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WO2018231627A1 - 2,5-dibromopyridine et procédés de préparation - Google Patents

2,5-dibromopyridine et procédés de préparation Download PDF

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Publication number
WO2018231627A1
WO2018231627A1 PCT/US2018/036446 US2018036446W WO2018231627A1 WO 2018231627 A1 WO2018231627 A1 WO 2018231627A1 US 2018036446 W US2018036446 W US 2018036446W WO 2018231627 A1 WO2018231627 A1 WO 2018231627A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
contacting
preparation
dibromopyridine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2018/036446
Other languages
English (en)
Inventor
Qiang Yang
Kaitlyn Gray
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mycovia Pharmaceuticals Inc
Original Assignee
Viamet Pharmaceuticals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Viamet Pharmaceuticals Inc filed Critical Viamet Pharmaceuticals Inc
Publication of WO2018231627A1 publication Critical patent/WO2018231627A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C07D213/61—Halogen atoms or nitro radicals

Definitions

  • the compound of Formula II may be prepared by contacting compound of Formula III with a brominating reagent.
  • hydroxyl refers to an -OH substituent.
  • halogen refers to one or more halogen atoms, defined as F, CI, Br, and I.
  • organometallic refers to an organic compound containing a metal, especially a compound in which a metal atom is bonded directly to a carbon atom.
  • Room temperature is defined herein as about 20 °C to about 25 °C.
  • Method B To 5-bromo-2-hydroxypyridine (1 g, 5.75 mmol) was added phosphorus tribromide (2.71 mL, 28.7 mmol) making a white slurry that was heated at 140 °C for 30 h. The reaction was allowed to cool to room temperature and was poured into water (30 mL). The mixture was extracted with ethyl acetate (100 mL). The aqueous layer was basified with 2 N NaOH and extracted with ethyl acetate (50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated giving 2,5-dibromopyridine (770 mg, 2.93 mmol, 51%) as a yellow solid. Analytical data matched the data shown in Method A. The process exemplified in Example 1 may be conducted with phosphorus oxybromide, phosphorous tribromide, phosphorous pentabromide, or mixtures thereof.
  • Solvents for use in this process may include aprotic solvents selected from
  • the process may also be conducted with no solvent.
  • the process may be conducted at a temperature of about 20 °C to about 180 °C.
  • Example 2 The process exemplified in Example 2 may be conducted with one or more brominating reagents selected from the group including N-bromosuccinimide, 1,3-dibromo- 5,5-dimethylhydantoin, and bromine.
  • one or more brominating reagents selected from the group including N-bromosuccinimide, 1,3-dibromo- 5,5-dimethylhydantoin, and bromine.
  • Example 2 The process exemplified in Example 2 may be conducted in a solvent such as acetic acid.
  • Example 2 The process exemplified in Example 2 may be conducted at a temperature of about 25 C to about 125 °C.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de préparation de 2,5-dibromopyridine.
PCT/US2018/036446 2017-06-12 2018-06-07 2,5-dibromopyridine et procédés de préparation Ceased WO2018231627A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201762518097P 2017-06-12 2017-06-12
US62/518,097 2017-06-12

Publications (1)

Publication Number Publication Date
WO2018231627A1 true WO2018231627A1 (fr) 2018-12-20

Family

ID=64660649

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2018/036446 Ceased WO2018231627A1 (fr) 2017-06-12 2018-06-07 2,5-dibromopyridine et procédés de préparation

Country Status (3)

Country Link
AR (1) AR112138A1 (fr)
UY (1) UY37763A (fr)
WO (1) WO2018231627A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112679420A (zh) * 2020-12-27 2021-04-20 甘肃瀚聚药业有限公司 一种2,5-二溴吡啶的制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040186104A1 (en) * 2001-05-04 2004-09-23 Magnus Johansson Novel pyridinone and related heterocyclic derivatives

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040186104A1 (en) * 2001-05-04 2004-09-23 Magnus Johansson Novel pyridinone and related heterocyclic derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DAMONT, A ET AL.: "Synthesis of 6-[18F] fluoro-PBR28, a novel radiotracer for imaging the TSPO 18 kDa with PET", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 21, no. 16, 2011, pages 4819 - 4822, XP028247194 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112679420A (zh) * 2020-12-27 2021-04-20 甘肃瀚聚药业有限公司 一种2,5-二溴吡啶的制备方法
CN112679420B (zh) * 2020-12-27 2023-05-12 甘肃瀚聚药业有限公司 一种2,5-二溴吡啶的制备方法

Also Published As

Publication number Publication date
AR112138A1 (es) 2019-09-25
UY37763A (es) 2019-01-31

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