Organic compounds -- part of the class 532-570 series – Organic compounds – Halogen containing
Reexamination Certificate
2008-07-29
2008-07-29
Witherspoon, Sikarl A (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Halogen containing
C556S454000, C548S253000, C546S016000, C546S124000, C564S293000
Reexamination Certificate
active
07405332
ABSTRACT:
The invention provides a process for preparation of a fluorohaloalkane, preferably an [18F]fluorohaloalkane of formula (I) wherein X is halo and n is an integer of from 1 to 6; which comprises: reaction of the corresponding organosilicon compound of formula (II): wherein n is as defined for the compound of formula (I); and R′, R″, and R′″ are independently selected from C1-6alkyl and C1-6haloalkyl; and R″ may alternatively be the group: with a compound of formula (III): wherein X is as defined for the compound of formula (I) and Y is halo. Intermediates having use in such processes are also claimed.
REFERENCES:
patent: 5210247 (1993-05-01), Haberle et al.
patent: 5536732 (1996-07-01), Lesur et al.
patent: 02290885 (1990-11-01), None
Oh et al. Comparison of [18F] Fluoropropylating Agents for 18F-Radiolabeling of Amines. Bulletin of the Korean Chemical Society, 2000, vol. 21 (11), pp. 1162-1164.
Comagic et al. Efficient Synthesis of 2-bromo-1-[18F] fluoroethane and its application in the automated preparation of 18F-fluoroethylated compounds. Applied Radiation and Isotopes, 2002, vol. 56, pp. 847-851.
Zhang, M-R, et.al., “Development of an Automated System for Synthesizing F-labeled Compounds Using [F]fluoroethyl Bromide as a Synthetic Precursor” Applied Radiation and Isotopes, Pergaon Press Ltd., Exeter, GB, vol. 57, No. 3, Sep. 2002, pp. 335-342.
E.S. Alexander, et.al., Polyfluoroalkyl Compounds of Silicon. Part IX. Silanes containing the Bis(trifluoromethyl)amino-group >> J. Chem. Soc. A., 1970, pp. 2285-2291.
Dietmar Seyferth, et.al., “Halomethyl-metal compounds. Phenyl(fluorodibromomethyl)mercury, a fluorobromacarben precursor” J. Organomet. Chem., vol. 51, 1973, pp. 77-87.
Edmund K.S. Liu, et.al., Fluorinationo f dimethylmercury, tetramethylsilane and tetramethylgermanium J. Organomet., Chem., 1978, pp. 167-182.
Roger L. Scholl, et al., “Silicon-29 Chemical shifts of Organosilicon Compounds” J. Am. Checm. Soc., vol. 94, No. 18, 1972, pp. 6376-6385.
D. Cooper, et.al., “Polyfluoroalkyl Compounds of Silicon. VIII Reactions of Silanes with Vinyl Fluoride and with 1-Chloro-2-fluoroethylene” J. Chem. Soc. A., vol. 196, 1967, pp. 2098-2103.
J. Vcelak, et.al., The Exchange of Fluorine in (gamma-fluoropropyl)trialkylsilanes and n-heypyl fluoride for halogens of grignard reagents Collection Czechoslov. Chem. Commun., vol. 41, 1976, pp. 131-139.
J. Vcelak, et.al, “19F-NMR spectra of (Fluoroalkyl)-substituted Silates” Collection Czechslov., Chem. Commun., vol. 41, 1976, pp. 386-390.
V.B. Puchnarevic et.al., Synthesis of gamma-fluoropropyl Substituted Silanes, Collection Czechoslov., Chem. Commun., vol. 39, 1974 pp. 2616-2620.
CAPLUS Abstract Accession No. 1999:304473 & Journal of Organic Chemistry vol. 64, No. 12, 1999, Ung chan Yoon, et.al, “A Solvent Effect that Influences the Preparative Utility of N-(silyalkyl)phthalimide and N-(silylalkyl)maleimide photochemistry”, pp. 4411-4418 (see abstract).
CAPLUS Abstract Accession No. 1998: 352139 & JP 1014758 A2 (Fujisawa Pharmaceutical Co. Ltd., Japan) Feb. 6, 1998 (see abstract).
CAPLUS Abstract Accession No. 1996:446320 & JP 08092258A2 (Mitsui Petrochemical Ind, Japan) Sep. 4, 1996 (see abstract).
CAPLUS Abstract Accession No. 1989 :534246 & Journal of the Chemical society, Chemical Communications vol. 17, 1988, Steven L. Jones, et.al., “Protophilic versus silicophilic reactions in β-substituted silanes”, pp. 1153-1154 (see abstract).
CAPLUS Abstract Accession No. 1994:30806 & Organometallics vol. 12, No. 12, 1993, Hans Buerger and Peter Moritz, “Novel (fluoromethyl)silicon derivatives from (fluorodibromomethyl) silane precursors”, pp. 4930-4939 (see abstract).
CAPLUS Abstract Accession No. 1980:494362 & Collection of Czechoslovak Chemical Communications vol. 45, No. 3, 1980, Marie Jakoubkova, et.al., Organosilicon compounds. CLXVII. Carbon-fluorine bond stretching frequency (v(C-F)) in some organosilicon compounds, pp. 854-860 (see abstract).
CAPLUS Abstract Accession No. 1977:42771 & Collection of Czechoslovak Chemical Communications vol. 41, No. 9, 1976,J Vcelak, et.al., “Organisilicon compounds. CXLII. The reactivity of fluorine in (ω-fluoroalkyl)-substituted silanes”, pp. 2708-2713.
International Search Report for PCT/GB03/04026 dated Mar. 2004.
Search Report for GB 0222426.9 dated Mar. 2003.
Search Report for GB 0222426.9 dated Aug. 2003.
International Preliminary Examination Report for PCT/GB03/04026 dated Jan. 2005.
Brady Frank
Luthra Sajinder
Zhao Yongjun
Hammersmith Imanet Ltd.
Witherspoon Sikarl A
LandOfFree
Chemical process does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Chemical process, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Chemical process will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2762881