Ethyl Acetate → 3-(7-fluoro-1H-indol-3-yl)-indan-1-one

HRID 1435769

反応式

HRID 1435769 の反応式
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[C:11]1(=[O:20])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12]1.C(OCC)(=O)C>C(Cl)Cl.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Sc+3]>[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[O:20])[CH2:12]1

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 27745047-Fluoro-1H-indoleHCID 118153841H-inden-1-one

生成物 1

HCID 689053033-(7-fluoro-1H-indol-3-yl)-indan-1-one収率 82%

試薬・触媒・溶媒 2

HCID 2734571Scandium(III) triflate触媒HCID 6344Dichloromethane溶媒

実験手順

Triethylamine (4.5 mL; 32 mmol; 1.2 equiv.) was added to 3-bromo-indan-1-one (5.6 g; 27 mmol) in 100 mL THF at 0° C. and stirred 1 h at r.t. The reaction mixture was filtered to remove triethylammonium bromide and concentrated in vacuo to give inden-1-one. 7-Fluoroindole (3.3 g, 22 mmol ) and Sc(OTf)3 (550mg, 5 mol %) were added to inden-1-one in 100 mL CH2Cl2 at 0° C. The reaction mixture was allowed to warm to room temperature over night. 100 mL ethyl acetate was added and the mixture was filtered through a silica gel plug and concentrated in vacuo. After flash chromatography (heptane/ethyl acetate, silica gel) 5.9 g 3-(7-fluoro-1H-indol-3-yl)-indan-1-one (82%) was isolated.

後処理

  1. filtrationthe mixture was filtered through a silica gel plug
  2. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-cde501814ea04cdcaf519af11469670b
出典データセット
uspto-grants-2009_11
特許番号
US07618967B2

関連ノート

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