JP2018516843A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018516843A5 JP2018516843A5 JP2017547544A JP2017547544A JP2018516843A5 JP 2018516843 A5 JP2018516843 A5 JP 2018516843A5 JP 2017547544 A JP2017547544 A JP 2017547544A JP 2017547544 A JP2017547544 A JP 2017547544A JP 2018516843 A5 JP2018516843 A5 JP 2018516843A5
- Authority
- JP
- Japan
- Prior art keywords
- palladium catalyst
- suzuki coupling
- formula
- alkyl
- coupling reaction
- 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.)
- Withdrawn
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 90
- 238000000034 method Methods 0.000 claims description 68
- 229910052763 palladium Inorganic materials 0.000 claims description 45
- 239000003054 catalyst Substances 0.000 claims description 36
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000002244 precipitate Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 10
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 9
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 9
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 9
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 9
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 9
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 125000005110 aryl thio group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 9
- QOJNAEPFSUYAFL-UHFFFAOYSA-N 5,6-dichloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)C(Cl)=N1 QOJNAEPFSUYAFL-UHFFFAOYSA-N 0.000 claims description 8
- 239000012452 mother liquor Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000003880 polar aprotic solvent Substances 0.000 claims description 7
- GDJCQSNQOHRAGY-UHFFFAOYSA-N (4-chloro-2-fluoro-3-methoxyphenyl)boronic acid Chemical compound COC1=C(Cl)C=CC(B(O)O)=C1F GDJCQSNQOHRAGY-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 238000005191 phase separation Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 239000003446 ligand Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 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 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 230000001172 regenerating effect Effects 0.000 claims description 3
- LHGHJAGVMNLDGA-UHFFFAOYSA-N 4,5,6-trichloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=C(Cl)C(Cl)=N1 LHGHJAGVMNLDGA-UHFFFAOYSA-N 0.000 claims description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 2
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims 6
- 239000013049 sediment Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000000262 haloalkenyl group Chemical group 0.000 description 6
- 125000000232 haloalkynyl group Chemical group 0.000 description 6
- 238000005406 washing Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562165502P | 2015-05-22 | 2015-05-22 | |
| US62/165,502 | 2015-05-22 | ||
| PCT/US2016/033429 WO2016191245A1 (en) | 2015-05-22 | 2016-05-20 | Recovery and/or reuse of palladium catalyst after a suzuki coupling |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018516843A JP2018516843A (ja) | 2018-06-28 |
| JP2018516843A5 true JP2018516843A5 (enExample) | 2019-06-20 |
Family
ID=57325189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017547544A Withdrawn JP2018516843A (ja) | 2015-05-22 | 2016-05-20 | Ｓｕｚｕｋｉカップリング後のパラジウムの回収及び／または再利用 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20160340311A1 (enExample) |
| EP (1) | EP3297436A4 (enExample) |
| JP (1) | JP2018516843A (enExample) |
| KR (1) | KR20180011050A (enExample) |
| CN (1) | CN107426998A (enExample) |
| AR (1) | AR104734A1 (enExample) |
| BR (1) | BR112017019207A2 (enExample) |
| CA (1) | CA2978972A1 (enExample) |
| CO (1) | CO2017008865A2 (enExample) |
| IL (1) | IL254346A (enExample) |
| MX (1) | MX2017011447A (enExample) |
| TW (1) | TW201718503A (enExample) |
| WO (1) | WO2016191245A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT3762368T (pt) | 2018-03-08 | 2022-05-06 | Incyte Corp | Compostos de aminopirazina diol como inibidores de pi3k-y |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| CN110041373A (zh) * | 2019-04-29 | 2019-07-23 | 江苏万年长药业有限公司 | 一种雷迪帕韦中间体制备过程中贵金属催化剂的回收方法 |
| JP2021070684A (ja) * | 2019-10-30 | 2021-05-06 | 東ソー株式会社 | ハロゲン化合物の製造方法 |
| KR102419596B1 (ko) | 2020-10-06 | 2022-07-08 | 김창기 | 팔라듐이 포함된 슬러지 회수 장치 |
| CN114921657A (zh) * | 2022-05-06 | 2022-08-19 | 浙江微通催化新材料有限公司 | 一种从含铯盐的废钯催化剂中回收铯和钯的方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641076A (en) * | 1970-08-24 | 1972-02-08 | Union Oil Co | Catalyst recovery |
| US4791226A (en) * | 1983-06-23 | 1988-12-13 | Amoco Corporation | Catalyst and process for purification of crude terephthalic acid |
| AR037228A1 (es) * | 2001-07-30 | 2004-11-03 | Dow Agrosciences Llc | Compuestos del acido 6-(aril o heteroaril)-4-aminopicolinico, composicion herbicida que los comprende y metodo para controlar vegetacion no deseada |
| US20060258875A1 (en) * | 2005-05-10 | 2006-11-16 | Clementine Reyes | Methods for manufacturing supported nanocatalysts and methods for using supported nanocatalysts |
| FR2914867B1 (fr) * | 2007-04-16 | 2009-06-05 | Univ Haute Alsace Etablissemen | Procede de synthese de catalyseurs heterogenes au palladium, catalyseurs obtenus et utilisations de ces derniers. |
| WO2011020900A2 (en) * | 2009-08-21 | 2011-02-24 | Technische Universität Berlin | A process for preparing biaryl compounds in a suzuki type reaction allowing product isolation and catalyst recycling in one step |
| PL2797890T3 (pl) * | 2011-12-30 | 2017-06-30 | Dow Agrosciences Llc | Sposoby wytwarzania 4-amino-3-chloro-6-(4-chloro-2-fluoro-3- metoksyfenylo)pirydyno-2-karboksylanu metylu |
| JP6290788B2 (ja) * | 2011-12-30 | 2018-03-07 | ダウ アグロサイエンシィズ エルエルシー | ４−クロロ−２−フルオロ−３−置換−フェニルボロン酸ピナコールエステルの形成方法およびその使用方法 |
| US8703953B2 (en) * | 2012-03-09 | 2014-04-22 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
-
2016
- 2016-05-20 US US15/159,973 patent/US20160340311A1/en not_active Abandoned
- 2016-05-20 EP EP16800528.8A patent/EP3297436A4/en not_active Withdrawn
- 2016-05-20 MX MX2017011447A patent/MX2017011447A/es unknown
- 2016-05-20 BR BR112017019207A patent/BR112017019207A2/pt not_active Application Discontinuation
- 2016-05-20 KR KR1020177025293A patent/KR20180011050A/ko not_active Withdrawn
- 2016-05-20 CA CA2978972A patent/CA2978972A1/en not_active Abandoned
- 2016-05-20 CN CN201680014261.6A patent/CN107426998A/zh active Pending
- 2016-05-20 JP JP2017547544A patent/JP2018516843A/ja not_active Withdrawn
- 2016-05-20 WO PCT/US2016/033429 patent/WO2016191245A1/en not_active Ceased
- 2016-05-23 AR ARP160101498A patent/AR104734A1/es unknown
- 2016-05-23 TW TW105115960A patent/TW201718503A/zh unknown
-
2017
- 2017-08-30 CO CONC2017/0008865A patent/CO2017008865A2/es unknown
- 2017-09-06 IL IL254346A patent/IL254346A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018516843A5 (enExample) | ||
| JP2018516843A (ja) | Ｓｕｚｕｋｉカップリング後のパラジウムの回収及び／または再利用 | |
| CN107200705B (zh) | 一种3-硝基-2-吲哚酮衍生物的制备方法 | |
| JP6067228B2 (ja) | エトリコキシブの中間体、１−（６−メチルピリジン−３−イル）−２−［４−（メチルスルホニル）フェニル］エタノンの調製方法の改良 | |
| CN101402537B (zh) | 2-吡啶-β酮类化合物的应用 | |
| JP2019142828A (ja) | ４，５−ジシアノ−２−（フルオロアルキル）イミダゾールの製造方法 | |
| US8063226B2 (en) | Process for preparing 2-amino-4-(haloalkyl) pyridine derivatives by cyclizing suitable nitrile precursors with nitrogen compounds | |
| JP6763401B2 (ja) | ベンズオキサゾール化合物の製造方法 | |
| JP2006514075A (ja) | ２−アミノメチルピリジン誘導体の製造方法 | |
| JP4764586B2 (ja) | ２−シアノピリジンの製造方法 | |
| JP4167848B2 (ja) | ビアリール化合物の製造法 | |
| JP5546872B2 (ja) | Ｎ，ｎ，ｎ’，ｎ’−テトラアリールベンジジン誘導体の製造方法 | |
| JP2016525094A5 (enExample) | ||
| WO2014093566A1 (en) | An improved process for the removal of palladium from 4-amino-3-halo-5-fluoro-6-(aryl) pyridine-2-carboxylates and 4-amino-3-halo-6-(aryl)pyridine-2-carboxylates | |
| CN104356053A (zh) | 2-(3-卤素苯基)吡啶类衍生物的制备方法 | |
| CN104379564B (zh) | 通过2,2-二氟乙胺的烷基化制备2,2-二氟乙胺衍生物的方法 | |
| JP5151180B2 (ja) | ３，３’，４，４’−シクロヘキセニルフェニルテトラカルボン酸化合物群及び３，３’，４，４’−ビフェニルテトラカルボン酸化合物の製法 | |
| CN107954979B (zh) | 一种合成α-乙基吡咯烷-2-酮取代的吡啶类化合物的方法 | |
| JP6533233B2 (ja) | ２，２−ジフルオロエチルアミンをアルキル化することによりｎ−［（６−クロロピリジノ−３−イル）メチル］−２，２−ジフルオロエタン−１−アミンを調製する方法 | |
| JP4329325B2 (ja) | ジアリルシアヌレートのモノアルカリ金属塩の製造方法 | |
| CN102648190B (zh) | 5-(氨基甲基)-2-氯噻唑的制造方法 | |
| JP5424650B2 (ja) | ［４−（２−ジフェニルホスファニルナフタレン−１−イル）フタラジン−１−イル］−（１−フェニルエチル）アミンの光学活性体の製造方法 | |
| CN121161313A (en) | Preparation method of trisubstituted diene compound | |
| JP2004083530A (ja) | ビアリール化合物の製造法 | |
| JPWO2018025590A1 (ja) | 含窒素複素環化合物の製造方法及び含窒素複素環化合物 |