Reaktion #477964

Reaktionsgleichung

tert-butyl 2-(benzofuran-2-carbonylamino)-4-(trifluoromethylsulfonyloxy)thiophene-3-carboxylate

sodium carbonate

ethanol

4-methyl-3-nitrophenylboronic acid

→

84

Ausbeute 81.7%

2-(benzofuran-2-carbonylamino)-4-(4-methyl-3-nitro-phenyl)thiophene-3-carboxylic acid

Ausbeute 81.7%

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe mixture was filtered through Celite
2. 2
   Waschenthe Celite rinsed with methylene chloride
3. 3
   WaschenThe organic fraction of the filtrate was washed with water
4. 4
   Trocknendried with sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   Sonstigetriturated in methanol
8. 8
   Sonstigedecanted
9. 9
   Sonstigethe resulting solid was dried under vacuum
10. 10
    workup.ADDITIONtreated with a 1:1 mixture of methylene chloride and trifluoroacetic acid
11. 11
    EinengenAfter 4 hours the mixture was concentrated in vacuo
12. 12
    Sonstigethe residue triturated in methylene chloride
13. 13
    Sonstigedecanted
14. 14
    Sonstigedried under high vacuum

Vorschrift

tert-butyl 2-(benzofuran-2-carbonylamino)-4-(trifluoromethylsulfonyloxy)thiophene-3-carboxylate (82, 50 mg, 0.102 mmol), 4-methyl-3-nitrophenylboronic acid (28 mg, 0.153 mmol), Tetrakis(triphenylphosphine)palladium(0) (1.0 mg, 0.001 mmol), and sodium carbonate (42 mg, 0.407 mmol), were combined in 2:1:1 ethanol, toluene and water the biphasic mixture was stirred vigorously in sealed vial at 70 C. After 2 hours, the mixture was filtered through Celite and the Celite rinsed with methylene chloride. The organic fraction of the filtrate was washed with water, dried with sodium sulfate, filtered, concentrated, triturated in methanol, centrifuged, decanted and the resulting solid was dried under vacuum and treated with a 1:1 mixture of methylene chloride and trifluoroacetic acid. After 4 hours the mixture was concentrated in vacuo, and the residue triturated in methylene chloride, centrifuged, decanted and dried under high vacuum to give 84 as a white powder (35.2 mg, 43%). 1H NMR (500 MHz, DMSO d6) δ=13.48 (br, 1 H), 12.57 (br, 1 H), 7.96 (s, 1 H), 7.86 (m, 2 H), 7.76 (d, 1 H), 7.64 (d, 1 H), 7.57 (t, 1 H), 7.49 (d, 1 H), 7.42 (t, 1 H), 2.55 (s, 3 H) ppm.

Quelle