Cesium carbonate → ethyl (2E)-3-(6-{[(3R)-1-benzyl-3-pyrrolidinyl]amino}-3-pyridyl)acrylate

Temperature

95 °C

To a solution of ethyl (2E)-3-(6-chloro-3-pyridyl)acrylate (14.3 g) in dioxane (140 mL) was added palladium(II) acetate (1.52 g), 2′-(dicyclohexylphosphino)-N,N-dimethyl-2-biphenylamine (3.99 g), cesium carbonate (30.2 g), and (3R)-(−)-1-benzyl-3-aminopyrrolidine (13.1 g), and the mixture was heated at 95° C. for 2.5 days. The resulting mixture was poured into sat.NH4Cl aqueous solution and extracted with AcOEt. The organic layer was washed with sat. NH4Cl aq solution, water, and brine, and dried over Na2SO4. The solvent was removed in vacuo and residual brown oil was purified by silica gel column chromatography eluted with AcOEt to give ethyl (2E)-3-(6-{[(3R)-1-benzyl-3-pyrrolidinyl]amino}-3-pyridyl)acrylate as pale yellow oil (10.7 g)

1. additionThe resulting mixture was poured
2. extractionNH4Cl aqueous solution and extracted with AcOEt
3. washThe organic layer was washed with sat. NH4Cl aq solution, water, and brine
4. dry with materialdried over Na2SO4
5. customThe solvent was removed in vacuo and residual brown oil
6. customwas purified by silica gel column chromatography
7. washeluted with AcOEt

ORD record

ord-343672d13e874fa28565a7a7d0868aa8

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465731B2