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-dedcae7188154dedb9299d12490d5220

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889668B2