4-Chloro-2-toluidine → [2-Chloro-4-(4-chloro-2-methyl-phenylamino)-phenyl]-(2-fluoro-5-hydroxy-phenyl)-methanone

HRID 1012659ノート

反応式

HRID 1012659 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH3:9])[CH:3]=1.Br[C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:20]=2[F:26])=[O:18])=[C:13]([Cl:27])[CH:12]=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]>[Cl:27][C:13]1[CH:12]=[C:11]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[CH3:9])[CH:16]=[CH:15][C:14]=1[C:17]([C:19]1[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:20]=1[F:26])=[O:18]

参加物

7

反応物 4

HCID 72514-Chloro-2-toluidineHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 67314566(4-Bromo-2-chloro-phenyl)-(2-fluoro-5-hydroxy-phenyl)-methanone

生成物 1

HCID 67313338[2-Chloro-4-(4-chloro-2-methyl-phenylamino)-phenyl]-(2-fluoro-5-hydroxy-phenyl)-methanone

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
130 °C

実験手順

4-Chloro-2-methyl-phenylamine (73 μL, 0.60 mmol) was dissolved in 5 mL dry 1,4-dioxane in a reaction vial under an argon atmosphere. Compound 511 (200 mg, 0.60 mmol) was added and dissolved in the solvent. Rac-BINAP (18 mg, 0.028 mmol), Pd2(dba)3 (17 mg, 0.018 mmol) and Cs2CO3 (277 mg, 0.84 mmol) were added. The reaction vial was flushed with argon, closed and then stirred at 130° C. for 10 min. in a microwave oven. The reaction mixture was filtered through Celite and then purified by continuous gradient flash chromatography using EtOAc/petroleum ether (40-60) (v:v=1:9 to 1:4) as the eluent to afford the title compound as yellow solid. 13C NMR (CDCl3)

後処理

  1. dissolutiondissolved in the solvent
  2. customThe reaction
  3. customvial was flushed with argon
  4. customclosed
  5. filtrationThe reaction mixture was filtered through Celite
  6. custompurified by continuous gradient flash chromatography

出典と根拠

ORDレコード
ord-9dc428c37975492183a6545d9433f74a
出典データセット
uspto-grants-2011_07
特許番号
US07977387B2

反応ノート

読み込み中…