N-bromobutanimide → 5-(5-Bromo-2-pyridin-4-ylfuran-3-yl)indan-1-one

HRID 1593425노트

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HRID 1593425 반응식
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[O:8][CH:9]=[CH:10][C:11]=2[C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[C:17](=[O:21])[CH2:16][CH2:15]3)=[CH:3][CH:2]=1.[Br:22]N1C(=O)CCC1=O.C(=O)([O-])O.[Na+]>CN(C)C=O>[Br:22][C:9]1[O:8][C:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)=[C:11]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[C:17](=[O:21])[CH2:16][CH2:15]3)[CH:10]=1

참가 물질

5

반응물 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 694314975-(2-Pyridin-4-ylfuran-3-yl)indan-1-one

생성물 1

HCID 694283845-(5-Bromo-2-pyridin-4-ylfuran-3-yl)indan-1-one수율 16%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

A solution of the product of Step 8 (1.0 g, 3.6 mmol) in dry dimethylformamide (10 ml) was treated with freshly recrystallised N-bromosuccinimide (1.42 g, 8.0 mmol) and heated at 50° C. for 1 hour. After cooling to room temperature, the reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution, extracted into dichloromethane, washed twice with brine, dried (MgSO4) and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate to afford the title compound (0.2 g, 16%); 1H NMR (CDCl3) 8.52 (2H, d, J 8 Hz), 7.80 (1H, d, J 11 Hz), 7.49 (1H, s), 7.38 (1H, d, J 8 Hz), 7.32 (2H, d, J 8 Hz), 6.54 (1H, s), 3.17 (2H, t, J 5 Hz), 2.75 (2H, t, 5 Hz).

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionextracted into dichloromethane
  3. washwashed twice with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel eluting with ethyl acetate

출처 및 근거

ORD 기록
ord-b6f7d3321f9b45a2b153cfbbc4029f4f
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297694B2

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