Cesium carbonate → 5-(1-Methyl-propenyl)-pyridin-2-ylamine

Temperature

90 °C

A reaction flask was charged with 0.5 g (2.27 mmol) of 5-(4,4,5,5-tetramethyl-[1,3,2]dioxa borolan-2-yl)-pyridin-2-ylamine, 0.31 g (2.50 mmol) of 2-bromo-but-2-ene, 1.48 g (4.54 mmol) of Cs2CO3 and 52 mg (0.045 mmol) of tetrakis(triphenylphosphine)palladium under nitrogen atmosphere. The solids were dissolved in a degassed toluene/ethanol mixture (20 mL, 1/1) and the reaction heated to 90° C. for 7 h. The reaction was quenched with water (5 mL) and TBME (5 mL). The reaction mixture was filtered. The filtrate was extracted with TBME (20 mL). The organic extract was washed with brine and concentrated under reduced pressure. The residue was purified twice by column chromatography (silica, eluent DCM, 0-50% ethyl acetate) to afford 134 mg of 5-(1-methyl-propenyl)-pyridin-2-ylamine. ES−MS: m/z 149 [M+H+];

1. customThe reaction was quenched with water (5 mL) and TBME (5 mL)
2. filtrationThe reaction mixture was filtered
3. extractionThe filtrate was extracted with TBME (20 mL)
4. extractionThe organic extract
5. washwas washed with brine
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified twice by column chromatography (silica, eluent DCM, 0-50% ethyl acetate)

ORD record

ord-92f7ce7dab264ba5b5c0c9c9c8d441ea

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173638B2