT.
Database Zregistry [Online] Nov. 16, 1984, XP002377299, retrieved from STN RN: 95-74-9 ABSTRACT.
M. Shen, et al. “The First Regioselective Palladium-Catalyzed Indolization of 2-Bromo- or 2-Chloroanillnes with Internal Alkynes: A New Approach to 2,3-Disubstituted Indoles”, Organic Letters, vol. 6, No. 22, pp. 4129-4132 XP-002375386.

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