Sodium Carbonate → N-{4-[1-ethyl-3-(2-thienyl)-1H-pyrazol-4-yl]pyridin-2-yl}propanamide

N-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]propanamide (0.60 mmol) and bis(tricyclohexylphosphine)palladium(II) chloride (0.05 mmol) were weighed into a microwave vial (reaction volume 2-5 mL). A solution of 1-ethyl-4-iodo-3-(2-thienyl)-1H-pyrazole (0.50 mmol) in 3.3 mL degassed dioxane and 1.1 mL of a degassed 2 M aqueous sodium carbonate solution were added. The reaction mixture was purged with argon, the microwave vial was capped with a septum and transferred to a laboratory microwave oven. The reaction mixture was irradiated to a reaction temperature of 120° C. for 15 min. After cooling to room temperature, the reaction mixture was diluted with water and extracted with dichloromethane. The combined organic phases were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by chromatography on silica gel (cyclohexane:ethyl acetate 95:5 to 0:100) to afford 152 mg N-{4-[1-ethyl-3-(2-thienyl)-1H-pyrazol-4-yl]pyridin-2-yl}propanamide (93% yield).

1. additionwere added
2. customThe reaction mixture was purged with argon
3. customthe microwave vial was capped with a septum
4. customtransferred to a laboratory microwave oven
5. customThe reaction mixture was irradiated to a reaction temperature of 120° C. for 15 min
6. additionthe reaction mixture was diluted with water
7. extractionextracted with dichloromethane
8. washThe combined organic phases were washed with brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated
12. customThe residue was purified by chromatography on silica gel (cyclohexane:ethyl acetate 95:5 to 0:100)

ORD record

ord-f1671475fdf04f96bfaecd27f7d54da3

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08685974B2