Potassium Carbonate → HCID 59606547, compound

A mixture of 3-bromo-2-methylpyridine (0.13 mL; 1.16 mmol; 1 eq.), methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (353 mg; 1.28 mmol; 1.1 eq.), potassium carbonate (803 mg; 5.81 mmol; 5 eq.) and tetrakis(triphenylphosphine)palladium(0) (134 mg; 0.12 mmol; 0.1 eq.) in toluene (1 mL) and water (1 mL) was refluxed for 2 hours. The reaction mixture was cooled down to room temperature and filtered through a pad of Celite® which was further washed with toluene (20 mL). The filtrate was concentrated in vacuo and the residue taken up in Ethyl acetate (10 mL). The organic layer was washed with a sat. aq. NaHCO3, water and brine, dried over MgSO4 and concentrated in vacuo. The residue (250 mg; 1.04 mmol; 1 eq.) was taken up in EtOH (7.5 mL) and sodium hydroxide (5M; 0.62 mL; 3.11 mmol; 3 eq.). The reaction mixture was stirred at 60° C. for 2 hours then concentrated in vacuo. The residue was taken up in water (50 mL) and the aqueous phase was washed with Ethyl acetate (2×20 mL) then acidified pH 2 with conc. HCl. The solution was concentrated in vacuo to ca. 15 mL, the precipitate filtered off and washed with ACN to afford the title compound (190 mg, 72%) as a beige solid.

1. temperaturewas refluxed for 2 hours
2. filtrationfiltered through a pad of Celite® which
3. washwas further washed with toluene (20 mL)
4. concentrationThe filtrate was concentrated in vacuo
5. washThe organic layer was washed with a sat. aq. NaHCO3, water and brine
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo
8. concentrationthen concentrated in vacuo
9. washthe aqueous phase was washed with Ethyl acetate (2×20 mL)
10. concentrationThe solution was concentrated in vacuo to ca. 15 mL
11. filtrationthe precipitate filtered off
12. washwashed with ACN

ORD record

ord-61d6707e84b7483a9c25eb3ea1924959

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404676B2