Reaktion #42312

Reaktionsgleichung

methyl 3-[(dipropylamino)carbonyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

4-bromobenzenedimethyl-sulfonamide

sodium carbonate

→

methyl 4′-[(dimethylamino)sulfonyl]-5-[(dipropylamino)carbonyl][1,1′-biphenyl]-3-carboxylate

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeis degassed under reduced pressure for 15 minutes
2. 2
   Sonstigepurged with argon
3. 3
   Sonstigethe reaction mixture is degassed under reduced pressure for 15 minutes
4. 4
   Sonstigepurged with argon
5. 5
   TemperaturThe reaction mixture is heated
6. 6
   Temperaturat reflux for 4 hours
7. 7
   Filtration, filtered through a plug of diatomaceous earth and sodium sulfate
8. 8
   Einengenthe filtrate is concentrated under reduced pressure
9. 9
   SonstigePurification by flash column chromatography (silica; ethyl acetate/hexanes, 1/1)

Vorschrift

A mixture of methyl 3-[(dipropylamino)carbonyl]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Step 1, 534 mg, 1.4 mmol), 4-bromobenzenedimethyl-sulfonamide (363 mg, 1.4 mmol), and sodium carbonate (2 mL of a 2 M mixture in water, 4.1 mmol) in toluene (10 mL) is degassed under reduced pressure for 15 minutes and then purged with argon. Palladium tetrakis(triphenylphosphine) (40 mg, 0.025 mmol) is added and the reaction mixture is degassed under reduced pressure for 15 minutes and then purged with argon. The reaction mixture is heated at reflux for 4 hours, cooled to 20-25 degrees C., filtered through a plug of diatomaceous earth and sodium sulfate, and the filtrate is concentrated under reduced pressure. Purification by flash column chromatography (silica; ethyl acetate/hexanes, 1/1) gives methyl 4′-[(dimethylamino)sulfonyl]-5-[(dipropylamino)carbonyl][1,1′-biphenyl]-3-carboxylate (XXXVIII), ESI-MS (m/z) [M+H]+=447.

Quelle