WO2011124827A1 - Procede de preparation de derives de sulfonamido-benzofurane - Google Patents
Procede de preparation de derives de sulfonamido-benzofurane Download PDFInfo
- Publication number
- WO2011124827A1 WO2011124827A1 PCT/FR2011/050707 FR2011050707W WO2011124827A1 WO 2011124827 A1 WO2011124827 A1 WO 2011124827A1 FR 2011050707 W FR2011050707 W FR 2011050707W WO 2011124827 A1 WO2011124827 A1 WO 2011124827A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- benzofuran
- formula
- general formula
- alkyl
- Prior art date
Links
- 0 *c(c1c2)c(*)[o]c1ccc2NS(*)(=O)=O Chemical compound *c(c1c2)c(*)[o]c1ccc2NS(*)(=O)=O 0.000 description 3
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B45/00—Formation or introduction of functional groups containing sulfur
- C07B45/04—Formation or introduction of functional groups containing sulfur of sulfonyl or sulfinyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Definitions
- the present invention relates generally to a process for the preparation of sulfonamido-benzofuran derivatives.
- the invention relates to a process for the preparation of 5-sulfonamido-benzofuran derivatives of general formula:
- R represents an alkyl or aryl group and R 1 and R 2 , which may be identical or different, each represent hydrogen or an alkyl or aryl group.
- Ri or R 2 represents in particular an alkyl group, linear or branched dC 8 including a linear alkyl group or branched C 1 -C 4 such as methyl, ethyl, n-propyl isopropyl, n-butyl or tert-butyl or a substituted or unsubstituted phenyl group.
- 2-n-butyl-5-sulfonamido-benzofuran described in patent application WO 02/48132 has proved particularly useful as an intermediate product for the final preparation of aminoalkoxybenzoyl-benzofuran derivatives especially for the preparation of 2-n-butyl-3- ⁇ 4- [3- (di-n-butylamino) propoxy] -benzoyl ⁇ -5-methanesulfonamidobenzofuran commonly known as dronedarone and its pharmaceutically acceptable salts.
- This methanesulphonamido-benzofuran derivative has been described in patent EP0471609 as well as its therapeutic applications, particularly in the cardiovascular field where it has proved particularly advantageous for example as an antiarrhythmic agent.
- the 5-sulfonamido-benzofuran derivatives of formula I can be prepared by coupling a benzofuran derivative of general formula:
- R 1 and R 2 have the same meaning as before and X represents chlorine, bromine or iodine or a sulphonate group of general formula:
- R 3 represents a trifluoromethane (-CF 3 ) or imidazolyl group, with a sulphonamide derivative of general formula:
- R has the same meaning as above and in the presence of a basic agent and a catalyst system formed of a complex between a palladium compound and a ligand, which provides the desired compounds.
- the palladium complex used in the process of the invention is generally in the form of a palladium (0) compound such as, for example:
- biarylphosphines are, in general, substituted in various ways.
- the aryl ring such as phenyl, which does not carry the phosphorus atom can be mono- or especially polysubstituted, for example by the isopropyl group, whereas the aryl ring, in particular phenyl, carrying the phosphorus atom can to be, moreover, mono- or polysubstituted.
- this aryl ring has no substituents other than the phosphorus atom.
- the phosphorus atom can itself be substituted, for example mono- or, especially, disubstituted, for example by alkyl or cycloalkyl groups such as tert-butyl or cyclohexyl.
- L1 ligand 2- (di-tert-butylphosphino) -2 ', 4', 6'-triisopropyl-1,1'-biphenyl, hereinafter referred to as "L1 ligand",
- L2 ligand 2- (Dicyclohexylphosphino) -2 ', 4', 6'-triisopropyl-1,1'-biphenyl, hereinafter referred to as "L2 ligand",
- L3 ligand 2- (Dicyclohexylphosphino) -2 ', 6'-dimethoxy-1,1'-biphenyl, hereinafter referred to as "L3 ligand",
- L4 ligand 2- (di-tert-butylphosphino) -3,4,5,6-tetramethyl-2 ', 4', 6'-triisopropyl-1,1'-biphenyl, hereinafter referred to as "L4 ligand”.
- the ligand L1 is particularly advantageous.
- the basic agent used in the process according to the invention may be chosen from, in particular, alcoholates, but more generally from weaker bases such as phosphates or carbonates, for example alkali metal phosphates or alkali metal carbonates. such as tripotassium phosphate, potassium carbonate or cesium carbonate.
- the coupling reaction is carried out hot, for example at a temperature between 60 ° C and 120 ° C, and in a suitable solvent.
- This may be an alcohol such as for example tert-butanol, an ether such as for example tetrahydrofuran or dioxane or a hydrocarbon, preferably aromatic, such as for example toluene.
- dioxane is a solvent of choice in the context of the present invention.
- the starting compounds of formula II can be prepared in different ways according to their chemical structure, as described below.
- the ester of formula VII is then saponified in a solvent, especially an ether, and in the presence of a suitable basic agent such as an alkali metal hydroxide to form the corresponding salt of a carboxylic acid derivative which is then treated with a strong acid, in a solvent such as an aromatic hydrocarbon, to give the carboxylic acid derivative of formula VIII wherein R 1, R 2 and X 1 have the same meaning as above.
- a suitable basic agent such as an alkali metal hydroxide
- the carboxylic acid derivative of formula VIII is then cyclized by heating in the presence of a benzenesulphonyl halide and an acid acceptor such as a tertiary amine, the reaction generally taking place by heating in a solvent such as an aromatic hydrocarbon, to give the compounds of formula IX wherein X 1, R 1 and R 2 have the same meaning as before, i.e. the desired compounds of formula II.
- R ' 3 represents a trifluoromethane or imidazolyl group represent another object of the present invention.
- the temperature of the reaction medium is reduced to 20% and then 100 ml of deionized water are added slowly, leading to the demixing of an oil.
- This oil is decanted and separated from the aqueous phase, then washed with 100 ml of water. After decantation and separation, the oil is diluted with 60 ml of toluene and this organic phase is washed again with 100 ml of deionized water. This last aqueous phase is counter-extracted 60 ml of ethyl acetate.
- the organic phases are combined and then concentrated on a rotary evaporator to obtain 34.9 g of the desired compound X in the form of an orange-yellow oil.
- the temperature of the reaction medium is brought to 20 ° C. and 25.5 g of sodium chloride (0.43 mol) in 130 ml of deionized water and then 270 ml of toluene are added.
- the reaction medium is acidified by slowly adding 20 ml of a 37% hydrochloric acid solution, without exceeding 25%.
- the two phases are decanted and separated, then the organic phase is washed with 80 ml of deionized water. After separation of the phases, the organic phase is concentrated under vacuum on a rotary evaporator to yield 54.7 g of a red oil, which crystallizes in the cold state.
- the temperature of the reaction medium is brought to 20 ° C.
- Excess benzenesulfonyl chloride is destroyed by the addition of 250 ml of 5% aqueous sodium hydroxide solution.
- the phases are decanted and separated and the organic phase is washed with a mixture of 70 ml of deionized water and 6.8 ml of 37% hydrochloric acid.
- the phases are decanted and separated and the organic phase is washed with 75 ml of deionized water.
- the organic phase is washed with a solution of 7.73 g of sodium hydroxide dissolved in 67 ml of deionized water.
- the phases are decanted and separated then the organic phase is washed with a solution of 7.53 g of sodium chloride in 70 ml of deionized water.
- the pH of the aqueous phase is adjusted to between 5 and 8 with a 7% hydrochloric acid solution.
- the phases are decanted and separated then the organic phase is concentrated on a rotary evaporator to yield 37.2 g of a brown oil.
- This oil is purified by chromatography on silica gel (eluent: methylcyclohexane / ethyl acetate: 80/20) to give 24.3 g of the desired compound XII as a yellow oil.
- reaction medium is then stirred and heated at reflux of the solvent or at 100 ° C for 24 hours, while monitoring the evolution of the reaction by TLC (eluent: ethyl acetate / methylcyclohexane 20/80) or by HPLC.
- TLC eluent: ethyl acetate / methylcyclohexane 20/80
- HPLC HPLC
- reaction medium is then stirred and heated at 100 ° C. for 24 hours.
- the reaction medium is then diluted with 40 ml of ethyl acetate and the first crystallization stream is filtered on Buchner. After isolation of a second jet, 3.6 g of desired compound I are isolated as a snow-white powder.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SG2012071965A SG184315A1 (en) | 2010-03-30 | 2011-03-30 | Process for preparing sulfonamido-benzofuran derivatives |
US13/638,500 US9334254B2 (en) | 2010-03-30 | 2011-03-30 | Process for preparing sulfonamidobenzofuran derivatives |
RU2012146086/04A RU2012146086A (ru) | 2010-03-30 | 2011-03-30 | Способ получения производных сульфонамидобензофурана |
CN201180026858XA CN102933568A (zh) | 2010-03-30 | 2011-03-30 | 制备磺酰氨基苯并呋喃衍生物的方法 |
MX2012011344A MX2012011344A (es) | 2010-03-30 | 2011-03-30 | Proceso para preparar derivados de sulfonamido-benzofurano. |
CA2794436A CA2794436A1 (fr) | 2010-03-30 | 2011-03-30 | Procede de preparation de derives de sulfonamido-benzofurane |
BR112012024792A BR112012024792A2 (pt) | 2010-03-30 | 2011-03-30 | processo de preparo de derivados de sulfonamido-benzofurano |
JP2013501913A JP2013523699A (ja) | 2010-03-30 | 2011-03-30 | スルホンアミドベンゾフラン誘導体の調製方法 |
KR1020127028218A KR20130018809A (ko) | 2010-03-30 | 2011-03-30 | 술폰아미도―벤조푸란 유도체의 제조 방법 |
AU2011236671A AU2011236671A1 (en) | 2010-03-30 | 2011-03-30 | Process for preparing sulfonamido-benzofuran derivatives |
EP11720315A EP2552899A1 (fr) | 2010-03-30 | 2011-03-30 | Procede de preparation de derives de sulfonamido-benzofurane |
IL222191A IL222191A0 (en) | 2010-03-30 | 2012-09-27 | Process for preparing sulfonamido-benzofuran derivatives |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1052334A FR2958290B1 (fr) | 2010-03-30 | 2010-03-30 | Procede de preparation de derives de sulfonamido-benzofurane |
FR1052334 | 2010-03-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2011124827A1 true WO2011124827A1 (fr) | 2011-10-13 |
Family
ID=43430902
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2011/050707 WO2011124827A1 (fr) | 2010-03-30 | 2011-03-30 | Procede de preparation de derives de sulfonamido-benzofurane |
Country Status (14)
Country | Link |
---|---|
US (1) | US9334254B2 (fr) |
EP (1) | EP2552899A1 (fr) |
JP (1) | JP2013523699A (fr) |
KR (1) | KR20130018809A (fr) |
CN (1) | CN102933568A (fr) |
AU (1) | AU2011236671A1 (fr) |
BR (1) | BR112012024792A2 (fr) |
CA (1) | CA2794436A1 (fr) |
FR (1) | FR2958290B1 (fr) |
IL (1) | IL222191A0 (fr) |
MX (1) | MX2012011344A (fr) |
RU (1) | RU2012146086A (fr) |
SG (1) | SG184315A1 (fr) |
WO (1) | WO2011124827A1 (fr) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HUP0900759A2 (en) | 2009-12-08 | 2011-11-28 | Sanofi Aventis | Novel process for producing dronedarone |
HUP1000010A2 (en) | 2010-01-08 | 2011-11-28 | Sanofi Sa | Process for producing dronedarone |
FR2957079B1 (fr) | 2010-03-02 | 2012-07-27 | Sanofi Aventis | Procede de synthese de derives de cetobenzofurane |
FR2958291B1 (fr) | 2010-04-01 | 2013-07-05 | Sanofi Aventis | Procede de preparation de derives d'amino-benzofurane |
HUP1000330A2 (en) | 2010-06-18 | 2011-12-28 | Sanofi Sa | Process for the preparation of dronedarone and the novel intermediates |
HUP1100165A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Process for preparation of dronedarone by n-butylation |
HUP1100167A2 (en) | 2011-03-29 | 2012-11-28 | Sanofi Sa | Process for preparation of dronedarone by mesylation |
FR2983198B1 (fr) | 2011-11-29 | 2013-11-15 | Sanofi Sa | Procede de preparation de derives de 5-amino-benzoyl-benzofurane |
EP2617718A1 (fr) | 2012-01-20 | 2013-07-24 | Sanofi | Procédé de préparation de dronédarone à l'aide d'un réactif dibutylaminopropanol |
US9221778B2 (en) | 2012-02-13 | 2015-12-29 | Sanofi | Process for preparation of dronedarone by removal of hydroxyl group |
US9249119B2 (en) | 2012-02-14 | 2016-02-02 | Sanofi | Process for the preparation of dronedarone by oxidation of a sulphenyl group |
WO2013124745A1 (fr) | 2012-02-22 | 2013-08-29 | Sanofi | Procédé pour la préparation de dronédarone par l'oxydation d'un groupe hydroxyle |
WO2013178337A1 (fr) | 2012-05-31 | 2013-12-05 | Sanofi | Procédé pour la préparation de dronédarone par réaction de grignard |
CN114456135A (zh) * | 2022-03-18 | 2022-05-10 | 江苏慧聚药业股份有限公司 | 决奈达隆的制备 |
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UY32657A (es) | 2009-05-27 | 2010-12-31 | Sanofi Aventis | Procedimiento para la fabricación de productos intermedios de dronedarona |
UY32656A (es) | 2009-05-27 | 2010-12-31 | Sanofi Aventis | Procedimiento para producir benzofuranos |
CN101993427B (zh) | 2009-08-26 | 2012-10-10 | 成都伊诺达博医药科技有限公司 | 一种制备决奈达隆的方法 |
HUP0900759A2 (en) | 2009-12-08 | 2011-11-28 | Sanofi Aventis | Novel process for producing dronedarone |
HUP1000010A2 (en) | 2010-01-08 | 2011-11-28 | Sanofi Sa | Process for producing dronedarone |
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IT1398317B1 (it) | 2010-02-23 | 2013-02-22 | Chimico Internaz Spa Lab | Nuovo procedimento per la preparazione del dronedarone. |
FR2957079B1 (fr) | 2010-03-02 | 2012-07-27 | Sanofi Aventis | Procede de synthese de derives de cetobenzofurane |
FR2958289B1 (fr) * | 2010-03-30 | 2012-06-15 | Sanofi Aventis | Procede de preparation de derives de 3-ceto-benzofurane |
FR2958291B1 (fr) | 2010-04-01 | 2013-07-05 | Sanofi Aventis | Procede de preparation de derives d'amino-benzofurane |
CN101838252B (zh) | 2010-05-27 | 2016-05-04 | 北京德众万全医药科技有限公司 | 2-正丁基-5-取代氨基苯并呋喃及其制备方法 |
HUP1000330A2 (en) | 2010-06-18 | 2011-12-28 | Sanofi Sa | Process for the preparation of dronedarone and the novel intermediates |
WO2012004658A2 (fr) | 2010-07-09 | 2012-01-12 | Frichem Private Limited | Procédé de préparation du n-[2-butyl-3-[4-[3-(dibutylamino)propoxy]benzoyl]-5-benzofuranyl]méthanesulfonamide, sels d'addition acide et produit de celui-ci |
FR2962731B1 (fr) | 2010-07-19 | 2012-08-17 | Sanofi Aventis | Procede de preparation de derives d'amino-benzoyl-benzofurane |
FR2963006B1 (fr) | 2010-07-21 | 2013-03-15 | Sanofi Aventis | Procede de preparation de derives de nitro-benzofurane |
HUP1000386A2 (en) | 2010-07-22 | 2012-05-29 | Sanofi Sa | Novel process for producing dronedarone |
WO2012032545A1 (fr) | 2010-09-08 | 2012-03-15 | Cadila Healthcare Limited | Procédé pour préparer un dérivé de benzofurane et des produits intermédiaires de celui-ci |
FR2973027A1 (fr) | 2011-03-24 | 2012-09-28 | Sanofi Aventis | Procede de synthese de derives de cetobenzofurane |
HUP1100166A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Reductive amination process for preparation of dronedarone using amine intermediary compound |
HUP1100167A2 (en) | 2011-03-29 | 2012-11-28 | Sanofi Sa | Process for preparation of dronedarone by mesylation |
HUP1100165A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Process for preparation of dronedarone by n-butylation |
WO2013014480A1 (fr) | 2011-07-26 | 2013-01-31 | Sanofi | Procédé de préparation de dronédarone utilisant un composé intermédiaire amide |
WO2013014478A1 (fr) | 2011-07-26 | 2013-01-31 | Sanofi | Procédé d'amination réductrice pour la préparation de dronédarone, utilisant un composé intermédiaire carboxyle |
WO2013014479A1 (fr) | 2011-07-26 | 2013-01-31 | Sanofi | Procédé d'amination réductrice pour la préparation de dronédarone, utilisant un composé intermédiaire aldéhyde |
FR2983198B1 (fr) | 2011-11-29 | 2013-11-15 | Sanofi Sa | Procede de preparation de derives de 5-amino-benzoyl-benzofurane |
EP2617718A1 (fr) | 2012-01-20 | 2013-07-24 | Sanofi | Procédé de préparation de dronédarone à l'aide d'un réactif dibutylaminopropanol |
US9221778B2 (en) | 2012-02-13 | 2015-12-29 | Sanofi | Process for preparation of dronedarone by removal of hydroxyl group |
US9249119B2 (en) | 2012-02-14 | 2016-02-02 | Sanofi | Process for the preparation of dronedarone by oxidation of a sulphenyl group |
-
2010
- 2010-03-30 FR FR1052334A patent/FR2958290B1/fr not_active Expired - Fee Related
-
2011
- 2011-03-30 AU AU2011236671A patent/AU2011236671A1/en not_active Abandoned
- 2011-03-30 US US13/638,500 patent/US9334254B2/en active Active
- 2011-03-30 CN CN201180026858XA patent/CN102933568A/zh active Pending
- 2011-03-30 CA CA2794436A patent/CA2794436A1/fr not_active Abandoned
- 2011-03-30 SG SG2012071965A patent/SG184315A1/en unknown
- 2011-03-30 WO PCT/FR2011/050707 patent/WO2011124827A1/fr active Application Filing
- 2011-03-30 KR KR1020127028218A patent/KR20130018809A/ko not_active Application Discontinuation
- 2011-03-30 EP EP11720315A patent/EP2552899A1/fr not_active Withdrawn
- 2011-03-30 BR BR112012024792A patent/BR112012024792A2/pt not_active IP Right Cessation
- 2011-03-30 RU RU2012146086/04A patent/RU2012146086A/ru not_active Application Discontinuation
- 2011-03-30 MX MX2012011344A patent/MX2012011344A/es not_active Application Discontinuation
- 2011-03-30 JP JP2013501913A patent/JP2013523699A/ja not_active Withdrawn
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2012
- 2012-09-27 IL IL222191A patent/IL222191A0/en unknown
Patent Citations (3)
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EP0471609A1 (fr) | 1990-08-06 | 1992-02-19 | Sanofi | Dérivés de Benzofuranne, Benzothiophène, Indole ou Indolizine, leur procédé de préparation ainsi que les compositions les contenant |
WO2002048132A1 (fr) | 2000-12-11 | 2002-06-20 | Sanofi-Synthelabo | Derive de methanesulfonamido-benzofurane, son procede de preparation et son utilisation comme intermediaire de synthese |
WO2007133637A2 (fr) * | 2006-05-10 | 2007-11-22 | Renovis, Inc. | Dérivés d'amides en tant que ligands de canal ionique et compositions pharmaceutiques et méthodes d'utilisation desdits dérivés |
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ALCARAZ, LILIAN ET AL: "Novel N-aryl and N-heteroaryl sulfamide synthesis via palladium cross-coupling", ORGANIC LETTERS, vol. 6, no. 16, 2004, pages 2705 - 2708, XP002617404 * |
ANJANAPPA, PRAKASH ET AL: "2-(Trimethylsilyl)ethanesulfonyl amide as a new ammonia equivalent for palladium-catalyzed amination of aryl halides", TETRAHEDRON LETTERS, vol. 49, no. 31, 2008, pages 4585 - 4587, XP002617405 * |
BURTON, GEORGE ET AL: "Palladium-Catalyzed Intermolecular Coupling of Aryl Chlorides and Sulfonamides under Microwave Irradiation", ORGANIC LETTERS, vol. 5, no. 23, 2003, pages 4373 - 4376, XP002617403 * |
IKAWA, TAKASHI ET AL: "Pd-Catalyzed Amidations of Aryl Chlorides Using Monodentate Biaryl Phosphine Ligands: A Kinetic, Computational, and Synthetic Investigation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 129, no. 43, 2007, pages 13001 - 13007, XP002617406 * |
YIN, JINGJUN ET AL: "Palladium-catalyzed intermolecular coupling of aryl halides and amides", ORGANIC LETTERS, vol. 2, no. 8, 2000, pages 1101 - 1104, XP002617407 * |
YIN, JINGJUN ET AL: "Pd-Catalyzed Intermolecular Amidation of Aryl Halides: The Discovery that Xantphos Can Be Trans-Chelating in a Palladium Complex", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 124, no. 21, 2002, pages 6043 - 6048, XP002617408 * |
Also Published As
Publication number | Publication date |
---|---|
FR2958290B1 (fr) | 2012-10-19 |
JP2013523699A (ja) | 2013-06-17 |
BR112012024792A2 (pt) | 2015-09-15 |
KR20130018809A (ko) | 2013-02-25 |
US20130023678A1 (en) | 2013-01-24 |
CA2794436A1 (fr) | 2011-10-13 |
AU2011236671A1 (en) | 2012-10-25 |
SG184315A1 (en) | 2012-11-29 |
FR2958290A1 (fr) | 2011-10-07 |
EP2552899A1 (fr) | 2013-02-06 |
AU2011236671A2 (en) | 2013-08-15 |
IL222191A0 (en) | 2012-12-31 |
US9334254B2 (en) | 2016-05-10 |
MX2012011344A (es) | 2013-03-07 |
RU2012146086A (ru) | 2014-05-10 |
CN102933568A (zh) | 2013-02-13 |
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