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

HRID 1012606

反応式

HRID 1012606 の反応式
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]

参加物

9

反応物 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

生成物 1

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

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.

後処理

  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

出典と根拠

ORDレコード
ord-31eda029c34f465c90e975136b229a9d
出典データセット
uspto-grants-2011_07
特許番号
US07977387B2

関連ノート

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