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Cesium carbonate → 3-[2-Chloro-4-(3-fluoro-2-methyl-phenylamino)-benzoyl]-4-methyl-benzoic acid methyl ester

HRID 1012601
ノート
印刷プレビュー

反応式

HRID 1012601 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH3:9].[CH3:10][O:11][C:12](=[O:30])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=2[Cl:28])[CH:14]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:10][O:11][C:12](=[O:30])[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]([C:20](=[O:29])[C:21]2[CH:26]=[CH:25][C:24]([NH:27][C:2]3[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=3[CH3:9])=[CH:23][C:22]=2[Cl:28])[CH:14]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 27363352-Bromo-6-fluorotolueneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 673136853-(4-Amino-2-chlorobenzoyl)-4-methylbenzoic acid methyl ester

生成物 1

HCID 673142013-[2-Chloro-4-(3-fluoro-2-methyl-phenylamino)-benzoyl]-4-methyl-benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

1-Bromo-3-fluoro-2-methyl-benzene (189 mg, 1.0 mmol) was dissolved in 4 mL dry 1,4-dioxane under an argon atmosphere. Compound 402 (304 mg, 1.00 mmol) was added and dissolved in the solvent. Dicyclohexyl-(2′,4′,6′-triisopropyl-biphenyl-2-yl)-phosphane (19 mg, 0.04 mmol), Pd(OAc)2 (5 mg, 0.02 mmol) and Cs2CO3 (407 mg, 1.25 mmol) were added, and the reaction mixture was stirred under an argon atmosphere at 120° C. for 60 h. The reaction mixture was filtered and then purified by flash chromatography using EtOAc/petroleum ether (40-60) 1:4 as the eluent to afford the title compound as a solid. 13C NMR (CDCl3) δ

後処理

  1. dissolutiondissolved in the solvent
  2. filtrationThe reaction mixture was filtered
  3. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-26f2dda1ff8547b8ad446dafee1e7030
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07977387B2

反応ノート

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