Potassium Phosphate, Tribasic → HCID 68484223, compound

Temperature

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-2-methylphenyl boronic acid (0.152 g, 0.89 mmol), 4-(5-bromo-2-ethyl-phenyl)-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-2′-methylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (0.139 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 record

ord-ac45c0326b424998b0d55fa7781ca8a6

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09006429B2