Potassium Phosphate, Tribasic → HCID 68487701, Verbindung

Temperatur

160 °C

To a microwave vial is added palladium(II) acetate (3.3 mg, 0.015 mmol), tris(3-sulfophenyl)phosphine trisodium salt (22 mg, 0.038 mmol), 4-chloro-3-trifluoromethylphenyl boronic acid (0.200 g, 0.89 mmol), 4-(5-bromo-2-ethylphenyl)-2,2,6,6-tetramethylpyran-3,5-dione (0.208 g, 0.59 mmol) and potassium phosphate (0.625 g, 2.95 mmol). A degassed mixed solution of acetonitrile/distilled water (1.5 ml, 1:1 ratio) is next added (washing-down any solids from the slides of the vial), followed by stirring for 5 minutes and flushing with argon. This mixture is then heated at 160° C. under microwave irradiation for 15 minutes. After cooling to room temperature the reaction mixture is diluted with ethyl acetate (3 ml) and acidified to pH2 with dilute aqueous hydrochloric acid. The organic phase is separated and the aqueous phase is further extracted with ethyl acetate (2×3 ml). All organics are then combined, filtered through a silica plug and evaporated to give a crude product which is dissolved in N,N-dimethylformamide (2.5 ml) and purified by preparative reverse phase HPLC to afford 4-(4′-chloro-4-ethyl-3′-trifluoromethylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.143 g) as a white powder.

1. distillationdistilled water (1.5 ml, 1:1 ratio)
2. additionis next added (
3. washwashing-down any solids from the slides of the vial),
4. customflushing with argon
5. temperatureAfter cooling to room temperature the reaction mixture
6. additionis diluted with ethyl acetate (3 ml)
7. customThe organic phase is separated
8. extractionthe aqueous phase is further extracted with ethyl acetate (2×3 ml)
9. filtrationfiltered through a silica plug
10. customevaporated
11. customto give a crude product which
12. custompurified by preparative reverse phase HPLC

ORD-Eintrag

ord-e2daa8123b32425eb52f5c2aac8f65b7

Quelldatensatz

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08680012B2