CN103694168A - 一种6-氯-4-三氟甲基-3-氰基吡啶的制备方法 - Google Patents
一种6-氯-4-三氟甲基-3-氰基吡啶的制备方法 Download PDFInfo
- Publication number
- CN103694168A CN103694168A CN201310644856.8A CN201310644856A CN103694168A CN 103694168 A CN103694168 A CN 103694168A CN 201310644856 A CN201310644856 A CN 201310644856A CN 103694168 A CN103694168 A CN 103694168A
- Authority
- CN
- China
- Prior art keywords
- trifluoromethyl
- nicotinonitrile
- mass parts
- dried
- chloro
- 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
Links
- 238000000034 method Methods 0.000 title abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 60
- OPVSJJVFZHNNHG-UHFFFAOYSA-N 6-oxo-4-(trifluoromethyl)-1H-pyridine-3-carbonitrile Chemical compound OC1=CC(=C(C=N1)C#N)C(F)(F)F OPVSJJVFZHNNHG-UHFFFAOYSA-N 0.000 claims abstract description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- FCYFQKPMNQFMKA-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound FC(F)(F)C1=CC=NC(Cl)=C1C#N FCYFQKPMNQFMKA-UHFFFAOYSA-N 0.000 claims description 30
- 238000001514 detection method Methods 0.000 claims description 24
- 239000012074 organic phase Substances 0.000 claims description 24
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 24
- 239000011734 sodium Substances 0.000 claims description 24
- 238000004809 thin layer chromatography Methods 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- APSXEJUOOOHRGS-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound FC(F)(F)C1=NC=CC=C1C#N APSXEJUOOOHRGS-UHFFFAOYSA-N 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 12
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 12
- 239000012153 distilled water Substances 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- WRXXBTBGBXYHSG-UHFFFAOYSA-N 2,6-dichloro-4-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound FC(F)(F)C1=CC(Cl)=NC(Cl)=C1C#N WRXXBTBGBXYHSG-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 claims description 6
- 229960000583 acetic acid Drugs 0.000 claims description 6
- 239000012362 glacial acetic acid Substances 0.000 claims description 6
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 5
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
- 229910003446 platinum oxide Inorganic materials 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 abstract 4
- CXHDQWICINTWOU-UHFFFAOYSA-N 6-methoxy-4-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound COC1=CC(=C(C=N1)C#N)C(F)(F)F CXHDQWICINTWOU-UHFFFAOYSA-N 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 239000007806 chemical reaction intermediate Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000010960 commercial process Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (2)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310644856.8A CN103694168B (zh) | 2013-12-05 | 2013-12-05 | 一种6-氯-4-三氟甲基-3-氰基吡啶的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310644856.8A CN103694168B (zh) | 2013-12-05 | 2013-12-05 | 一种6-氯-4-三氟甲基-3-氰基吡啶的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103694168A true CN103694168A (zh) | 2014-04-02 |
CN103694168B CN103694168B (zh) | 2015-08-19 |
Family
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Family Applications (1)
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CN201310644856.8A Active CN103694168B (zh) | 2013-12-05 | 2013-12-05 | 一种6-氯-4-三氟甲基-3-氰基吡啶的制备方法 |
Country Status (1)
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CN (1) | CN103694168B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112441966A (zh) * | 2020-12-09 | 2021-03-05 | 山东省农药科学研究院 | 一种由2,3,6-三氯-5-三氟甲基吡啶生产2-氯-3-三氟甲基吡啶的方法 |
CN113912535A (zh) * | 2020-07-07 | 2022-01-11 | 新发药业有限公司 | 一种6-氯-4-三氟甲基-3-氰基吡啶的制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1733729A (zh) * | 2005-08-29 | 2006-02-15 | 浙江工业大学 | 2,6-二甲基吡啶的制备方法 |
CN101039577A (zh) * | 2004-10-12 | 2007-09-19 | 神经能质公司 | 经取代的二芳基喹啉-4-基胺类似物 |
WO2009089263A2 (en) * | 2008-01-07 | 2009-07-16 | Ardea Biosciences Inc. | Novel compositions and methods of use |
CN102118968A (zh) * | 2008-06-10 | 2011-07-06 | 雅培制药有限公司 | 新的三环化合物 |
CN102153507A (zh) * | 2011-03-13 | 2011-08-17 | 联化科技股份有限公司 | 一种2,3-二氯吡啶的制备方法 |
-
2013
- 2013-12-05 CN CN201310644856.8A patent/CN103694168B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101039577A (zh) * | 2004-10-12 | 2007-09-19 | 神经能质公司 | 经取代的二芳基喹啉-4-基胺类似物 |
CN1733729A (zh) * | 2005-08-29 | 2006-02-15 | 浙江工业大学 | 2,6-二甲基吡啶的制备方法 |
WO2009089263A2 (en) * | 2008-01-07 | 2009-07-16 | Ardea Biosciences Inc. | Novel compositions and methods of use |
CN102118968A (zh) * | 2008-06-10 | 2011-07-06 | 雅培制药有限公司 | 新的三环化合物 |
CN102153507A (zh) * | 2011-03-13 | 2011-08-17 | 联化科技股份有限公司 | 一种2,3-二氯吡啶的制备方法 |
Non-Patent Citations (1)
Title |
---|
ALEXANDER S. KISELYOV: "Reaction of N-fluoropyridinium fluoride with isonitriles:a convenient route to picolinamides", 《TETRAHEDRON LETTERS》, vol. 46, 1 February 2005 (2005-02-01), pages 2279 - 2282 * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113912535A (zh) * | 2020-07-07 | 2022-01-11 | 新发药业有限公司 | 一种6-氯-4-三氟甲基-3-氰基吡啶的制备方法 |
CN113912535B (zh) * | 2020-07-07 | 2023-04-07 | 新发药业有限公司 | 一种6-氯-4-三氟甲基-3-氰基吡啶的制备方法 |
CN112441966A (zh) * | 2020-12-09 | 2021-03-05 | 山东省农药科学研究院 | 一种由2,3,6-三氯-5-三氟甲基吡啶生产2-氯-3-三氟甲基吡啶的方法 |
Also Published As
Publication number | Publication date |
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CN103694168B (zh) | 2015-08-19 |
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C53 | Correction of patent of invention or patent application | ||
CB02 | Change of applicant information |
Address after: 550014, 388, new material industrial park, Baiyun District, Guizhou, Guiyang Applicant after: GUIZHOU WYLTON JINGLIN ELECTRONIC MATERIAL CO.,LTD. Address before: 550014, 388, new material industrial park, Baiyun District, Guizhou, Guiyang Applicant before: Guizhou Wylton Jinglin Electronic Materials Co.,Ltd. |
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Free format text: CORRECT: APPLICANT; FROM: GUIZHOU WYLTON JINLIN ELECTRONIC MATERIALS CO., LTD. TO: GUIZHOU WYLTON JINGLIN ELECTRONIC MATERIALS CO., LTD. |
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C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A preparation method of 6-chloro-4-trifluoromethyl-3-cyanopyridine Effective date of registration: 20211103 Granted publication date: 20150819 Pledgee: Guiyang Jinyang sub branch of China Construction Bank Co.,Ltd. Pledgor: GUIZHOU WYLTON JINGLIN ELECTRONIC MATERIAL CO.,LTD. Registration number: Y2021520000016 |
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PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20230704 Granted publication date: 20150819 Pledgee: Guiyang Jinyang sub branch of China Construction Bank Co.,Ltd. Pledgor: GUIZHOU WYLTON JINGLIN ELECTRONIC MATERIAL CO.,LTD. Registration number: Y2021520000016 |