CA2764241C - Disubstituted-aminodifluorosulfinium salts, process for preparing same and method of use as deoxofluorination reagents - Google Patents

Disubstituted-aminodifluorosulfinium salts, process for preparing same and method of use as deoxofluorination reagents Download PDF

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Publication number
CA2764241C
CA2764241C CA2764241A CA2764241A CA2764241C CA 2764241 C CA2764241 C CA 2764241C CA 2764241 A CA2764241 A CA 2764241A CA 2764241 A CA2764241 A CA 2764241A CA 2764241 C CA2764241 C CA 2764241C
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Prior art keywords
tetrafluoroborate
mmol
disubstituted
dichloromethane
nmr
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CA2764241A
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English (en)
French (fr)
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CA2764241A1 (en
Inventor
Michel Couturier
Alexandre L'heureux
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Omegachem Inc
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Omegachem Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/76—Nitrogen atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
    • C07C381/10—Compounds containing sulfur atoms doubly-bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B39/00—Halogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/16—Preparation of halogenated hydrocarbons by replacement by halogens of hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
    • C07C17/18—Preparation of halogenated hydrocarbons by replacement by halogens of oxygen atoms of carbonyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
    • C07D207/48—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
    • C07D295/26—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Saccharide Compounds (AREA)
CA2764241A 2009-06-19 2010-06-18 Disubstituted-aminodifluorosulfinium salts, process for preparing same and method of use as deoxofluorination reagents Active CA2764241C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US21859209P 2009-06-19 2009-06-19
US61/218,592 2009-06-19
US24770309P 2009-10-01 2009-10-01
US61/247,703 2009-10-01
PCT/CA2010/000959 WO2010145037A1 (en) 2009-06-19 2010-06-18 Disubstituted-aminodifluorosulfinium salts, process for preparing same and method of use as deoxofluorination reagents

Publications (2)

Publication Number Publication Date
CA2764241A1 CA2764241A1 (en) 2010-12-23
CA2764241C true CA2764241C (en) 2016-03-08

Family

ID=43355653

Family Applications (1)

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CA2764241A Active CA2764241C (en) 2009-06-19 2010-06-18 Disubstituted-aminodifluorosulfinium salts, process for preparing same and method of use as deoxofluorination reagents

Country Status (7)

Country Link
US (1) US8680332B2 (enExample)
EP (1) EP2443087B1 (enExample)
JP (1) JP2012530075A (enExample)
KR (1) KR20120046718A (enExample)
CN (1) CN102482209B (enExample)
CA (1) CA2764241C (enExample)
WO (1) WO2010145037A1 (enExample)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2764241C (en) 2009-06-19 2016-03-08 Omegachem Inc. Disubstituted-aminodifluorosulfinium salts, process for preparing same and method of use as deoxofluorination reagents
CN107074899A (zh) * 2014-10-31 2017-08-18 桑多斯股份公司 改进的氟化工艺
EP4610245A1 (en) * 2022-10-25 2025-09-03 Agc Inc. Fluorine-containing compound production method
CN117447299A (zh) * 2023-10-31 2024-01-26 凯莱英医药化学（阜新）技术有限公司 偕二氟代化合物的合成方法
CN119654036B (zh) * 2024-12-13 2026-03-03 福州大学 一种具有均匀吸收层组分梯度的硫硒化锑太阳电池的制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5389708A (en) * 1992-01-31 1995-02-14 Mitsui Toatsu Chemicals, Inc. Sulfur-containing acid phosphoric ester internal release agent
US6080886A (en) * 1997-09-29 2000-06-27 Air Products And Chemicals, Inc. Fluorination with aminosulfur trifluorides
US6096922A (en) * 1999-11-01 2000-08-01 Air Products And Chemicals, Inc. Process for the synthesis of dialkyl, diaryl, and arylalkyl aminosulfur trifluorides
US6462191B1 (en) * 2000-07-13 2002-10-08 Air Products And Chemicals, Inc. Synthesis of 2-deoxy-2-fluoro-arabinose derivatives
JP4577478B2 (ja) * 2002-12-04 2010-11-10 三菱瓦斯化学株式会社 糖質のフッ素化方法
CN100338012C (zh) * 2005-11-07 2007-09-19 上海泰卓科技有限公司 一种含氟酰氟类化合物的处理方法
EP1892231A1 (en) * 2006-08-21 2008-02-27 Bayer Schering Pharma Aktiengesellschaft A large scale method for the deoxofluorination of ketones
CA2764241C (en) 2009-06-19 2016-03-08 Omegachem Inc. Disubstituted-aminodifluorosulfinium salts, process for preparing same and method of use as deoxofluorination reagents

Also Published As

Publication number Publication date
EP2443087A4 (en) 2012-12-05
JP2012530075A (ja) 2012-11-29
US8680332B2 (en) 2014-03-25
CA2764241A1 (en) 2010-12-23
US20120108801A1 (en) 2012-05-03
CN102482209B (zh) 2014-08-20
WO2010145037A1 (en) 2010-12-23
CN102482209A (zh) 2012-05-30
EP2443087A1 (en) 2012-04-25
EP2443087B1 (en) 2016-06-08
KR20120046718A (ko) 2012-05-10

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