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

HRID 1797302노트

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HRID 1797302 반응식
Br[C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[CH3:37])=[O:30])=[C:25]([Cl:38])[CH:24]=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.O.CCOC(C)=O.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:38][C:25]1[CH:24]=[C:23]([NH:22][C:2]2[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=2[CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][O:11][CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:28]=[CH:27][C:26]=1[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37])=[O:30]

참가 물질

9

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 99469012-(2-(2-((2-Bromobenzyl)oxy)ethoxy)ethoxy)tetrahydro-2H-pyranHCID 10988565(4-amino-2-chlorophenyl)(2-methylphenyl)Methanone

생성물 1

HCID 10118970(2-Chloro-4-{[2-({2-[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy]ethoxy}methyl)phenyl]amino}phenyl)(2-methylphenyl)methanone

시약·촉매·용매 4

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

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온도
100 °C

실험 절차

Compound 420 (3.39 g, 10.3 mmol) was dissolved in 15 mL dry 1,4-dioxane in a schlenk tube under an argon atmosphere. (4-Amino-2-chlorophenyl)(2-methylphenyl)methanone (disclosed in WO 01/42189) was added and dissolved in the solvent. Rac-BINAP (0.26 g, 0.42 mmol), Pd2(dba)3 (0.19 g, 0.20 mmol) and Cs2CO3 (4.7 g, 14.4 mmol) were added, and the reaction mixture was stirred under an argon atmosphere at 100° C. for 18 h. The reaction mixture was diluted with H2O and EtOAc, and the water phase was extracted twice with EtOAc. The combined organic phases were washed with brine, dried (MgSO4) and evaporated in vacuo. The crude product was purified by flash chromatography using DCM/acetone 100:1 as the eluent to afford the title compound as an oil.

후처리

  1. dissolutiondissolved in the solvent
  2. extractionthe water phase was extracted twice with EtOAc
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash chromatography

출처 및 근거

ORD 기록
ord-e5ecc4e888d04b2e8fbe7ba37f5302f0
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07034015B2

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