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

HRID 1435769

반응식

HRID 1435769 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 2734571Scandium(III) triflate촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-cde501814ea04cdcaf519af11469670b
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07618967B2

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