Dimethylformamide → 1-[4-dimethylamino-1-(4-fluorobenzyl)-1H-pyrrol-2-yl]ethanone

HRID 381505ノート

反応式

HRID 381505 の反応式
NC1[CH:3]=[C:4]([C:15](=[O:17])[CH3:16])[N:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH:6]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:24][N:25]([CH:27]=O)[CH3:26]>>[CH3:26][N:25]([CH3:24])[C:27]1[CH:3]=[C:4]([C:15](=[O:17])[CH3:16])[N:5]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)[CH:6]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 183635091-[4-amino-1-(4-fluorobenzyl)-1H-pyrrol-2-yl]ethanone

生成物 1

HCID 183634671-[4-dimethylamino-1-(4-fluorobenzyl)-1H-pyrrol-2-yl]ethanone

実験手順

To a 100 mL round bottomed flask with a stirring bar and a nitrogen inlet was added 1-[4-amino-1-(4-fluorobenzyl)-1H-pyrrol-2-yl]ethanone AVI-2-1 (0.50 g, 2.15 mmol), dry DMF (20 mL), finely powdered Cs2CO3 (3.26 g, 10 mmol) and Mel (0.31 mL, 5.00 mmol). The resulting mixture was stirred lh at ambient temperature. The solids were removed by filtration and the solvent was removed in vacuo. The residue was dissolved in EtOAc and washed with water (3×) and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave an oil. This material was chromatographed on silica gel using 50% EtOAc-hexanes as eluant to give 1-[4-dimethylamino-1-(4-fluorobenzyl)-1H-pyrrol-2-yl]ethanone AVI-3-1 as an oil. 1H NMR (CDCl3) δ 2.36 (3H, s), 2.70 (6H, s), 5.46 (2H, s), 6.36 (1H, d, j=2.0 Hz), 6.50 (1H, d, j=2.0 Hz), 6.98 (2H, m), 7.11 (2H, m).

後処理

  1. customThe solids were removed by filtration
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water (3×) and brine
  5. customDrying
  6. filtration(MgSO4), filtration and removal of the solvent in vacuo
  7. customgave an oil
  8. customThis material was chromatographed on silica gel using 50% EtOAc-hexanes as eluant

出典と根拠

ORDレコード
ord-0b81452e6c5d46ee9e348642ae47609f
出典データセット
uspto-grants-2001_10
特許番号
US06306891B1

反応ノート

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