JP2013525317A5 - - Google Patents
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- Publication number
- JP2013525317A5 JP2013525317A5 JP2013505409A JP2013505409A JP2013525317A5 JP 2013525317 A5 JP2013525317 A5 JP 2013525317A5 JP 2013505409 A JP2013505409 A JP 2013505409A JP 2013505409 A JP2013505409 A JP 2013505409A JP 2013525317 A5 JP2013525317 A5 JP 2013525317A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- bromo
- chloro
- reacting
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 31
- 125000001246 bromo group Chemical group Br* 0.000 claims 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims 10
- 239000002585 base Substances 0.000 claims 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 230000027455 binding Effects 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- 239000007800 oxidant agent Substances 0.000 claims 3
- 230000001590 oxidative Effects 0.000 claims 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N Carbon tetrachloride Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N Triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- KLGZELKXQMTEMM-UHFFFAOYSA-N hydride Chemical compound [H-] KLGZELKXQMTEMM-UHFFFAOYSA-N 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- 125000006414 CCl Chemical group ClC* 0.000 claims 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N Cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- 229910010082 LiAlH Inorganic materials 0.000 claims 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N Meta-Chloroperoxybenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims 1
- 239000005922 Phosphane Substances 0.000 claims 1
- LKYXEULZVGJVTG-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH] LKYXEULZVGJVTG-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 229910000064 phosphane Inorganic materials 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
Claims (8)
- 式Ｉ
ａ）式ＩＩ
ｂ）前記式ＩＩＩの化合物を不活性溶媒の存在下でオキシダントと反応させて式ＩＶ
ｃ）前記式ＩＶの化合物をルイス酸および水素化物源の存在下で反応させて式Ｖ
ｄ）前記式Ｖの化合物を酸化剤、塩基および不活性溶媒の存在下で反応させて式ＶＩ
ｅ）前記式ＶＩの化合物をホスファンおよびＣＣｌ4またはＣＨＣｌ3の存在下で式ＶＩＩ
ｆ１）前記式ＶＩＩの化合物をパラジウムと少なくとも１つの配位子とを含む触媒の存在下でＮＨ3と反応させて式ＶＩＩＩ
ｇ）前記式ＶＩＩＩの化合物を塩基の存在下で式ＩＸ
ｆ２）前記式ＶＩＩ
を包含する、方法。 - ａ）Ｘがブロモである請求項１に記載の式ＩＩの化合物を、式ＩＩＩの化合物と反応させる工程を包含する、請求項１に記載の方法。
- メタ−クロロ−過安息香酸が工程ｂ）におけるオキシダントとして使用される、請求項１に記載の方法。
- ＬｉＡｌＨ4が工程ｃ）において前記水素化物源として使用される、請求項１に記載の方法。
- 前記式ＶＩＩの化合物をパラジウムと少なくとも１つの配位子とを含む触媒の存在下でＮＨ3と反応させて前記式ＶＩＩＩ
- 工程ｅ）において、前記式ＶＩの化合物が、トリフェニルホスファンおよび四塩化炭素の存在下で前記式ＶＩＩの化合物に転化される、請求項１に記載の方法。
- 式ＩＶ
- 式Ｖ
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10160438.7 | 2010-04-20 | ||
| EP10160438 | 2010-04-20 | ||
| PCT/EP2011/055871 WO2011131545A1 (en) | 2010-04-20 | 2011-04-14 | Process for the preparation of pyrazole carboxylic acid amides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013525317A JP2013525317A (ja) | 2013-06-20 |
| JP2013525317A5 true JP2013525317A5 (ja) | 2014-03-13 |
| JP5684896B2 JP5684896B2 (ja) | 2015-03-18 |
Family
ID=44072655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013505409A Active JP5684896B2 (ja) | 2010-04-20 | 2011-04-14 | ピラゾールカルボン酸アミドの調製方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US8519152B2 (ja) |
| EP (1) | EP2560959B1 (ja) |
| JP (1) | JP5684896B2 (ja) |
| CN (1) | CN102906072B (ja) |
| AR (1) | AR080922A1 (ja) |
| BR (1) | BR112012026631B1 (ja) |
| ES (1) | ES2513540T3 (ja) |
| IL (1) | IL222398A (ja) |
| MX (1) | MX2012012005A (ja) |
| TW (1) | TWI428325B (ja) |
| UY (1) | UY33340A (ja) |
| WO (1) | WO2011131545A1 (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112012026456B1 (pt) * | 2010-04-20 | 2017-06-27 | Syngenta Participations Ag | Process for the preparation of carboxylic pyrazole acid amides |
| TWI534126B (zh) * | 2011-01-25 | 2016-05-21 | 先正達合夥公司 | 用於製備吡唑羧酸醯胺之方法 |
| GB201403438D0 (en) | 2014-02-27 | 2014-04-16 | Syngenta Participations Ag | Polymorphs |
| WO2024017788A1 (en) | 2022-07-22 | 2024-01-25 | Syngenta Crop Protection Ag | Solid form of a heterocyclic amide derivative |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH075487B2 (ja) | 1985-11-14 | 1995-01-25 | 住友化学工業株式会社 | １―ブロモ―２―クロロ―４―フルオロベンゼンの製造法 |
| US5093347A (en) | 1991-01-28 | 1992-03-03 | Monsanto Company | 3-difluoromethylpyrazolecarboxamide fungicides, compositions and use |
| US7223879B2 (en) | 1998-07-10 | 2007-05-29 | Massachusetts Institute Of Technology | Ligands for metals and improved metal-catalyzed processes based thereon |
| ES2354374T3 (es) | 2005-10-25 | 2011-03-14 | Syngenta Participations Ag | Derivados de amidas heterocíclicas útiles como microbiocidas. |
| WO2007124907A2 (en) * | 2006-04-27 | 2007-11-08 | Syngenta Participations Ag | Heterocyclyl-carboxylic acid (benzonorbornene-5-yl)amide derivatives as fungicides for agrochemical use |
| BRPI0717985A2 (pt) | 2006-10-25 | 2013-11-12 | Syngenta Ltd | Processo para a produção de bromobenzenos substituídos |
| WO2010072631A1 (en) * | 2008-12-24 | 2010-07-01 | Syngenta Limited | Methods for the preparation of fungicides |
-
2011
- 2011-04-14 US US13/642,406 patent/US8519152B2/en active Active
- 2011-04-14 JP JP2013505409A patent/JP5684896B2/ja active Active
- 2011-04-14 MX MX2012012005A patent/MX2012012005A/es active IP Right Grant
- 2011-04-14 BR BR112012026631-4A patent/BR112012026631B1/pt active IP Right Grant
- 2011-04-14 CN CN201180019785.1A patent/CN102906072B/zh active Active
- 2011-04-14 EP EP11714550.8A patent/EP2560959B1/en active Active
- 2011-04-14 WO PCT/EP2011/055871 patent/WO2011131545A1/en active Application Filing
- 2011-04-14 ES ES11714550.8T patent/ES2513540T3/es active Active
- 2011-04-15 UY UY0001033340A patent/UY33340A/es active IP Right Grant
- 2011-04-18 AR ARP110101326A patent/AR080922A1/es active IP Right Grant
- 2011-04-19 TW TW100113507A patent/TWI428325B/zh active
-
2012
- 2012-10-11 IL IL222398A patent/IL222398A/en active IP Right Grant
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