Cesium carbonate → [2-Chloro-4-(2-nitro-phenylamino)-phenyl]-{2-methyl-4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-methanone

HRID 1012606

반응식

HRID 1012606 반응식
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][O:31]3)=[CH:22][C:21]=2[CH3:36])=[O:19])=[C:14]([Cl:37])[CH:13]=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].O.CCOC(C)=O>[Cl:37][C:14]1[CH:13]=[C:12]([NH:11][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH:17]=[CH:16][C:15]=1[C:18]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)=[CH:22][C:21]=1[CH3:36])=[O:19]

참가 물질

9

반응물 4

HCID 10796Cesium carbonateHCID 69115o-IodonitrobenzeneHCID 634876Binap, (A+-)-HCID 67313818(4-Amino-2-chloro-phenyl)-{2-methyl-4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-methanone

생성물 1

HCID 58677600[2-Chloro-4-(2-nitro-phenylamino)-phenyl]-{2-methyl-4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-methanone

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

1-Iodo-2-nitro-benzene (1.38 g, 5.54 mmol) was dissolved in 40 mL dry 1,4-dioxane under an argon atmosphere. Compound 471 (1.77 g, 4.54 mmol) was added and dissolved in the solvent. Rac-BINAP (106 mg, 0.17 mmol), Pd2(dba)3 (104 mg, 0.11 mmol) and Cs2CO3 (2.07 g, 6.30 mmol) were added, and the reaction mixture was stirred under an argon atmosphere at 100° C. for 24 h. The reaction mixture was poured into a mixture of EtOAc and water. The aqueous phase was washed with more EtOAc. The organic phases were combined and washed with brine, dried (MgSO4), filtered and then purified by flash chromatography using EtOAc/petroleum ether 1:5 as the eluent to afford the title compound.

후처리

  1. dissolutiondissolved in the solvent
  2. washThe aqueous phase was washed with more EtOAc
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-31eda029c34f465c90e975136b229a9d
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977387B2

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