Dimethylformamide → 1-[4-dimethylamino-1-(4-fluorobenzyl)-1H-pyrrol-2-yl]ethanone
Reaction equation
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]=1Participants
Procedure
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).
Workup
- customThe solids were removed by filtration
- customthe solvent was removed in vacuo
- dissolutionThe residue was dissolved in EtOAc
- washwashed with water (3×) and brine
- customDrying
- filtration(MgSO4), filtration and removal of the solvent in vacuo
- customgave an oil
- customThis material was chromatographed on silica gel using 50% EtOAc-hexanes as eluant
Sources & evidence
- ORD record
- ord-0b81452e6c5d46ee9e348642ae47609f
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06306891B1
Reaction notes
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