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

HRID 381505노트

반응식

HRID 381505 반응식
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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0b81452e6c5d46ee9e348642ae47609f
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306891B1

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