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

HRID 1797302ノート

反応式

HRID 1797302 の反応式
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]

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 4

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e5ecc4e888d04b2e8fbe7ba37f5302f0
出典データセット
uspto-grants-2006_04
特許番号
US07034015B2

反応ノート

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