Nitrobenzene → 7-fluoro-5H-indeno[1,2-b]pyridin 5,5-thiazolidine

HRID 1607422

Reaction equation

HRID 1607422 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=CC=1)([O-])=O.[F:10][C:11]1[CH:12]=[C:13]2[C:21](=[CH:22][CH:23]=1)[C:16]1=[N:17][CH:18]=[CH:19][CH:20]=[C:15]1[CH2:14]2>C1(C)C(C)=CC=CC=1.[Pd]>[F:10][C:11]1[CH:12]=[C:13]2[C:21](=[CH:22][CH:23]=1)[C:16]1=[N:17][CH:18]=[CH:19][CH:20]=[C:15]1[CH2:14]2.[CH2:4]1[NH:1][CH2:7][CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 7416NitrobenzeneHCID 136013787-fluoro-5H-indeno[1,2-b]pyridine

Product 1

HCID 867402727-fluoro-5H-indeno[1,2-b]pyridin 5,5-thiazolidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

The tetrahydroimine product is aromatized in xylene and nitrobenzene and 10% palladium on charcoal according to Parcell and Hauch, ibid. The resulting product, e.g., 7-fluoro-5H-indeno[1,2-b]pyridine (which may be further derivatized according to Metho V) is derivatized according to Methods II to IV to yield the corresponding spiro-derivatives such as spiro-(7-fluoro-5H-indeno[1,2-b]pyridin-5,5-thiazolidine)-2',4'-dione; spiro-(7-fluoro-5H-inden[1,2-b]pyridin-5,5'-(oxazolidine)-2',4'-dione and spiro-(7-fluoro-5H-indeno[1,2-b]pyridin-5,3'-suiccinimide. Oxidation (Method VII) of 5H-indeno[1,2-b]pyridine or its derivatives according to the method of Sprinzak, J. Amer. Chem. Soc., 80, 5449 (1958) yields the corresponding 5-one or ketone derivative, which may be further derivatized according to Method V. When reacted in accordance with Method I, the ketone will yield a spiro-hydantoin derivative such as spiro-(7-fluoro-5H-indeno[1,2-b]pyridin-5,4'-imidazoline)-2',5'-dione. Any of the aforementioned spiro derivatives may be further derivatized, e.g., nitrated, in accordance with Method VI. See Examples XVIII, XI and XII.

Sources & evidence

ORD record
ord-490e0560668646ce92b0e90afe2bb292
Source dataset
uspto-grants-1989_09
Patent number
US04864028

Linked notes

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