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

HRID 1012599
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HRID 1012599 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[F: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][C:5]([Cl:8])=[CH:4][C:3]=3[F:9])=[CH:23][C:22]=2[Cl:28])[CH:14]=1
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참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 1372751-Bromo-4-chloro-2-fluorobenzeneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 673136853-(4-Amino-2-chlorobenzoyl)-4-methylbenzoic acid methyl ester

생성물 1

HCID 673145633-[2-Chloro-4-(4-chloro-2-fluoro-phenylamino)-benzoyl]-4-methyl-benzoic acid methyl ester

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매

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온도
120 °C

실험 절차

1-Bromo-4-chloro-2-fluorobenzene (820 μL, 6.58 mmol) was dissolved in 20 mL dry 1,4-dioxane under an argon atmosphere. Compound 402 (2.00 g, 6.58 mmol) was added and dissolved in the solvent. Dicyclohexyl-(2′,4′,6′-triisopropyl-biphenyl-2-yl)-phosphane (125 mg, 0.26 mmol), Pd(OAc)2 (30 mg, 0.13 mmol) and Cs2CO3 (2.68 g, 8.22 mmol) were added, and the reaction mixture was stirred under an argon atmosphere at 120° C. for 48 h. The reaction mixture was filtered and then purified by flash chromatography using EtOAc/petroleum ether (40-60) 1:9 as the eluent to afford the title compound as a solid.

후처리

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

출처 및 근거

ORD 기록
ord-5ce547329f214e6eb907c99b84a80796
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07977387B2

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