Potassium Carbonate → N-(7-(2-chlorophenyl)-5-ethynyl-2,6-naphthyridin-3-yl)cyclopropanecarboxamide

Temperatur

50 °C

A mixture of N-(5-chloro-7-(2-chlorophenyl)-2,6-naphthyridin-3-yl)cyclopropanecarboxamide (110 mg, 0.31 mmol), (trimethylsilyl)acetylene (45 mg, 0.46 mmol), N,N-diisopropylethylamine (0.1 mL, 0.61 mmol), copper(I) iodide (6 mg, 0.03 mmol), and bis(triphenylphosphine)palladium(II) chloride (15 mg, 0.02 mmol) in 1,4-dioxane (2 mL) was heated at 50° C. for 1 hour. The cooled reaction mixture was diluted with ethyl acetate (100 mL) and washed with water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was redissolved in methanol (4 mL) and treated with potassium carbonate (210 mg, 1.5 mmol). The reaction mixture was stirred at room temperature for 1 h, and then diluted with dichloromethane (100 mL) and washed with water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 12 g, ISCO, 0-50% ethyl acetate in heptane) to afford the title compound as a pale yellow solid (50 mg, 50%), which was used in the next step without further purification.

1. customThe cooled reaction mixture
2. washwashed with water (100 mL)
3. customThe organic layer was separated
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. customevaporated in vacuo
7. customto afford a residue that
8. washwashed with water (100 mL)
9. customThe organic layer was separated
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. customevaporated in vacuo
13. customto afford a residue that
14. customwas purified by flash chromatography (silica, 12 g, ISCO, 0-50% ethyl acetate in heptane)

ORD-Eintrag

ord-6e36e90224c748ad88a8ab8ce45c6792

Quelldatensatz

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09206175B2