JP6357190B2 - ハロゲン化ピリジン化合物とハロゲン化芳香族化合物のカップリング方法 - Google Patents
ハロゲン化ピリジン化合物とハロゲン化芳香族化合物のカップリング方法 Download PDFInfo
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- JP6357190B2 JP6357190B2 JP2016107878A JP2016107878A JP6357190B2 JP 6357190 B2 JP6357190 B2 JP 6357190B2 JP 2016107878 A JP2016107878 A JP 2016107878A JP 2016107878 A JP2016107878 A JP 2016107878A JP 6357190 B2 JP6357190 B2 JP 6357190B2
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- NBPGPQJFYXNFKN-UHFFFAOYSA-N Cc1cc(-c2nccc(C)c2)ncc1 Chemical compound Cc1cc(-c2nccc(C)c2)ncc1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 description 2
- WIZOYIPSADPMOR-UHFFFAOYSA-N Cc1cc([Ce])ncc1 Chemical compound Cc1cc([Ce])ncc1 WIZOYIPSADPMOR-UHFFFAOYSA-N 0.000 description 2
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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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/127—Preparation from compounds containing pyridine rings
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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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
A.一般式(I)に示すハロゲン化ピリジン化合物においてX1が塩素原子及びR1が水素原子である2-クロロピリジンと、一般式(II)に示すハロゲン化芳香族化合物においてX2が塩素原子、R2が水素原子、及びYが窒素原子である2-クロロピリジンとの組み合わせ、つまり、2-クロロピリジンのホモカップリング。B.一般式(I)に示すハロゲン化ピリジン化合物においてX1が塩素原子及びR1が水素原子である2-クロロピリジンと、一般式(II)に示すハロゲン化芳香族化合物においてX2が臭素原子、R2が水素原子、及びYが炭素原子であるブロモベンゼンとの組み合わせ、つまり、2-クロロピリジンとブロモベンゼンのクロスカップリング。
C.一般式(I)に示すハロゲン化ピリジン化合物においてX1が塩素原子及びR1がメチル基である2-クロロ-4-メチルピリジンと、一般式(II)に示すハロゲン化芳香族化合物においてX2が塩素原子、R2がメチル基、及びYが窒素原子である2-クロロ-4-メチルピリジンとの組み合わせ、つまり、2-クロロ-4-メチルピリジンのホモカップリング。
2-クロロピリジン2mmol、クロロベンゼン1mmolを、THF 1ml中に溶解させ、続いて、0℃にてSDを2mmol添加し3時間反応させた。反応は大気下で行った。結果を図1の実験番号1に示す。その結果、下記の反応式(1)に示す通り、2,2’-ビピリジンが主生成物として得られた。下記反応式(1)には示さないが、6-クロロ-2,2’-ビピリジンが副生成物であった。
2-クロロピリジン2mmol、クロロベンゼン1mmolを、THF 1ml中に溶解させ、続いて、0℃にてSDを1mmol添加し3時間反応させた。反応は大気下で行った。結果を図1の実験番号7に示す。その結果、下記の反応式(2)に示す通り、6-クロロ-2,2’-ビピリジンが主生成物として得られた。下記反応式(2)には示さないが、実施例1の主生成物であった2,2’-ビピリジンが副生成物となった。
2-クロロピリジン1mmolを、THF1ml中に溶解させ、続いて、25℃にてSDを2mmol添加し1時間反応させた。反応は大気下で行った。結果を図1の実験番号11に示す。その結果、下記の反応式(3)に示す通り、4,4’-ビピリジンが主生成物として得られた。下記反応式(3)には示さないが、2,2’-ビピリジンが副生成物であった。
2-クロロピリジン:ブロモベンゼンをモル当量比1:2(1mmol:2mmol)で、THF1ml中に溶解させ、続いて、50℃にて、SDを4mmol添加し3時間反応させた。反応は大気下で行った。結果を図1の実験番号14に示す。その結果、下記の反応式4に示す通り、2-フェニルピリジンが主生成物として得られた。
2-クロロ-4-メチルピリジン2mmolをTHF 1ml中に溶解させ、続いて、50℃にてSD 2mmolを添加し3時間反応させた。反応は大気下で行った。結果を図1の実験番号23に示す。その結果、下記の反応式(5)に示す通り、4,4’-ジメチル-2,2’-ビピリジンのみが生成物として得られた。
2-クロロ-4-メチルピリジン2mmolをTHF 1ml中に溶解させ、続いて、25℃にてSD 2mmolを添加し3時間反応させた。反応は大気下で行った。結果を図1の実験番号25に示す。その結果、下記の反応式(6)に示す通り、4,4’-ジメチル-2,2’-ビピリジンが主生成物として得られた。下記反応式(6)には示さないが、副生成物として、6-クロロ-4,4’-ジメチル-2,2’-ビピリジンも高い比率で生成された。
Claims (7)
- 下記一般式(I)に示すハロゲン化ピリジン化合物と一般式(II)に示すハロゲン化芳香族化合物とを平均粒子径10μm未満のアルカリ金属を分散溶媒に分散させた分散体と反応溶媒中で反応させて、前記ハロゲン化ピリジン化合物と前記ハロゲン化芳香族化合物とのカップリングにより下記一般式(III)に示すピリジン化合物を得る工程、を備えるハロゲン化ピリジン化合物とハロゲン化芳香族化合物のカップリング方法。
- 前記X1及び前記X2が塩素原子であり、前記R1及び前記R2が水素原子であり、前記Yが窒素原子であり、前記X’が水素原子又は塩素原子である請求項1に記載のハロゲン化ピリジン化合物とハロゲン化芳香族化合物のカップリング方法。
- 前記反応溶媒が、クロロベンゼンを含む請求項2に記載のハロゲン化ピリジン化合物とハロゲン化芳香族化合物のカップリング方法。
- 前記X1が塩素原子であり、X2が臭素原子であり、前記R1及び前記R2が水素原子であり、前記Yが炭素原子であり、前記X’が水素原子である請求項1に記載のハロゲン化ピリジン化合物とハロゲン化芳香族化合物のカップリング方法。
- 前記X1及び前記X2が塩素原子であり、前記R1及び前記R2がメチル基であり、前記Yが窒素原子であり、前記X’が水素原子又は塩素原子である請求項1に記載のハロゲン化ピリジン化合物とハロゲン化芳香族化合物のカップリング方法。
- 前記反応溶媒が、テトラヒドロフランである請求項1〜5の何れか一項に記載のハロゲン化ピリジン化合物とハロゲン化芳香族化合物のカップリング方法。
- 前記ピリジン化合物において所定のハロゲン化率を得るため、前記アルカリ金属を含む液体の使用量を調整する請求項1〜6の何れか一項に記載のハロゲン化ピリジン化合物とハロゲン化芳香族化合物のカップリング方法。
Priority Applications (6)
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JP2016107878A JP6357190B2 (ja) | 2016-05-30 | 2016-05-30 | ハロゲン化ピリジン化合物とハロゲン化芳香族化合物のカップリング方法 |
PCT/JP2017/019595 WO2017208970A1 (ja) | 2016-05-30 | 2017-05-25 | ハロゲン化ピリジン化合物とハロゲン化芳香族化合物のカップリング方法 |
CN201780033024.9A CN109219595A (zh) | 2016-05-30 | 2017-05-25 | 卤代吡啶化合物与卤代芳香族化合物的偶联方法 |
US16/305,741 US20200317614A1 (en) | 2016-05-30 | 2017-05-25 | Method for coupling halogenated pyridine compound with halogenated aromatic compound |
EP17806527.2A EP3466927A4 (en) | 2016-05-30 | 2017-05-25 | METHOD OF COUPLING A HALOGENATED PYRIDINE COMPOUND TO A HALOGENATED AROMATIC COMPOUND |
TW106117682A TW201815763A (zh) | 2016-05-30 | 2017-05-26 | 鹵化吡啶化合物與鹵化芳香族化合物之耦合方法 |
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JP2016107878A JP6357190B2 (ja) | 2016-05-30 | 2016-05-30 | ハロゲン化ピリジン化合物とハロゲン化芳香族化合物のカップリング方法 |
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JP6357190B2 true JP6357190B2 (ja) | 2018-07-11 |
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US (1) | US20200317614A1 (ja) |
EP (1) | EP3466927A4 (ja) |
JP (1) | JP6357190B2 (ja) |
CN (1) | CN109219595A (ja) |
TW (1) | TW201815763A (ja) |
WO (1) | WO2017208970A1 (ja) |
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JPWO2019225742A1 (ja) * | 2018-05-24 | 2021-06-24 | 株式会社神鋼環境ソリューション | 有機化合物のカップリング方法 |
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US3227723A (en) * | 1966-01-04 | Process for preparing bipykibyils | ||
US4177349A (en) * | 1978-07-27 | 1979-12-04 | Reilly Tar & Chemical Corporation | Substituted 2,2'-bipyridyl compounds and process for preparing same |
JPH08268929A (ja) * | 1995-03-30 | 1996-10-15 | Nippon Petrochem Co Ltd | アルキル基置換芳香族炭化水素の製造方法 |
EP1905755A1 (en) * | 2006-09-26 | 2008-04-02 | Lonza Ag | Process for the synthesis of 2,2 ,6-tribromobiphenyl |
WO2008059960A1 (fr) * | 2006-11-16 | 2008-05-22 | Jsr Corporation | Procédé de production d'un dérivé 4-pyridinique et intermédiaire pour dérivé 4-pyridinique |
JP2013184947A (ja) * | 2012-03-09 | 2013-09-19 | National Institutes Of Natural Sciences | ビアリール化合物の製造方法 |
WO2017061581A1 (ja) * | 2015-10-08 | 2017-04-13 | 株式会社神鋼環境ソリューション | ビピリジン化合物の合成方法およびピリジン化合物の製造方法 |
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- 2017-05-25 US US16/305,741 patent/US20200317614A1/en not_active Abandoned
- 2017-05-25 CN CN201780033024.9A patent/CN109219595A/zh active Pending
- 2017-05-25 WO PCT/JP2017/019595 patent/WO2017208970A1/ja unknown
- 2017-05-25 EP EP17806527.2A patent/EP3466927A4/en not_active Withdrawn
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Publication number | Publication date |
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JP2017214306A (ja) | 2017-12-07 |
CN109219595A (zh) | 2019-01-15 |
US20200317614A1 (en) | 2020-10-08 |
EP3466927A1 (en) | 2019-04-10 |
TW201815763A (zh) | 2018-05-01 |
WO2017208970A1 (ja) | 2017-12-07 |
EP3466927A4 (en) | 2019-11-27 |
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