Reaktion #170209

Reaktionsgleichung

tert-Butyl acrylate

diisopropylethylamine

P(o-tolyl)3

5-bromo-1H-pyrrolo[2,3-b]pyridine

→

title compound

(E)-tert-Butyl 3-(1H-pyrrolo[2,3-b]pyridin-5-yl)acrylate t-butyl acrylate

Lösungsmittel

propionitrile

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting mixture was purged with argon
2. 2
   SonstigeThe mixture was then purged with argon a second time
3. 3
   Temperaturrefluxed overnight
4. 4
   FiltrationThe reaction mixture was filtered on Celite®
5. 5
   EinengenThe filtrate was concentrated to dryness
6. 6
   WaschenThe organic layers were washed with a saturated solution of sodium chloride (3×50 mL)
7. 7
   Trocknendried over sodium sulfate
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated to dryness
10. 10
    SonstigeThe crude was purified by flash chromatography on silica gel

Vorschrift

tert-Butyl acrylate (5.9 mL, 40.6 mmol), diisopropylethylamine (3.5 mL, 20.3 mmol) and P(o-tolyl)3 (618 mg, 2.0 mmol) were successively added to a suspension of 5-bromo-1H-pyrrolo[2,3-b]pyridine (2.0 g, 10.15 mmol) in propionitrile (40 mL) and dimethylformamide (10 mL). The resulting mixture was purged with argon prior to the addition of palladium acetate (227 mg, 1.0 mmol). The mixture was then purged with argon a second time and refluxed overnight. The reaction mixture was filtered on Celite®. The filtrate was concentrated to dryness and the residue was solubilized in ethyl acetate (3×100 mL). The organic layers were washed with a saturated solution of sodium chloride (3×50 mL), dried over sodium sulfate, filtered and concentrated to dryness. The crude was purified by flash chromatography on silica gel using dichloromethane/ethyl acetate (1:0 to 7:3) as eluent. The title compound was obtained as a yellow solid (465 mg, 28%)

Quelle