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

HRID 1593425ノート

反応式

HRID 1593425 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b6f7d3321f9b45a2b153cfbbc4029f4f
出典データセット
uspto-grants-2007_11
特許番号
US07297694B2

反応ノート

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