Water → HCID 178524221, Verbindung

Under an atmosphere of nitrogen, a solution of 5-bromo-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid (Example 9 d, 0.4 g, 1.5 mmol), 1H-pyrazol-3-ylboronic acid (CAN 376584-63-3, 0.2 g, 1.8 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464-05-4, 60 mg, 0.07 mmol) and sodium carbonate (1.3 g, 12 mmol) in DMF (10 mL) was heated to 100° C. for 5 h. The reaction mixture was poured into water and extracted with ethyl acetate (30 mL). The aqueous layer was adjusted to pH=2 by addition of 1 N hydrochloric acid and the resulting mixture was extracted with ethyl acetate (3×30 mL). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography (silica gel, 15 g, eluting with 30% ethyl acetate in petroleum ether) to yield the title compound (0.23 g, 1 mmol, 60.3%) as white solid; MS (EI): m/e 260.1 [M+H]+.

1. customwas heated to 100° C. for 5 h
2. extractionextracted with ethyl acetate (30 mL)
3. additionThe aqueous layer was adjusted to pH=2 by addition of 1 N hydrochloric acid
4. extractionthe resulting mixture was extracted with ethyl acetate (3×30 mL)
5. washThe combined organic extracts were washed with water and brine
6. dry with materialdried over anhydrous sodium sulfate
7. customevaporated
8. customThe residue was purified by column chromatography (silica gel, 15 g, eluting with 30% ethyl acetate in petroleum ether)

ORD-Eintrag

ord-f95c0132d282452b8245fb3c241d99de

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09290451B2