CN1107054C - 2,4'-联吡啶基衍生物的制备方法和分离方法及其应用 - Google Patents
2,4'-联吡啶基衍生物的制备方法和分离方法及其应用 Download PDFInfo
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- CN1107054C CN1107054C CN98800941A CN98800941A CN1107054C CN 1107054 C CN1107054 C CN 1107054C CN 98800941 A CN98800941 A CN 98800941A CN 98800941 A CN98800941 A CN 98800941A CN 1107054 C CN1107054 C CN 1107054C
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- bipyridyl
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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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
实施例1 | 实施例2 | 实施例3 | 实施例4 | ||
催化剂的制备 | |||||
镍配合物催化剂(30mol%) | NiBr2(PPh3)21.11g | NiBr2(PPh3)21.11g | NiCl2(PPh3)2981mg | NiCl2(PPh3)2981mg | |
锌(1.5当量) | 490mg | 490mg | 490mg | 490mg | |
Et4NI(1当量) | 1.28g | 1.28g | 1.28g | 1.28g | |
溶剂 | THF | THF | THF | THF | |
反应时间 | 30min. | 30min. | 30min. | 30min. | |
原料的制备 | |||||
2-氯吡啶 | 4mmol | 3mmol | 4mmol | 2.5mmol | |
盐酸4-氯吡啶 | 1mmol | 2mmol | 1mmol | 2.5mmol | |
三乙胺 | 1mmol | 2mmol | 1mmol | 2.5mmol | |
溶剂 | DMF | DMF | DMF | DMF | |
反应时间 | 1hr | 1hr | 1hr | 1hr | |
反应 | |||||
反应温度 | 50℃ | 50℃ | 50℃ | 50℃ | |
反应时间 | 16hr | 16hr | 16hr | 16hr | |
结果 | |||||
2,2’-联吡啶基收率% | 73mg(23%) | 45mg(19%) | 88mg(28%) | 72mg(18%) | |
2,4’-联吡啶基收率% | 99mg63% | 193mg61% | 132mg84% | 198mg51% | |
4,4’-联吡啶基收率% | -0% | 57mg(36%) | -0% | 57mg15% |
实施例5 | 实施例6 | 实施例7 | ||
催化剂的制备 | ||||
镍配合物催化剂(30mol%) | NiCl2(PPh3)2981mg | NiCl2(PPh3)2981g | NiCl2(PPh3)2981mg | |
锌 | 490mg | 490mg | 490mg | |
Et4NI | - | 1.28g | 1.28g | |
溶剂 | DMF | THF+DMF(10ml+5ml) | 丙酮 | |
反应时间 | 30min. | 30min. | 30min. | |
原料的制备 | ||||
2-氯吡啶 | 2.5mmol | 2.5mmol | 2.5mmol | |
盐酸4-氯吡啶 | 2.5mmol | 2.5mmol | 2.5mmol | |
三乙胺 | 2.5mmol | 2.5mmol | 2.5mmol | |
溶剂 | DMF | 直接加入 | 丙酮 | |
反应时间 | 1hr | 1hr | ||
反应 | ||||
反应温度 | 50℃ | 50℃ | 50℃ | |
反应时间 | 16hr | 16hr | 16hr | |
结果 | ||||
2,2’-联吡啶基收率% | 43mg11% | 28mg7% | 65mg17% | |
2,4’-联吡啶基收率% | 161mg41% | 163mg42% | 113mg29% | |
4,4’-联吡啶基收率% | 81mg21% | 103mg26% | 24mg6% |
实施例8 | 实施例9 | ||
催化剂的制备 | |||
镍配合物催化剂(10mol%) | NiCl2(PPh3)2327mg | NiCl2(PPh3)2327mg | |
锌 | 157mg | 490mg | |
Et4NI | - | 427mg | |
溶剂 | DMF | THF | |
反应时间 | 30min. | 30min. | |
原料的制备 | |||
2-氯吡啶 | 2.5mmol | 2.5mmol | |
盐酸4-氯吡啶 | 2.5mmol | 2.5mmol | |
三乙胺 | 2.5mmol | 2.5mmol | |
溶剂 | DMF | THF | |
反应时间 | 1hr | 1hr | |
反应 | |||
反应温度 | 50℃ | 50℃ | |
反应时间 | 16hr | 16hr | |
结果 | |||
2,2’-联吡啶基收率% | 50mg13% | 79mg*20%* | |
2,4’-联吡啶基收率% | 94mg24% | 129mg33% | |
4,4’-联吡啶基收率% | 70mg18% | 103mg26% |
实施例11 | 实施例12 | 实施例13 | ||
催化剂的制备 | ||||
镍配合物催化剂(30mol%) | NiCl2(PPh3)2981mg | NiCl2(PPh3)2981mg | NiCl2(PPh3)2981mg | |
锌 | 490mg | 490mg | 490mg | |
Et4NI | 1.28g | 1.28g | 1.28g | |
溶剂 | THF | 甲苯 | 甲苯 | |
反应时间 | 30min. | 30min. | 30min. | |
原料的制备 | ||||
2-氯吡啶 | 2.5mmol | 2.5mmol | 2.5mmol | |
盐酸4-氯吡啶 | 2.5mmol | 2.5mmol | 2.5mmol | |
三乙胺 | 2.5mmol | 2.5mmol | 2.5mmol | |
溶剂 | DMF | DMF | DMF | |
反应时间 | 1hr | 1hr | 1hr | |
反应 | ||||
反应温度 | 50℃ | 50℃ | 在0℃下加料室温下反应 | |
反应时间 | 16hr | 16hr | 16hr | |
结果 | ||||
2,2’-联吡啶基收率% | -- | -- | -- | |
2,4’-联吡啶基收率% | 167mg40% | 90mg23% | 122mg31% | |
4,4’-联吡啶基收率% | -- | -- | -- |
实施例14 | 实施例15 | 实施例16 | ||
催化剂的制备 | ||||
镍配合物催化剂(10或30mol%) | NiCl2(PPh3)2327mg | NiCl2(PPh3)2981g | NiCl2(PPh3)2981mg | |
锌 | 490mg | 490mg | 490mg | |
Et4NI | 1.28g | 384mg(30mol%) | 1.05g(Et4NBr) | |
溶剂 | THF | THF | THF | |
反应时间 | 30min. | 30min. | 30min. | |
原料的制备 | ||||
2-氯吡啶 | 2.5mmol | 2.5mmol | 2.5mmol | |
盐酸4-氯吡啶 | 2.5mmol | 2.5mmol | 2.5mmol | |
三乙胺 | 2.5mmol | 2.5mmol | 2.5mmol | |
溶剂 | DMF | DMF | DMF | |
反应时间 | 1hr | 1hr | 1hr | |
反应 | ||||
反应温度 | 50℃ | 50℃ | 50℃ | |
反应时间 | 16hr | 16hr | 16hr | |
结果 | ||||
2,2’-联吡啶基收率% | -- | -- | -- | |
2,4’-联吡啶基收率% | 98mg25% | 121mg31% | 135mg35% | |
4,4’-联吡啶基收率% | -- | -- | -- |
实施例17 | 实施例18 | ||
催化剂的制备 | |||
镍配合物催化剂(30mol%) | NiCl2(PPh3)21.96g | NiCl2(PPh3)24.9g | |
锌 | 940mg | 2.35g | |
Et4NBr | 2.1g | 5.2g | |
溶剂(浓度:两倍) | THF(10ml) | THF(25ml) | |
反应时间 | 30min. | 30min. | |
原料的制备 | |||
2-氯吡啶 | 5mmol | 12.5mmol | |
盐酸4-氯吡啶 | 5mmol | 12.5mmol | |
三乙胺 | 5mmol | 12.5mmol | |
溶剂 | DMF | THF | |
反应时间 | 1hr | 1hr | |
反应 | |||
反应温度 | 50℃ | 50℃ | |
反应时间 | 16hr | 16hr | |
分离操作 | |||
反应终止溶液 | 4N NH3 50ml | 10N NH3 50ml | |
盐酸 | 2N 20ml | 2N 20ml | |
氨水 | 4N NH3 20ml | 4N NH3 20ml | |
硫酸铜水溶液 | 0.2N 20ml | 0.5N 20ml | |
结果 | |||
2,4’-联吡啶基收率% | 231mg30% | 224mg11% |
Claims (6)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP132631/97 | 1997-05-22 | ||
JP13263197 | 1997-05-22 | ||
JP132631/1997 | 1997-05-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1230950A CN1230950A (zh) | 1999-10-06 |
CN1107054C true CN1107054C (zh) | 2003-04-30 |
Family
ID=15085850
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN98800941A Expired - Fee Related CN1107054C (zh) | 1997-05-22 | 1998-05-22 | 2,4'-联吡啶基衍生物的制备方法和分离方法及其应用 |
Country Status (11)
Country | Link |
---|---|
US (2) | US6096884A (zh) |
EP (1) | EP0966440B1 (zh) |
KR (1) | KR100362958B1 (zh) |
CN (1) | CN1107054C (zh) |
AT (1) | ATE309218T1 (zh) |
AU (1) | AU727647B2 (zh) |
CA (1) | CA2260989C (zh) |
DE (1) | DE69832263T2 (zh) |
ES (1) | ES2247693T3 (zh) |
HU (1) | HUP0001300A3 (zh) |
WO (1) | WO1998052922A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103030595A (zh) * | 2012-12-11 | 2013-04-10 | 安徽国星生物化学有限公司 | 一种2,2'-联吡啶的双碱解合成方法 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE69832263T2 (de) | 1997-05-22 | 2006-06-08 | Daiichi Asubio Pharma Co., Ltd. | Herstellungsverfahren und trennverfahren für 2',4'-dipyridylderivate und herstellverfahren für benzoxazepinderivate und deren salze |
JP4603646B2 (ja) | 1999-11-15 | 2010-12-22 | 富士フイルムファインケミカルズ株式会社 | 新規なジピリジル誘導体 |
JP4603648B2 (ja) * | 1999-11-30 | 2010-12-22 | 富士フイルムファインケミカルズ株式会社 | ピリジン誘導体の製造方法 |
CN103030594A (zh) * | 2012-12-11 | 2013-04-10 | 安徽国星生物化学有限公司 | 一种2,2'-联吡啶的合成方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2176434T3 (es) * | 1995-02-10 | 2002-12-01 | Suntory Ltd | Derivados de benzodiazepina, sales de los mismos, y farmacos que los contienen. |
DE69832263T2 (de) * | 1997-05-22 | 2006-06-08 | Daiichi Asubio Pharma Co., Ltd. | Herstellungsverfahren und trennverfahren für 2',4'-dipyridylderivate und herstellverfahren für benzoxazepinderivate und deren salze |
-
1998
- 1998-05-22 DE DE69832263T patent/DE69832263T2/de not_active Expired - Lifetime
- 1998-05-22 HU HU0001300A patent/HUP0001300A3/hu unknown
- 1998-05-22 ES ES98921776T patent/ES2247693T3/es not_active Expired - Lifetime
- 1998-05-22 CA CA002260989A patent/CA2260989C/en not_active Expired - Fee Related
- 1998-05-22 CN CN98800941A patent/CN1107054C/zh not_active Expired - Fee Related
- 1998-05-22 US US09/230,168 patent/US6096884A/en not_active Expired - Lifetime
- 1998-05-22 WO PCT/JP1998/002264 patent/WO1998052922A1/en active IP Right Grant
- 1998-05-22 AT AT98921776T patent/ATE309218T1/de not_active IP Right Cessation
- 1998-05-22 KR KR1019997000461A patent/KR100362958B1/ko not_active IP Right Cessation
- 1998-05-22 AU AU74505/98A patent/AU727647B2/en not_active Ceased
- 1998-05-22 EP EP98921776A patent/EP0966440B1/en not_active Expired - Lifetime
-
2000
- 2000-06-09 US US09/590,678 patent/US6624308B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
Title |
---|
LIEBIGS,ANN.CHEM.VOL 9.1992.953-960 1992-01-01 Eckhard V.et al "Synthese von unsymmetrischen und" * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103030595A (zh) * | 2012-12-11 | 2013-04-10 | 安徽国星生物化学有限公司 | 一种2,2'-联吡啶的双碱解合成方法 |
Also Published As
Publication number | Publication date |
---|---|
KR100362958B1 (ko) | 2002-11-30 |
CA2260989C (en) | 2005-04-19 |
US20030125547A1 (en) | 2003-07-03 |
ATE309218T1 (de) | 2005-11-15 |
US6624308B2 (en) | 2003-09-23 |
DE69832263D1 (de) | 2005-12-15 |
CA2260989A1 (en) | 1998-11-26 |
DE69832263T2 (de) | 2006-06-08 |
KR20000029467A (ko) | 2000-05-25 |
US6096884A (en) | 2000-08-01 |
HUP0001300A3 (en) | 2002-01-28 |
AU727647B2 (en) | 2000-12-21 |
AU7450598A (en) | 1998-12-11 |
CN1230950A (zh) | 1999-10-06 |
ES2247693T3 (es) | 2006-03-01 |
EP0966440B1 (en) | 2005-11-09 |
EP0966440A1 (en) | 1999-12-29 |
HUP0001300A2 (hu) | 2000-08-28 |
WO1998052922A1 (en) | 1998-11-26 |
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