Reaktion #159446

Reaktionsgleichung

tris(3-sulfophenyl)phosphine trisodium salt

4-chloro-3-methylphenyl boronic acid

3-(5-bromo-2-ethyl-phenyl)-bicyclo[3.2.1]octane-2,4-dione

potassium phosphate

→

3-(4′-chloro-4-ethyl-3′-methylbiphen-3-yl)bicyclo[3.2.1]octane-2,4-dione

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISTILLATIONdistilled water (1.6 ml, 1:1 ratio)
2. 2
   workup.ADDITIONis next added (
3. 3
   Waschenwashing-down any solids from the slides of the vial),
4. 4
   Sonstigeflushing with nitrogen
5. 5
   TemperaturAfter cooling to room temperature the reaction mixture
6. 6
   workup.ADDITIONis diluted with N,N-dimethylformamide (1 ml)
7. 7
   Sonstigepartitioned between 2M hydrochloric acid and dichloromethane
8. 8
   SonstigeAfter the organic phase is separated the aqueous phase
9. 9
   Waschenis again washed with dichloromethane
10. 10
    Einengenconcentrated in vacuo
11. 11
    Sonstigeto afford a crude gum
12. 12
    SonstigeThis crude product is then purified by preparative reverse-phase HPLC

Vorschrift

To a microwave vial is added palladium(II) acetate (3.7 mg, 0.016 mmol), tris(3-sulfophenyl)phosphine trisodium salt (23 mg, 0.041 mmol), 4-chloro-3-methylphenyl boronic acid (0.167 g, 0.97 mmol), 3-(5-bromo-2-ethyl-phenyl)-bicyclo[3.2.1]octane-2,4-dione (0.209 g, 0.65 mmol) and potassium phosphate (0.691 g, 3.26 mmol). A degassed mixed solution of acetonitrile/distilled water (1.6 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 nitrogen. 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 N,N-dimethylformamide (1 ml), then partitioned between 2M hydrochloric acid and dichloromethane. After the organic phase is separated the aqueous phase is again washed with dichloromethane, then all organic fractions are combined and concentrated in vacuo to afford a crude gum. This crude product is then purified by preparative reverse-phase HPLC to afford 3-(4′-chloro-4-ethyl-3′-methylbiphen-3-yl)bicyclo[3.2.1]octane-2,4-dione.

Quelle