Cesium carbonate → 3-{[2-({3-Chloro-4-[(2-methylphenyl)carbonyl]phenyl}amino)phenyl]ethyl}-1-methylimidazolidine-2,4-dione

HRID 1797327

反応式

HRID 1797327 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[O:9])=[C:4]([Cl:17])[CH:3]=1.Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][CH2:26][N:27]1[C:31](=[O:32])[CH2:30][N:29]([CH3:33])[C:28]1=[O:34].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=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:17][C:4]1[CH:3]=[C:2]([NH:1][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH2:25][CH2:26][N:27]2[C:31](=[O:32])[CH2:30][N:29]([CH3:33])[C:28]2=[O:34])[CH:7]=[CH:6][C:5]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:9]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 98573943-[2-(2-Bromophenyl)ethyl]-1-methylimidazolidine-2,4-dioneHCID 10988565(4-amino-2-chlorophenyl)(2-methylphenyl)Methanone

生成物 1

HCID 210271433-{[2-({3-Chloro-4-[(2-methylphenyl)carbonyl]phenyl}amino)phenyl]ethyl}-1-methylimidazolidine-2,4-dione

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

A mixture of (4-amino-2-chlorophenyl)(2-methylphenyl)methanone (61 mg. 0.25 mmol) (disclosed in WO 01/42189 A1), compound 436 (89 mg, 0.30 mmol), BINAP (5 mg), Pd2(dba)3 (5 mg) and Cs2CO3 (114 mg, 0.35 mmol) in 1,4-dioxane (5 ml) was heated to 120° C. under stirring for 3 days. The reaction mixture was filtered. The obtained solution was concentrated in vacuo. The residue was purified by chromatography (petroleum ether/ethyl acetate 1:1) to provide the desired product, which was not pure. The impure product was further purified by preparative TLC (petroleum ether/ethyl acetate 2:1) to give the pure title compound as brownish oil.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe obtained solution was concentrated in vacuo
  3. customThe residue was purified by chromatography (petroleum ether/ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-8c01a3d927a24472a597fc8e4b75397c
出典データセット
uspto-grants-2006_04
特許番号
US07034015B2

関連ノート

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