反应详情

A solution of tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 2 g, 9.99 mmol), 3-bromo-2-chloro-5-(trifluoromethyl)pyridine (CAS number 71701-92-3; 2.86 g, 10.98 mmol), DIPEA (1.74 ml, 9.99 mmol) in DMSO (35 ml) was heated at 140° C. for 5 hours. The reaction was partitioned between ethyl acetate and water. The phases were separated and the aqueous layer was re-extracted with ethyl acetate (2×50 ml). The combined organics were washed with brine (50 ml), filtered through a hydrophobic frit and concentrated in vacuo. The crude product was purified by column chromatography (silica, 0-50% ethyl acetate/petrol), then by column chromatography (silica, 0-15% ethyl acetate/petrol) and then by column chromatography (silica, 0-10% ethyl acetate/petrol) to afford the title compound.

1. customThe reaction was partitioned between ethyl acetate and water
2. customThe phases were separated
3. extractionthe aqueous layer was re-extracted with ethyl acetate (2×50 ml)
4. washThe combined organics were washed with brine (50 ml)
5. filtrationfiltered through a hydrophobic frit
6. concentrationconcentrated in vacuo
7. customThe crude product was purified by column chromatography (silica, 0-50% ethyl acetate/petrol)