N-bromobutanimide → 6-Bromo-4H-furo[3,2-b]pyrrole-5-carboxylic acid methyl ester

HRID 1363300ノート

反応式

HRID 1363300 の反応式
[O:1]1[C:8]2[CH:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[NH:5][C:4]=2[CH:3]=[CH:2]1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1C(=O)N([Br:38])C(=O)C1>C(Cl)Cl>[Br:38][C:7]1[C:8]2[O:1][CH:2]=[CH:3][C:4]=2[NH:5][C:6]=1[C:9]([O:11][CH3:12])=[O:10]

参加物

5

反応物 3

HCID 67184N-bromobutanimideHCID 2724141Tetrabutylammonium FluorideHCID 5082263methyl 4H-furo[3,2-b]pyrrole-5-carboxylate

生成物 1

HCID 596486446-Bromo-4H-furo[3,2-b]pyrrole-5-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a cold solution (ice-water bath) of methyl 4H-furo[3,2-b]pyrrole-5-carboxylate (1.0 g, 6.05 mmol) in DCM (10 mL) was added TBAF (1.0 M in THF, 9.0 mL, 9.0 mmol) and NBS (1.5 g, 7.9 mmol). The resulting dark colored solution was stirred from 0° C. to rt overnight. The reaction mixture was diluted with 50 mL of CH2Cl2 and washed with water (100 mL) and brine (100 mL) and dried (Na2SO4). After filtration, the filtrate was concentrated by evaporation and the crude product was purified by silica gel chromatography (0-5% EtOAc/hexane) to afford a white solid. 1H NMR (400 MHz, CDCl3) δ (ppm) 8.84 (broad, 1H, NH), 7.54 (d, J=2.2 Hz, 1H), 6.48 (d, J=1.83 Hz, 1H), 3.92 (s, 3H) ppm; m+/z 244 (100%), 246 (100%).

後処理

  1. washwashed with water (100 mL) and brine (100 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated by evaporation
  5. customthe crude product was purified by silica gel chromatography (0-5% EtOAc/hexane)
  6. customto afford a white solid

出典と根拠

ORDレコード
ord-05c46f1a29ae460fbb5ba364793e2caf
出典データセット
uspto-grants-2011_02
特許番号
US07884124B2

反応ノート

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