JP2016535033A5 - - Google Patents
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- Publication number
- JP2016535033A5 JP2016535033A5 JP2016526839A JP2016526839A JP2016535033A5 JP 2016535033 A5 JP2016535033 A5 JP 2016535033A5 JP 2016526839 A JP2016526839 A JP 2016526839A JP 2016526839 A JP2016526839 A JP 2016526839A JP 2016535033 A5 JP2016535033 A5 JP 2016535033A5
- Authority
- JP
- Japan
- Prior art keywords
- boronic acid
- chiral
- represented
- formula
- primary
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 claims 64
- 125000005620 boronic acid group Chemical group 0.000 claims 32
- 239000000203 mixture Substances 0.000 claims 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 12
- 125000005621 boronate group Chemical class 0.000 claims 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 8
- 239000003880 polar aprotic solvent Substances 0.000 claims 8
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims 7
- 125000000962 organic group Chemical group 0.000 claims 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 4
- 239000003377 acid catalyst Substances 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 230000003301 hydrolyzing effect Effects 0.000 claims 3
- 239000003446 ligand Substances 0.000 claims 3
- QAUCEEIOCLCCFG-UHFFFAOYSA-N trihydroxy borate Chemical class OOB(OO)OO QAUCEEIOCLCCFG-UHFFFAOYSA-N 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 239000002841 Lewis acid Substances 0.000 claims 2
- -1 benzylcyclopentyliminodiacetic acid Chemical compound 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- NBZBKCUXIYYUSX-UHFFFAOYSA-N iminodiacetic acid Chemical compound OC(=O)CNCC(O)=O NBZBKCUXIYYUSX-UHFFFAOYSA-N 0.000 claims 2
- 150000007517 lewis acids Chemical class 0.000 claims 2
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical group C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 claims 2
- XWSGEVNYFYKXCP-UHFFFAOYSA-N 2-[carboxymethyl(methyl)amino]acetic acid Chemical group OC(=O)CN(C)CC(O)=O XWSGEVNYFYKXCP-UHFFFAOYSA-N 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 241001139947 Mida Species 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001502 aryl halides Chemical class 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000000532 dioxanyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000002407 reforming Methods 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361899296P | 2013-11-03 | 2013-11-03 | |
| US61/899,296 | 2013-11-03 | ||
| PCT/US2014/063692 WO2015066612A2 (en) | 2013-11-03 | 2014-11-03 | Cross-coupling of unactivated secondary boronic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016535033A JP2016535033A (ja) | 2016-11-10 |
| JP2016535033A5 true JP2016535033A5 (enExample) | 2018-02-08 |
Family
ID=51952004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016526839A Pending JP2016535033A (ja) | 2013-11-03 | 2014-11-03 | 活性化されていない第二級ボロン酸のクロスカップリング |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US10072028B2 (enExample) |
| EP (1) | EP3063154B1 (enExample) |
| JP (1) | JP2016535033A (enExample) |
| WO (1) | WO2015066612A2 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6866583B2 (ja) * | 2016-07-05 | 2021-04-28 | Dic株式会社 | 液晶化合物 |
| US10370393B2 (en) | 2017-04-21 | 2019-08-06 | The Board Of Trustees Of The University Of Illinois | Stereoretentive cross-coupling of boronic acids |
| JP7553547B2 (ja) * | 2020-03-31 | 2024-09-18 | エヌ・イーケムキャット株式会社 | 芳香族化合物の製造方法 |
| WO2022031998A2 (en) * | 2020-08-05 | 2022-02-10 | Skyhawk Therapeutics, Inc. | Process for the preparation of intermediates useful in the preparation of compounds that modulate splicing |
| WO2022032007A2 (en) * | 2020-08-05 | 2022-02-10 | Skyhawk Therapeutics, Inc. | Process for the preparation of intermediates useful in the preparation of compounds that modulate splicing |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2551916T3 (es) | 2007-07-23 | 2015-11-24 | The Board Of Trustees Of The University Of Illinois | Sistema para controlar la reactividad de los ácidos borónicos |
| JP5501656B2 (ja) * | 2008-05-16 | 2014-05-28 | 株式会社半導体エネルギー研究所 | 組成物、薄膜の作製方法、及び発光素子の作製方法 |
| US8338601B2 (en) | 2008-09-26 | 2012-12-25 | Board Of Trustees Of The University Of Illinois | Slow release of organoboronic acids in cross-coupling reactions |
| WO2011103435A2 (en) | 2010-02-18 | 2011-08-25 | The Board Of Trustees Of The University Of Illinois | Methods for forming protected organoboronic acids |
| US9238597B2 (en) | 2010-07-23 | 2016-01-19 | The Board Of Trustees Of The University Of Illinois | Apparatus and methods for the automated synthesis of small molecules |
| WO2012149182A2 (en) | 2011-04-27 | 2012-11-01 | The Board Of Trustees Of The University Of Illinois | Automated synthesis of small molecules using chiral, non-racemic boronates |
| EP2647628A1 (en) * | 2012-04-02 | 2013-10-09 | Almirall, S.A. | Substituted tricyclic compounds with activity towards ep1 receptors |
-
2014
- 2014-11-03 WO PCT/US2014/063692 patent/WO2015066612A2/en not_active Ceased
- 2014-11-03 EP EP14802743.6A patent/EP3063154B1/en active Active
- 2014-11-03 JP JP2016526839A patent/JP2016535033A/ja active Pending
- 2014-11-03 US US15/034,102 patent/US10072028B2/en active Active
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