反应详情

A round-bottom flask was charged with perfluorophenyl 5-(pyrrolidin-2-yl)naphthalene-2-sulfonate 2,2,2-trifluoroacetate (0.234 g, 0.420 mmol), N-(2,4-dimethoxybenzyl)thiazol-2-amine (0.126 g, 0.504 mmol), and THF (4.20 ml) to give a clear solution. The flask was cooled in an dry ice-acetone bath for 10 min, then lithium bis(trimethylsilyl)amide (1M in THF) (0.924 ml, 0.924 mmol) was added dropwise over 30 seconds. The reaction was stirred for 30 minutes, then the cooling bath was removed and the reaction was stirred for 30 minutes. The mixture was diluted with saturated aq. ammonium chloride solution, then extracted with EtOAc (2×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (12-g, 0 to 10% MeOH/DCM) to give N-(2,4-dimethoxybenzyl)-5-(pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide as a white foam. (ESI) 510.2 (M+H)+.

1. customto give a clear solution
2. temperatureThe flask was cooled in an dry ice-acetone bath for 10 min
3. customthe cooling bath was removed
4. stirringthe reaction was stirred for 30 minutes
5. additionThe mixture was diluted with saturated aq. ammonium chloride solution
6. extractionextracted with EtOAc (2×)
7. dry with materialThe combined organic extracts were dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customThe residue was purified by chromatography on silica gel (12-g, 0 to 10% MeOH/DCM)