4-Chloro-2-toluidine → [2-Chloro-4-(4-chloro-2-methyl-phenylamino)-phenyl]-(2-fluoro-5-hydroxy-phenyl)-methanone

HRID 1012659

반응식

HRID 1012659 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:20]=2[F:26])=[O:18])=[C:13]([Cl:27])[CH:12]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:27][C:13]1[CH:12]=[C:11]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[CH3:9])[CH:16]=[CH:15][C:14]=1[C:17]([C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:20]=1[F:26])=[O:18]

참가 물질

7

반응물 4

HCID 72514-Chloro-2-toluidineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 67314566(4-Bromo-2-chloro-phenyl)-(2-fluoro-5-hydroxy-phenyl)-methanone

생성물 1

HCID 67313338[2-Chloro-4-(4-chloro-2-methyl-phenylamino)-phenyl]-(2-fluoro-5-hydroxy-phenyl)-methanone

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

반응 조건

온도
130 °C

실험 절차

4-Chloro-2-methyl-phenylamine (73 μL, 0.60 mmol) was dissolved in 5 mL dry 1,4-dioxane in a reaction vial under an argon atmosphere. Compound 511 (200 mg, 0.60 mmol) was added and dissolved in the solvent. Rac-BINAP (18 mg, 0.028 mmol), Pd2(dba)3 (17 mg, 0.018 mmol) and Cs2CO3 (277 mg, 0.84 mmol) were added. The reaction vial was flushed with argon, closed and then stirred at 130° C. for 10 min. in a microwave oven. The reaction mixture was filtered through Celite and then purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) (v:v=1:9 to 1:4) as the eluent to afford the title compound as yellow solid. 13C NMR (CDCl3)

후처리

  1. dissolutiondissolved in the solvent
  2. customThe reaction
  3. customvial was flushed with argon
  4. customclosed
  5. filtrationThe reaction mixture was filtered through Celite
  6. custompurified by continuous gradient flash chromatography

출처 및 근거

ORD 기록
ord-9dc428c37975492183a6545d9433f74a
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977387B2

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